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<span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-N,N-dialkylhydrazones" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#N,N-dialkylhydrazones"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span><i>N</i>,<i>N</i>-dialkylhydrazones</span> </div> </a> <ul id="toc-N,N-dialkylhydrazones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Recovery_of_carbonyl_compounds_from_N,N-dialkylhydrazones" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Recovery_of_carbonyl_compounds_from_N,N-dialkylhydrazones"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Recovery of carbonyl compounds from N,N-dialkylhydrazones</span> </div> </a> <ul id="toc-Recovery_of_carbonyl_compounds_from_N,N-dialkylhydrazones-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gallery" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Gallery"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Gallery</span> </div> </a> <ul id="toc-Gallery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" 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href="https://ca.wikipedia.org/wiki/Hidrazona" title="Hidrazona – Catalan" lang="ca" hreflang="ca" data-title="Hidrazona" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Hydrazony" title="Hydrazony – Czech" lang="cs" hreflang="cs" data-title="Hydrazony" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Hydrazone" title="Hydrazone – German" lang="de" hreflang="de" data-title="Hydrazone" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hidrazona" title="Hidrazona – Spanish" lang="es" hreflang="es" data-title="Hidrazona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DB%8C%D8%AF%D8%B1%D8%A7%D8%B2%D9%88%D9%86" title="هیدرازون – Persian" lang="fa" hreflang="fa" data-title="هیدرازون" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Hydrazone" title="Hydrazone – French" lang="fr" hreflang="fr" data-title="Hydrazone" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a 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</div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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compounds - Hydrazones</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Hydrazone-2D.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydrazone-2D.png/150px-Hydrazone-2D.png" decoding="async" width="150" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydrazone-2D.png/225px-Hydrazone-2D.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydrazone-2D.png/300px-Hydrazone-2D.png 2x" data-file-width="1100" data-file-height="983" /></a><figcaption>Structure of the hydrazone functional group</figcaption></figure> <p><b>Hydrazones</b> are a class of <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> with the structure <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">R<sup class="template-chem2-sup">1</sup>R<sup class="template-chem2-sup">2</sup>C=N−NH<sub class="template-chem2-sub">2</sub></span>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> They are related to <a href="/wiki/Ketone" title="Ketone">ketones</a> and <a href="/wiki/Aldehyde" title="Aldehyde">aldehydes</a> by the replacement of the oxygen =O with the =<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N−NH<sub class="template-chem2-sub">2</sub></span> <a href="/wiki/Functional_group" title="Functional group">functional group</a>. They are formed usually by the action of <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a> on ketones or aldehydes.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-acetone_3-0" class="reference"><a href="#cite_note-acetone-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrazine, organohydrazines, and 1,1-diorganohydrazines react with aldehydes and ketones to give hydrazones. