Dimethylglyoxime is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

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 di

oxime In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R’ may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted ...

derivative of the di

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

butane-2,3-dione (also known as

diacetyl Diacetyl (IUPAC systematic name: butanedione or butane-2,3-dione) is an organic compound with the chemical formula (CH3CO)2. It is a yellow liquid with an intensely buttery flavor. It is a vicinal diketone (two C=O groups, side-by-side). Diacet ...

). DmgH₂ is used in the analysis of

palladium Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself na ...

nickel Nickel is a chemical element with symbol Ni and atomic number 28. It is a silvery-white lustrous metal with a slight golden tinge. Nickel is a hard and ductile transition metal. Pure nickel is chemically reactive but large pieces are slow to ...

. Its

coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

es are of theoretical interest as models for enzymes and as catalysts. Many related

ligands In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electro ...

can be prepared from other diketones, e.g.

benzil Benzil (i.e. Bz2, systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula ( C6H5 CO)2, generally abbreviated ( PhCO)2. This yellow solid is one of the most common diketones. Its main use is as a photoinitia ...

Preparation

Dimethylglyoxime can be prepared from

butanone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in ...

first by reaction with

ethyl nitrite The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol. : Uses It is used as a reagent with butanone to yield the dimethylglyoxime end product. Ethyl nitrite is the main ingre ...

to give

biacetyl monoxime Diacetyl monoxime is a chemical compound described by the formula CH3C(O)C(NOH)CH3. This colourless solid is the monooxime derivative of the diketone butane-2,3-dione (also known as diacetyl and biacetyl). Its biological effects include inhibitin ...

. The second

is installed using sodium

hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ...

monosulfonate: Preparation_of_dimethylglyoxime

Complexes

Dimethylglyoxime forms complexes with metals including

and

cobalt Cobalt is a chemical element with the symbol Co and atomic number 27. As with nickel, cobalt is found in the Earth's crust only in a chemically combined form, save for small deposits found in alloys of natural meteoric iron. The free element, pr ...

. These complexes are used to separate those cations from solutions of metal salts and in

gravimetric analysis Gravimetric analysis describes a set of methods used in analytical chemistry for the quantitative determination of an analyte (the ion being analyzed) based on its mass. The principle of this type of analysis is that once an ion's mass has been ...

. It is also used in

precious metals refining In metallurgy, refining consists of purifying an impure metal. It is to be distinguished from other processes such as smelting and calcining in that those two involve a chemical change to the raw material, whereas in refining, the final materia ...

to precipitate

from solutions of

palladium chloride Palladium(II) chloride, also known as palladium dichloride and palladous chloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value ...

References

{{Authority control Ketoximes Chelating agents