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Dimethylglyoxime

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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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.201 Edit this at Wikidata
EC Number
  • 202-420-1
PubChem CID
RTECS number
  • EK2975000
UNII
CompTox Dashboard (EPA)
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
Appearance White/Off White Powder
Density 1.37 g/cm
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 GHS02: FlammableGHS06: Toxic
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability (red): no hazard codeInstability (yellow): no hazard codeSpecial hazards (white): no code
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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:

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

Complexes

Dimethylglyoxime forms complexes with metals including nickel, palladium and cobalt. 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

References

  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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