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Hydrazone_General_Synthesis.svg" class="mw-file-description" title="Hydrazone synthesis"><img alt="Hydrazone synthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Hydrazone_General_Synthesis.svg/300px-Hydrazone_General_Synthesis.svg.png" decoding="async" width="300" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Hydrazone_General_Synthesis.svg/450px-Hydrazone_General_Synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Hydrazone_General_Synthesis.svg/600px-Hydrazone_General_Synthesis.svg.png 2x" data-file-width="610" data-file-height="176" /></a></span></dd></dl> <p><a href="/wiki/Phenylhydrazine" title="Phenylhydrazine">Phenylhydrazine</a> reacts with <a href="/wiki/Reducing_sugar" title="Reducing sugar">reducing sugars</a> to form hydrazones known as <a href="/wiki/Osazone" title="Osazone">osazones</a>, which was developed by German chemist <a href="/wiki/Emil_Fischer" title="Emil Fischer">Emil Fischer</a> as a test to differentiate <a href="/wiki/Monosaccharide" title="Monosaccharide">monosaccharides</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrazones are the basis for various analyses of ketones and aldehydes. For example, <a href="/wiki/Dinitrophenylhydrazine" class="mw-redirect" title="Dinitrophenylhydrazine">dinitrophenylhydrazine</a> coated onto a <a href="/wiki/Silica" class="mw-redirect" title="Silica">silica</a> <a href="/wiki/Sorbent" title="Sorbent">sorbent</a> is the basis of an <a href="/wiki/Adsorption" title="Adsorption">adsorption</a> cartridge. The hydrazones are then eluted and analyzed by <a href="/wiki/High-performance_liquid_chromatography" title="High-performance liquid chromatography">high-performance liquid chromatography</a> (HPLC) using a <a href="/wiki/Ultraviolet" title="Ultraviolet">UV</a> detector. </p><p>The compound <a href="/wiki/Carbonyl_cyanide-p-trifluoromethoxyphenylhydrazone" title="Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone">carbonyl cyanide-<i>p</i>-trifluoromethoxyphenylhydrazone</a> (abbreviated as FCCP) is used to <a href="/wiki/Uncoupler" title="Uncoupler">uncouple</a> <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> synthesis and <a href="/wiki/Reduction_(chemistry)" class="mw-redirect" title="Reduction (chemistry)">reduction</a> of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in <a href="/wiki/Oxidative_phosphorylation" title="Oxidative phosphorylation">oxidative phosphorylation</a> in <a href="/wiki/Molecular_biology" title="Molecular biology">molecular biology</a>. </p><p>Hydrazones are the basis of <a href="/wiki/Bioconjugation" title="Bioconjugation">bioconjugation</a> strategies.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Hydrazone-based coupling methods are used in medical biotechnology to couple drugs to targeted antibodies (see <a href="/wiki/Antibody-drug_conjugate" class="mw-redirect" title="Antibody-drug conjugate">ADC</a>), e.g. antibodies against a certain type of cancer cell. The hydrazone-based bond is stable at neutral pH (in the blood), but is rapidly destroyed in the acidic environment of <a href="/wiki/Lysosome" title="Lysosome">lysosomes</a> of the cell. The drug is thereby released in the cell, where it exerts its function.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=3" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydrazones are susceptible to hydrolysis: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C=N−NR'<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O → R<sub class="template-chem2-sub">2</sub>C=O + H<sub class="template-chem2-sub">2</sub>N−NR'<sub class="template-chem2-sub">2</sub></span></dd></dl> <p><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> hydrazones are 10<sup>2</sup>- to 10<sup>3</sup>-fold more sensitive to hydrolysis than analogous <a href="/wiki/Oximes" class="mw-redirect" title="Oximes">oximes</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>When derived from hydrazine itself, hydrazones condense with a second <a href="/wiki/Equivalent_(chemistry)" title="Equivalent (chemistry)">equivalent</a> of a <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> to give <a href="/wiki/Azine" title="Azine">azines</a>:<sup id="cite_ref-OrgSynth_10-0" class="reference"><a href="#cite_note-OrgSynth-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C=N−NH<sub class="template-chem2-sub">2</sub> + R<sub class="template-chem2-sub">2</sub>C=O → R<sub class="template-chem2-sub">2</sub>C=N−N=CR<sub class="template-chem2-sub">2</sub> + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl> <p>Hydrazones