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Dimethylglyoxime
Names
IUPAC name
Other names Dimethylglyoxime Diacetyl dioxime Butane-2,3-dioxime Chugaev's reagent
Identifiers
95-45-4
ChEMBL
ChemSpider	10606175
ECHA InfoCard	100.002.201
EC Number
PubChemCID
RTECS number	EK2975000
UNII
CompTox Dashboard(EPA)
InChI=1S/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+
CC(=NO)C(C)=NO
Properties
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
low
Structure
0
Hazards
Main hazards	Toxic, Skin/Eye Irritant
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Danger
H228, H301
P210, P240, P241, P264, P270, P280, P301+310, P321, P330, P370+378, P405, P501
NFPA 704 (fire diamond)
Related compounds
Hydroxylamine salicylaldoxime
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

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Preparation[edit]

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]

Complexes[edit]

Dimethylglyoxime is used to detect and quantify nickel, which forms the bright red complex nickel bis(dimethylglyoximate) (Ni(dmgH)₂). The reaction was discovered by L. A. Chugaev in 1905.^[2]

Cobalt complexes have also received much attention. In chloro(pyridine)cobaloxime^[3] the macrocycle [dmgH]₂²⁻ mimics the macrocyclic ligand found in vitamin B12.

Structure of chloro(pyridine)cobaloxime.

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References[edit]

^Semon, W. L.; Damerell, V. R. (1930). 'Dimethylglyoxime'. Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.CS1 maint: multiple names: authors list (link)
^Lev Tschugaeff (1905). 'Über ein neues, empfindliches Reagens auf Nickel'. Berichte der Deutschen Chemischen Gesellschaft. 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.