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	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443693360		| verifiedrevid = 450765459
⚫	| ImageFile = Dimethylglyoxime.png
	| ImageName = Dimethylglyoxime		| ImageFile = Dimethylglyoxime.svg
			| ImageFile1 = Dimethylglyoxime-3D-balls.png
	| IUPACName = 2,3-Butanedione Dioxime
		⚫	| ImageName = Dimethylglyoxime
⚫	| OtherNames = Dimethylglyoxime,<br />Diacetyl dioxime,<br />Chugaev's Reagent<br />2,3-diisonitrosobutane
			| IUPACName = ''N'',''{{prime|N}}''-Dihydroxy-2,3-butanediimine
⚫	| Section1 = {{Chembox Identifiers
		⚫	| OtherNames = {{bulletedlist|Dimethylglyoxime|Diacetyl dioxime|Butane-2,3-dioxime|Chugaev's reagent}}
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	|Section1={{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 10606175		| ChemSpiderID = 10606175
	| InChI = 1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+		| InChI = 1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+
⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| UNII = 2971MFT1KY
	| SMILES = C\C(=N\O)\C(\C)=N\O		| SMILES = C\C(=N\O)\C(\C)=N\O
	| InChIKey = JGUQDUKBUKFFRO-CIIODKQPBA		| InChIKey = JGUQDUKBUKFFRO-CIIODKQPBA
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	| StdInChIKey = JGUQDUKBUKFFRO-CIIODKQPSA-N		| StdInChIKey = JGUQDUKBUKFFRO-CIIODKQPSA-N
	| CASNo = 95-45-4		| CASNo = 95-45-4
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| RTECS = EK2975000		| CASNo2 = 17117-97-4
			| CASNo2_Ref = {{cascite|correct|CAS}}
			| CASNo2_Comment = (''E'')
			| RTECS = EK2975000
			| PubChem = 135399895
			| EC_number = 202-420-1
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
		⚫	| UNII = 2971MFT1KY
			| ChEMBL = 3184098
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C = 4		| C = 4
	| H = 8		| H = 8
	| N = 2		| N = 2
	| O = 2		| O = 2
	| Appearance = White/Off White Powder		| Appearance = White/Off White Powder
	| Density = 1.37 g/cm<sup>3</sup>		| Density = 1.37 g/cm<sup>3</sup>
	| Solubility = low		| Solubility = low
	| MeltingPtCL = 240		| MeltingPtC = 240 to 241
		⚫	| BoilingPt = decomposes
	| MeltingPtCH = 241
⚫	| BoilingPt = decomp.
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| Dipole = 0		| Dipole = 0
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| MainHazards = Toxic, Skin/Eye Irritant		| MainHazards = Toxic, Skin/Eye Irritant
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| RPhrases = {{R20/22}}		| GHSPictograms = {{GHS02}}{{GHS06}}
			| GHSSignalWord = Danger
	| SPhrases = {{R22}}, {{R36/37}}
			| HPhrases = {{H-phrases|228|301}}
⚫	}}| Section8 = {{Chembox Related
			| PPhrases = {{P-phrases|210|240|241|264|270|280|301+310|321|330|370+378|405|501}}
⚫	| OtherCpds = ]<br />]
			}}
		⚫	|Section8={{Chembox Related
		⚫	| OtherCompounds = ]<br />]
	}}		}}
	}}		}}
⚫	'''Dimethylglyoxime''' is a ] described by the formula CH<sub>3</sub>C(NOH)C(NOH)CH<sub>3</sub>. This colourless solid is the di] derivative of the diketone ] (also known as 2,3-butanedione). DmgH<sub>2</sub> is used in the analysis of ] or ]. Its ]es are of theoretical interest as models for enzymes and as catalysts. Many related ligands can be prepared from other diketones, e.g. ].
		⚫	'''Dimethylglyoxime''' is a ] described by the formula CH<sub>3</sub>C(NOH)C(NOH)CH<sub>3</sub>. Its abbreviation is '''dmgH<sub>2</sub>''' for neutral form, and '''dmgH<sup>−</sup>''' for anionic form, where H stands for hydrogen. This colourless solid is the di] derivative of the di] butane-2,3-dione (also known as ]). DmgH<sub>2</sub> is used in the analysis of ] or ]. Its ]es are of theoretical interest as models for enzymes and as catalysts. Many related ] can be prepared from other diketones, e.g. ].