are intermediates in the <a href="/wiki/Wolff%E2%80%93Kishner_reduction" title="Wolff–Kishner reduction">Wolff–Kishner reduction</a>. </p><p>Hydrazones are reactants in <a href="/wiki/Hydrazone_iodination" title="Hydrazone iodination">hydrazone iodination</a>, the <a href="/wiki/Shapiro_reaction" title="Shapiro reaction">Shapiro reaction</a>, and the <a href="/wiki/Bamford%E2%80%93Stevens_reaction" title="Bamford–Stevens reaction">Bamford–Stevens reaction</a> to <a href="/wiki/Vinyl_group" title="Vinyl group">vinyl</a> compounds. Hydrazones can also be synthesized by the <a href="/wiki/Japp%E2%80%93Klingemann_reaction" title="Japp–Klingemann reaction">Japp–Klingemann reaction</a> via <a href="/wiki/%CE%92-keto_acid" class="mw-redirect" title="Β-keto acid">β-keto acids</a> or β-keto-esters and aryl diazonium salts. Hydrazones are converted to <a href="/wiki/Azine" title="Azine">azines</a> when used in the preparation of 3,5-disubstituted 1<i>H</i>-<a href="/wiki/Pyrazole" title="Pyrazole">pyrazoles</a>,<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> a reaction also well known using <a href="/wiki/Hydrazine_hydrate" class="mw-redirect" title="Hydrazine hydrate">hydrazine hydrate</a>.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> With a <a href="/wiki/Transition_metal_catalyst" class="mw-redirect" title="Transition metal catalyst">transition metal catalyst</a>, hydrazones can serve as organometallic reagent surrogates to react with various electrophiles.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Lasri_condensation_reaction.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/700px-Lasri_condensation_reaction.svg.png" decoding="async" width="700" height="114" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/1050px-Lasri_condensation_reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Lasri_condensation_reaction.svg/1400px-Lasri_condensation_reaction.svg.png 2x" data-file-width="1685" data-file-height="275" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="N,N-dialkylhydrazones"><span id="N.2CN-dialkylhydrazones"></span><i>N</i>,<i>N</i>-dialkylhydrazones</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=4" title="Edit section: N,N-dialkylhydrazones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Enders_SAMP/RAMP_hydrazone_alkylation_reaction" class="mw-redirect" title="Enders SAMP/RAMP hydrazone alkylation reaction">Enders SAMP/RAMP hydrazone alkylation reaction</a></div> <p>In <i>N</i>,<i>N</i>-dialkylhydrazones<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> the C=N bond can be hydrolysed, oxidised and reduced, the N–N bond can be reduced to the free amine. The carbon atom of the C=N bond can react with organometallic nucleophiles. The alpha-hydrogen atom is more acidic by 10 <a href="/wiki/Order_of_magnitude" title="Order of magnitude">orders of magnitude</a> compared to the ketone and therefore more nucleophilic. Deprotonation with for instance <a href="/wiki/Lithium_diisopropylamide" title="Lithium diisopropylamide">lithium diisopropylamide</a> (LDA) gives an <b>azaenolate</b> which can be alkylated by alkyl halides.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The hydrazines SAMP and RAMP function as <a href="/wiki/Chiral_auxiliary" title="Chiral auxiliary">chiral auxiliary</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:SAMP_RAMP_Struktur.svg" class="mw-file-description" title="SAMP RAMP chiral auxiliaries"><img alt="SAMP RAMP chiral auxiliaries" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/SAMP_RAMP_Struktur.svg/300px-SAMP_RAMP_Struktur.svg.png" decoding="async" width="300" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/SAMP_RAMP_Struktur.svg/450px-SAMP_RAMP_Struktur.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/SAMP_RAMP_Struktur.svg/600px-SAMP_RAMP_Struktur.svg.png 2x" data-file-width="532" data-file-height="195" /></a></span></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Recovery_of_carbonyl_compounds_from_N,N-dialkylhydrazones"><span id="Recovery_of_carbonyl_compounds_from_N.2CN-dialkylhydrazones"></span>Recovery of carbonyl compounds from N,N-dialkylhydrazones</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=5" title="Edit section: Recovery of carbonyl compounds from N,N-dialkylhydrazones"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several methods are known to recover carbonyl compounds from N,N-dialkylhydrazones.