Dimethylglyoxime

Dimethylglyoxime
Names
	IUPAC name N,N′-Dihydroxy-2,3-butanediimine
	Other names Dimethylglyoxime; Diacetyl dioxime; Butane-2,3-dioxime; Chugaev's reagent;
Identifiers
CAS Number	95-45-4 ; 17117-97-4 (E) ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3184098;
ChemSpider	10606175 ;
ECHA InfoCard	100.002.201
EC Number	202-420-1;
PubChem CID	135399895;
RTECS number	EK2975000;
UNII	2971MFT1KY ;
CompTox Dashboard (EPA)	DTXSID2044393 ;
	InChI InChI=1S/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+ Key: JGUQDUKBUKFFRO-CIIODKQPSA-N ; InChI=1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+ Key: JGUQDUKBUKFFRO-CIIODKQPBA;
	SMILES C\C(=N\O)\C(\C)=N\O;
Properties
Chemical formula	C4H8N2O2
Molar mass	116.120 g·mol−1
Appearance	White/Off White Powder
Density	1.37 g/cm3
Melting point	240 to 241 °C (464 to 466 °F; 513 to 514 K)
Boiling point	decomposes
Solubility in water	low
Structure
Dipole moment	0
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic, Skin/Eye Irritant
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H301
Precautionary statements	P210, P240, P241, P264, P270, P280, P301+P310, P321, P330, P370+P378, P405, P501
NFPA 704 (fire diamond)	2
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	Hydroxylamine; salicylaldoxime
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dimethylglyoxime is a chemical compound described by the formula CH₃C(NOH)C(NOH)CH₃. Its abbreviation is dmgH₂ for neutral form, and dmgH⁻ for anionic form, where H stands for hydrogen. This colourless solid is the dioxime derivative of the diketone butane-2,3-dione (also known as diacetyl). DmgH₂ is used in the analysis of palladium or nickel. Its coordination complexes are of theoretical interest as models for enzymes and as catalysts. Many related ligands can be prepared from other diketones, e.g. benzil.

Preparation and reactions

Dimethylglyoxime can be prepared from butanone first by reaction with ethyl nitrite to give biacetyl monoxime. The second oxime is installed using sodium hydroxylamine monosulfonate:^[1]

2,3-Butanediamine is produced by reduction of dimethylglyoxime with lithium aluminium hydride.^[2]

Complexes

Dimethylglyoxime forms complexes with metals including nickel,^[3] palladium and cobalt.^[4] These complexes are used to separate those cations from solutions of metal salts and in gravimetric analysis. It is also used in precious metals refining to precipitate palladium from solutions of palladium chloride.

Dimethylglyoxime Complexes

Reaction of Ni-dmg-Formation
Sample of Ni(dmgH)₂
Structure of chloro(pyridine)cobaloxime

References

^ Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.
^ Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry. 19: 102–107. doi:10.1021/ic50203a022.
^ Lev Tschugaeff (1905). "Über ein neues, empfindliches Reagens auf Nickel" [About a new, sensitive reagent on nickel]. Berichte der Deutschen Chemischen Gesellschaft (in German). 38 (3): 2520–2522. doi:10.1002/cber.19050380317.
^ Girolami, G. S.; Rauchfuss, T.B.; Angelici, R. J. (1999). Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual (3rd ed.). pp. 213–215. ISBN 0-935702-48-2 – via Internet Archive.

[1] Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.

[2] Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry. 19: 102–107. doi:10.1021/ic50203a022.

[3] Lev Tschugaeff (1905). "Über ein neues, empfindliches Reagens auf Nickel" [About a new, sensitive reagent on nickel]. Berichte der Deutschen Chemischen Gesellschaft (in German). 38 (3): 2520–2522. doi:10.1002/cber.19050380317.

[4] Girolami, G. S.; Rauchfuss, T.B.; Angelici, R. J. (1999). Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual (3rd ed.). pp. 213–215. ISBN 0-935702-48-2 – via Internet Archive.

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