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.

Preparation[edit]

Oct 07, 2009 Hello, I would really appreciate some help. I had to do a gravimetric analysis of Nickel in Ore. My question is, how can I determine the percent by mass of the Nickel having only the mass of the Nickel complex (Ni(DMGH2) and the ore mass? I don't know how to find the mass of only the Nickel from the Nickel complex. If anyone knows, please help!!! To achieve EAN of 36, $$Ni(DMG)2$$, needs two electrons. However there are few exceptions from EAN rule. Hence, $$Ni(DMG)2$$ does not act as oxidizing agent. Thus option A is incorrect. 2 Dimethylglyoxime + Ni 2+- Ni(DMG) 2 + 2 H + The Ni(DMG) 2 complex (MW 288.9 g/mole) is stable to heat and is unusually hydrophobic; it will dry quickly in an oven at 110-120 o C to yield a pure substance whose weight can be used to calculate the nickel content of the original sample. Ni(dmg) 2 2+ complex (Figure 1d) Dimethylgloxine (dmg) is a bidentate ligand that chelates a large number of metals. Only two dmg molecules are required per metal center because Ni(dmg) 2 2+ has a square-planar geometry. Add 1% dmg to the aqueous complex. A solid pink/red precipitate forms, the insoluble Ni(dmg) 2 2+ complex.

Ni(dmgH) 2 complex can serve as active sites to promote H 2 generation of MOFs. The efficient charge transfer from MOF to Ni(dmgH) 2 causes the enhanced H 2 production. The low cost and easy operation makes Ni(dmgH) 2 having great potential for photocatalytic H 2 production.

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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]

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Complexes[edit]

Ean Of Ni Dmg 2 Structure

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.

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)
^