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Procedures include oxidative, hydrolytic or reductive cleavage conditions and can be compatible with a wide range of functional groups. </p> <div class="mw-heading mw-heading2"><h2 id="Gallery">Gallery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=6" title="Edit section: Gallery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional" style="max-width: 815px;"> <li class="gallerycaption">Hydrazones</li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Benzophenone_hydrazone-structure.png" class="mw-file-description" title="Benzophenone hydrazone, an illustrative hydrazone"><img alt="Benzophenone hydrazone, an illustrative hydrazone" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Benzophenone_hydrazone-structure.png/120px-Benzophenone_hydrazone-structure.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/75/Benzophenone_hydrazone-structure.png/180px-Benzophenone_hydrazone-structure.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/75/Benzophenone_hydrazone-structure.png/240px-Benzophenone_hydrazone-structure.png 2x" data-file-width="1765" data-file-height="1263" /></a></span></div> <div class="gallerytext">Benzophenone hydrazone, an illustrative hydrazone</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg" class="mw-file-description" title="Carbonyl cyanide m-chlorophenyl hydrazone"><img alt="Carbonyl cyanide m-chlorophenyl hydrazone" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg/120px-Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg.png" decoding="async" width="120" height="73" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg/180px-Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ab/Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg/240px-Carbonyl_cyanide_m-chlorophenyl_hydrazone.svg.png 2x" data-file-width="1286" data-file-height="780" /></a></span></div> <div class="gallerytext"><a href="/wiki/Carbonyl_cyanide_m-chlorophenyl_hydrazone" title="Carbonyl cyanide m-chlorophenyl hydrazone">Carbonyl cyanide <i>m</i>-chlorophenyl hydrazone</a></div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Gyromitrin.svg" class="mw-file-description" title="Gyromitrin (acetaldehyde methylformylhydrazone), a toxin"><img alt="Gyromitrin (acetaldehyde methylformylhydrazone), a toxin" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/Gyromitrin.svg/120px-Gyromitrin.svg.png" decoding="async" width="120" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/Gyromitrin.svg/180px-Gyromitrin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/39/Gyromitrin.svg/240px-Gyromitrin.svg.png 2x" data-file-width="512" data-file-height="389" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Gyromitrin" title="Gyromitrin">Gyromitrin</a> (acetaldehyde methylformylhydrazone), a toxin</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Dihydralazine_structure.svg" class="mw-file-description" title="Dihydralazine, an antihypertensive drug"><img alt="Dihydralazine, an antihypertensive drug" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Dihydralazine_structure.svg/93px-Dihydralazine_structure.svg.png" decoding="async" width="93" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Dihydralazine_structure.svg/140px-Dihydralazine_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9e/Dihydralazine_structure.svg/186px-Dihydralazine_structure.svg.png 2x" data-file-width="494" data-file-height="636" /></a></span></div> <div class="gallerytext"> <a href="/wiki/Dihydralazine" title="Dihydralazine">Dihydralazine</a>, an antihypertensive drug</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:NERYOZ.png" class="mw-file-description" title="X-ray structure of DNP-derived hydrazone of benzophenone. Selected parameters: C=N, 128 pm; N-N, 138 pm, N-N-C(Ar), 119 pm[20]"><img alt="X-ray structure of DNP-derived hydrazone of benzophenone. Selected parameters: C=N, 128 pm; N-N, 138 pm, N-N-C(Ar), 119 pm[20]" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/NERYOZ.png/120px-NERYOZ.png" decoding="async" width="120" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/39/NERYOZ.png/180px-NERYOZ.