⚫	==Preparation==
⚫	Dimethylglyoxime can be prepared from ] first by reaction with ] followed b ] monosulfonate:<ref>{{OrgSynth | author = Semon, W. L.; Damerell, V. R. | title = Dimethylglyoxime | collvol = 2 | collvolpages = 204 | year = 1943 | prep = cv2p0204}}</ref>
		⚫	==Preparation and reactions==
⚫	:]
		⚫	Dimethylglyoxime can be prepared from ] first by reaction with ] to give ]. The second ] is installed using sodium ] monosulfonate:<ref>{{OrgSynth | author = Semon, W. L. | author2 = Damerell, V. R. | title = Dimethylglyoxime | volume = 10 | pages = 22 | year = 1930 | doi = 10.15227/orgsyn.010.0022}}</ref>
		⚫	]
	==Ni(dmgH)<sub>2</sub>==
	]
	]
	Dimethylglyoxime is used as a ] in the ] of nickel. The use of DMG as a reagent to detect ] was discovered by ] in 1905.<ref>{{cite journal
	| title = Über ein neues, empfindliches Reagens auf Nickel
	| author = Lev Tschugaeff
	| journal = Berichte der deutschen chemischen Gesellschaft
	| volume = 38
	| issue = 3
	| pages = 2520–2522
	| year = 1905
	| url =
	| doi = 10.1002/cber.19050380317 }}</ref> For ], dmgH<sub>2</sub> is often used as a solution in ]. It is the ], not dmgH<sub>2</sub> itself, that forms the complexes. Furthermore, a pair of dmgH<sup>-</sup> ligands are joined through hydrogen bonds to give a ]. The most famous complex is the bright red Ni(dmgH)<sub>2</sub>, formed by treatment of Ni(II) sources with dmgH<sub>2</sub>. This planar complex is very poorly soluble and so ] from solution. This method is used for the gravimetric determination of nickel, e.g. in ores.
	<br clear="left" /><!-- stop image from extending into next section -->
			] is produced by reduction of dimethylglyoxime with ].<ref>{{cite journal |doi=10.1021/ic50203a022 |title=Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III) |date=1980 |last1=Hilleary |first1=Christopher J. |last2=Them |first2=Theodore F. |last3=Tapscott |first3=Robert E. |journal=Inorganic Chemistry |volume=19 |pages=102–107 }}</ref>
	==Cobaloximes==
	The nitrogen atoms in dmgH<sub>2</sub> and its complexes are sp<sup>2</sup> hybridized.<ref>{{cite book | author = Girolami, G.. S.; Rauchfuss, T.B.; Angelici, R. J.| title = Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual | edition = 3rd | date = 1999 | pages = 213–215 }}</ref> Because of the planarity of the resulting ligand, the macrocycle <sub>2</sub><sup>2-</sup> resembles some biologically important macrocyclic ligands, as found for example in vitamin B12 and myoglobin. A well known family of model complexes, the cobaloximes, have the formula CoR(dmgH)<sub>2</sub>L, where R is an ] group and L is typically pyridine. In such complexes, L and R occupy “axial” positions on the cobalt, perpendicular to the plane of the (dmgH)<sub>2</sub>.
			==Complexes==
			Dimethylglyoxime forms complexes with metals including ],<ref>{{Cite journal |author=Lev Tschugaeff |year=1905 |title=Über ein neues, empfindliches Reagens auf Nickel |trans-title=About a new, sensitive reagent on nickel |url=https://zenodo.org/record/1426158 |journal=Berichte der Deutschen Chemischen Gesellschaft |language=de |volume=38 |issue=3 |pages=2520–2522 |doi=10.1002/cber.19050380317}}</ref> ] and ].<ref>{{cite book |author1=Girolami, G. S. |url=https://archive.org/details/synthesistechniq0000giro/page/213 |title=Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual |author2=Rauchfuss, T.B. |author3=Angelici, R. J. |date=1999 |isbn=0-935702-48-2 |edition=3rd |pages=213–215 |via=Internet Archive}}</ref> These complexes are used to separate those cations from solutions of metal salts and in ]. It is also used in ] to precipitate ] from solutions of ].
			{{Gallery
			| title = Dimethylglyoxime Complexes
			| align = center
			| height = 200px
			| width = 100%
			|File:Ni-DADO.svg|Reaction of ]
			|File:Nickel Dimethylglyoxime 2014.05.08.jpg|Sample of ]
			|File:Structure of Chloro(pyridine)cobaloxime fixed.png|Structure of chloro(pyridine)cobaloxime
			}}
	==References==		==References==
	{{reflist}}		{{Reflist}}
			{{Authority control}}
⚫	]
⚫	]
		⚫	]
	]
		⚫	]
	]
	]
	]
	]
	]
	]
	]