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/39/NERYOZ.png/240px-NERYOZ.png 2x" data-file-width="1200" data-file-height="921" /></a></span></div> <div class="gallerytext">X-ray structure of DNP-derived hydrazone of <a href="/wiki/Benzophenone" title="Benzophenone">benzophenone</a>. Selected parameters: C=N, 128 pm; N-N, 138 pm, N-N-C(Ar), 119 pm<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=7" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Azo_compound" title="Azo compound">Azo compound</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Nitrosamine" title="Nitrosamine">Nitrosamine</a></li> <li><a href="/wiki/Hydrogenation_of_carbon%E2%80%93nitrogen_double_bonds" title="Hydrogenation of carbon–nitrogen double bonds">Hydrogenation of carbon–nitrogen double bonds</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Hydrazone&action=edit&section=8" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output 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.cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMarch,_Jerry1985" class="citation cs2"><a href="/wiki/Jerry_March" title="Jerry March">March, Jerry</a> (1985), <a rel="nofollow" class="external text" href="https://www.google.co.in/books/edition/_/ZKqWAQAACAAJ?hl=en"><i>Advanced Organic Chemistry: Reactions, 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aria-labelledby="Functional_groups" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Functional_groups" title="Template:Functional groups"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Functional_groups" title="Template talk:Functional groups"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Functional_groups" title="Special:EditPage/Template:Functional groups"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Functional_groups" style="font-size:114%;margin:0 4em"><a href="/wiki/Functional_group" title="Functional group">Functional groups</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrocarbon" title="Hydrocarbon">Hydrocarbons</a> <br /><span class="nobold">(only C and H)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alkyl" class="mw-redirect" title="Alkyl">Alkyl</a> <ul><li><a href="/wiki/Methyl_group" title="Methyl group">Methyl</a></li> <li><a href="/wiki/Ethyl_group" title="Ethyl group">Ethyl</a></li> <li><a href="/wiki/Propyl_group" title="Propyl group">Propyl</a></li> <li><a href="/wiki/Cyclopropyl" class="mw-redirect" title="Cyclopropyl">Cyclopropyl</a></li> <li><a href="/wiki/Butyl_group" title="Butyl group">Butyl</a></li> <li><a href="/wiki/Pentyl_group" title="Pentyl group">Pentyl</a></li></ul></li> <li><a href="/wiki/Methylene_group" title="Methylene group">Methylene</a> <ul><li><a href="/wiki/Methylene_bridge" title="Methylene bridge">Bridge</a></li> <li><a href="/wiki/Methine_group" title="Methine group">Methine</a></li></ul></li> <li><a href="/wiki/Alkene" title="Alkene">Alkene</a> <ul><li><a href="/wiki/Vinyl_group" title="Vinyl group">Vinyl</a></li> <li><a href="/wiki/Allyl_group" title="Allyl group">Allyl</a></li> <li><a href="/wiki/Propenyl" title="Propenyl">1-Propenyl</a></li> <li><a href="/wiki/Crotyl_group" title="Crotyl group">Crotyl</a></li> <li><a href="/wiki/Allenes" title="Allenes">Allene</a></li> <li><a href="/wiki/Cumulene" title="Cumulene">Cumulene</a></li></ul></li> <li><a href="/wiki/Aryl" class="mw-redirect" title="Aryl">Aryl</a> <ul><li><a href="/wiki/Phenyl_group" title="Phenyl group">Phenyl</a></li> <li><a href="/wiki/Benzyl_group" title="Benzyl group">Benzyl</a></li></ul></li> <li><a href="/wiki/Alkyne" title="Alkyne">Alkyne</a></li> <li><a href="/wiki/Carbene" title="Carbene">Carbene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only <a href="/wiki/Carbon" title="Carbon">carbon</a>, <br /><a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>, <br />and <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> <br /><span class="nobold">(only C, H and O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">R-O-R</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetal" title="Acetal">Acetal</a></li> <li><a href="/wiki/Alcohol_(chemistry)" title="Alcohol (chemistry)">Alcohol</a></li> <li><a href="/wiki/Alkoxy_group" title="Alkoxy group">Alkoxy</a> <ul><li><a href="/wiki/Methoxy_group" title="Methoxy group">Methoxy</a></li></ul></li> <li><a href="/wiki/Ether" title="Ether">Ether</a> <ul><li><a href="/wiki/Enol_ether" title="Enol ether">Enol ether</a></li> <li><a href="/wiki/Epoxide" title="Epoxide">Epoxide</a></li></ul></li> <li><a href="/wiki/Organic_peroxides" title="Organic peroxides">Peroxy</a> <ul><li><a href="/wiki/Hydroperoxide" title="Hydroperoxide">Hydroperoxy</a></li> <li><a href="/wiki/Dioxirane" title="Dioxirane">Dioxiranes</a></li></ul></li> <li><a href="/wiki/Ethylenedioxy" title="Ethylenedioxy">Ethylenedioxy</a></li> <li><a href="/wiki/Methylenedioxy" title="Methylenedioxy">Methylenedioxy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonyl_group" title="Carbonyl group">carbonyl</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acyl_group" title="Acyl group">Acyl</a> <ul><li><a href="/wiki/Acetyl_group" title="Acetyl group">Acetyl</a></li> <li><a href="/wiki/Acryloyl_group" class="mw-redirect" title="Acryloyl group">Acryloyl</a></li> <li><a href="/wiki/Benzoyl_group" title="Benzoyl group">Benzoyl</a></li></ul></li> <li><a href="/wiki/Aldehyde" title="Aldehyde">Aldehyde</a> <ul><li><a href="/wiki/Ketene" title="Ketene">Ketene</a></li></ul></li> <li><a href="/wiki/Ketone" title="Ketone">Ketone</a></li> <li><a href="/wiki/Ynone" title="Ynone">Ynone</a></li> <li><a href="/wiki/Reductone" title="Reductone">Reductone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">carboxy</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboxylic_acid" title="Carboxylic acid">Carboxyl</a> <ul><li><a href="/wiki/Acetoxy_group" title="Acetoxy group">Acetoxy</a></li> <li><a href="/wiki/Carboxylic_anhydride" class="mw-redirect" title="Carboxylic anhydride">Anhydride</a></li></ul></li> <li><a href="/wiki/Ester" title="Ester">Ester</a> <ul><li><a href="/wiki/Orthoester" class="mw-redirect" title="Orthoester">Orthoester</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Only one <br />element, <br />not being <br />carbon, <br />hydrogen, <br />or oxygen <br /><span class="nobold">(one element, <br />not C, H or O)</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amine" title="Amine">Amine</a> <ul><li><a href="/wiki/Enamine" title="Enamine">Enamine</a></li> <li><a href="/wiki/Quaternary_ammonium_cation" title="Quaternary ammonium cation">Ammonium</a></li></ul></li> <li><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazo</a></li> <li><a href="/wiki/Nitrene" title="Nitrene">Nitrene</a></li> <li><a href="/wiki/Imine" title="Imine">Imine</a></li> <li><a href="/wiki/Oxime" title="Oxime">Oxime</a></li> <li><a class="mw-selflink selflink">Hydrazone</a></li> <li><a href="/wiki/Azo_compound" title="Azo compound">Azo</a></li> <li><a href="/wiki/Amide_(functional_group)" title="Amide (functional group)">Amide</a></li> <li><a href="/wiki/Imidate" class="mw-redirect" title="Imidate">Imidate</a></li> <li><a href="/wiki/Amidine" title="Amidine">Amidine</a></li> <li><a href="/wiki/Carbamate" title="Carbamate">Carbamate</a></li> <li><a href="/wiki/Imide" title="Imide">Imide</a></li> <li><a href="/wiki/Nitrile" title="Nitrile">Nitrile</a></li> <li><a href="/wiki/Isocyanide" title="Isocyanide">Isonitrile</a></li> <li><a href="/wiki/Cyanate_ester" title="Cyanate ester">Cyanate</a></li> <li><a href="/wiki/Isocyanate" title="Isocyanate">Isocyanate</a></li> <li><a href="/wiki/Nitrate_ester" title="Nitrate ester">Nitrate</a></li> <li><a href="/wiki/Nitrite_ester" class="mw-redirect" title="Nitrite ester">Nitrite</a></li> <li><a href="/wiki/Nitro_compound" title="Nitro compound">Nitro</a></li> <li><a href="/wiki/Nitroso" title="Nitroso">Nitroso</a></li> <li><a href="/wiki/NONOate" title="NONOate">NONOate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Organophosphate" title="Organophosphate">Phosphate</a> <ul><li><a href="/wiki/Phosphodiester" class="mw-redirect" title="Phosphodiester">Phosphodiester</a></li></ul></li> <li><a href="/wiki/Phosphonate" title="Phosphonate">Phosphonate</a> <ul><li><a href="/wiki/Phosphite_ester" title="Phosphite ester">Phosphite</a></li></ul></li> <li><a href="/wiki/Phosphonite" title="Phosphonite">Phosphonous</a></li> <li><a href="/wiki/Phosphinate" title="Phosphinate">Phosphinate</a></li> <li><a href="/wiki/Phosphine_oxide" title="Phosphine oxide">Phosphine oxide</a></li> <li><a href="/wiki/Organophosphine" title="Organophosphine">Phosphine</a> <ul><li><a href="/wiki/Phosphonium" title="Phosphonium">Phosphonium</a></li></ul></li> <li><a href="/wiki/Phosphaalkene" title="Phosphaalkene">Phosphaalkene</a></li> <li><a href="/wiki/Phosphaalkyne" title="Phosphaalkyne">Phosphaalkyne</a></li> <li><a href="/wiki/1-Phosphaallenes" title="1-Phosphaallenes">Phosphaallene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiol" title="Thiol">Thiol</a></li> <li><a href="/wiki/Sulfide_(organic)" class="mw-redirect" title="Sulfide (organic)">Sulfide</a> <ul><li><a href="/wiki/Sulfonium" title="Sulfonium">Sulfonium</a></li></ul></li> <li><a href="/wiki/Persulfide" title="Persulfide">Persulfide</a></li> <li><a href="/wiki/Disulfide" title="Disulfide">Disulfide</a></li> <li><a href="/wiki/Sulfenic_acid" title="Sulfenic acid">Sulfenic acid</a></li> <li><a href="/wiki/Thiosulfinate" title="Thiosulfinate">Thiosulfinate</a></li> <li><a href="/wiki/Sulfoxide" title="Sulfoxide">Sulfoxide</a></li> <li><a href="/wiki/Thiosulfonate" title="Thiosulfonate">Thiosulfonate</a></li> <li><a href="/wiki/Sulfinic_acid" title="Sulfinic acid">Sulfinic acid</a></li> <li><a href="/wiki/Sulfone" title="Sulfone">Sulfone</a></li> <li><a href="/wiki/Sulfonic_acid" title="Sulfonic acid">Sulfonic acid</a></li> <li><a href="/wiki/Thioketone" title="Thioketone">Thioketone</a></li> <li><a href="/wiki/Thial" title="Thial">Thial</a></li> <li><a href="/wiki/Thioester" title="Thioester">Thioester</a></li> <li><a href="/wiki/Thionoester" class="mw-redirect" title="Thionoester">Thionoester</a></li> <li><a href="/wiki/Thioxanthate" title="Thioxanthate">Thioxanthate</a></li> <li><a href="/wiki/Xanthate" title="Xanthate">Xanthate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Boron" title="Boron">Boron</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Boronic_acid" title="Boronic acid">Boronic acid</a></li> <li><a href="/wiki/Borinic_acid" title="Borinic acid">Borinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selenium" title="Selenium">Selenium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Selenol" title="Selenol">Selenol</a></li> <li><a href="/wiki/Selenonic_acid" title="Selenonic acid">Selenonic acid</a></li> <li><a href="/wiki/Seleninic_acid" title="Seleninic acid">Seleninic acid</a></li> <li><a href="/wiki/Selenenic_acid" title="Selenenic acid">Selenenic acid</a></li> <li><a href="/wiki/Selone" title="Selone">Selone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tellurium" title="Tellurium">Tellurium</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tellurol" title="Tellurol">Tellurol</a></li> <li><a href="/wiki/Telluroketone" title="Telluroketone">Telluroketone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i><a href="/wiki/Halocarbon" title="Halocarbon">Halo</a></i></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Haloalkane" title="Haloalkane">Haloalkane</a> <ul><li><a href="/wiki/Fluoroethyl" title="Fluoroethyl">Fluoroethyl</a></li> <li><a href="/wiki/Trifluoromethyl" class="mw-redirect" title="Trifluoromethyl">Trifluoromethyl</a></li> <li><a href="/wiki/Trichloromethyl_group" title="Trichloromethyl group">Trichloromethyl</a></li> <li><a href="/wiki/Trifluoromethoxy_group" title="Trifluoromethoxy group">Trifluoromethoxy</a></li> <li><a href="/wiki/Iodane" class="mw-redirect" title="Iodane">Hypervalent iodine</a></li></ul></li> <li><a href="/wiki/Vinyl_halide" title="Vinyl halide">Vinyl halide</a> <ul><li><a href="/wiki/Vinyl_iodide_functional_group" title="Vinyl iodide functional group">Iodide</a></li></ul></li> <li><a href="/wiki/Acyl_halide" title="Acyl halide">Acyl halide</a> <ul><li><a href="/wiki/Acyl_chloride" title="Acyl chloride">Chloride</a></li></ul></li> <li><a href="/wiki/Perchlorate_ester" class="mw-redirect" title="Perchlorate ester">Perchlorate</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">Isothiocyanate</a></li> <li><a href="/wiki/Phosphoramides" title="Phosphoramides">Phosphoramides</a></li> <li><a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">Sulfenyl chloride</a></li> <li><a href="/wiki/Sulfonamide" title="Sulfonamide">Sulfonamide</a></li> <li><a href="/wiki/Organic_thiocyanates" title="Organic thiocyanates">Thiocyanate</a></li> <li><a href="/wiki/Sulfinylamine" title="Sulfinylamine">Sulfinylamines</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt><span class="nobold">See also</span></dt> <dd><i><a href="/wiki/Chemical_classification" class="mw-redirect" title="Chemical classification">chemical classification</a></i></dd> <dd><i><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">chemical nomenclature</a></i> <dl><dd><a href="/wiki/IUPAC_nomenclature_of_inorganic_chemistry" title="IUPAC nomenclature of inorganic chemistry">inorganic</a></dd> <dd><a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">organic</a></dd></dl></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Hydrazines" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrazines" title="Template:Hydrazines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrazines" title="Template talk:Hydrazines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrazines" title="Special:EditPage/Template:Hydrazines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrazines" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazines</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Phenylthiosemicarbazide" title="4-Phenylthiosemicarbazide">4-PTSC</a></li> <li><a href="/wiki/Acylhydrazine" class="mw-redirect" title="Acylhydrazine">Acylhydrazine</a></li> <li><a href="/wiki/Adipic_acid_dihydrazide" title="Adipic acid dihydrazide">ADH</a></li> <li><a href="/wiki/Adjudin" title="Adjudin">Adjudin</a></li> <li><a href="/wiki/Agaritine" title="Agaritine">Agaritine</a></li> <li><a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Cadralazine" title="Cadralazine">Cadralazine</a></li> <li><a href="/wiki/Carbazide" title="Carbazide">Carbazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Carbohydrazide" title="Carbohydrazide">Carbohydrazide</a></li> <li><a href="/wiki/Daminozide" title="Daminozide">Daminozide</a></li> <li><a href="/wiki/Dihydralazine" title="Dihydralazine">Dihydralazine</a></li> <li><a href="/wiki/2,4-Dinitrophenylhydrazine" title="2,4-Dinitrophenylhydrazine">DNPH</a></li> <li><a href="/wiki/Endralazine" title="Endralazine">Endralazine</a></li> <li><a href="/wiki/Gyromitrin" title="Gyromitrin">Gyromitrin</a></li> <li><a href="/wiki/HBT_(explosive)" title="HBT (explosive)">HBT</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Hydrazide" title="Hydrazide">Hydrazide</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazine</a></li> <li><a class="mw-selflink selflink">Hydrazone</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Monomethylhydrazine" title="Monomethylhydrazine">MMH</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Phenylethylidenehydrazine" title="Phenylethylidenehydrazine">PEH</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Phenylhydrazine" title="Phenylhydrazine">Phenylhydrazine</a></li> <li><a href="/wiki/Pildralazine" title="Pildralazine">Pildralazine</a></li> <li><a href="/wiki/Pimagedine" title="Pimagedine">Pimagedine</a></li> <li><a href="/wiki/Pivalylbenzhydrazine" class="mw-redirect" title="Pivalylbenzhydrazine">Pivalylbenzhydrazine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Safrazine" title="Safrazine">Safrazine</a></li> <li><a href="/wiki/Semicarbazide" title="Semicarbazide">Semicarbazide</a></li> <li><a href="/wiki/Semicarbazone" title="Semicarbazone">Semicarbazone</a></li> <li><a href="/wiki/1,2-Dimethylhydrazine" class="mw-redirect" title="1,2-Dimethylhydrazine">SDMH</a></li> <li><a href="/wiki/Tetrafluorohydrazine" title="Tetrafluorohydrazine">Tetrafluorohydrazine</a></li> <li><a href="/wiki/Unsymmetrical_dimethylhydrazine" title="Unsymmetrical dimethylhydrazine">UDMH</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" 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