Dimethylglyoxime

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Dimethylglyoxime
Dimethylglyoxime
Dimethylglyoxime-3D-balls.png
Names
IUPAC name
N,N′-Dihydroxy-2,3-butanediimine
Other names
  • Dimethylglyoxime
  • Diacetyl dioxime
  • Butane-2,3-dioxime
  • Chugaev's reagent
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.201 Edit this at Wikidata
EC Number
  • 202-420-1
RTECS number
  • EK2975000
UNII
  • InChI=1S/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+ checkY
    Key: JGUQDUKBUKFFRO-CIIODKQPSA-N checkY
  • InChI=1/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3-,6-4+
    Key: JGUQDUKBUKFFRO-CIIODKQPBA
  • C\C(=N\O)\C(\C)=N\O
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
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, Skin/Eye Irritant
GHS labelling:
GHS02: FlammableGHS06: Toxic
Danger
H228, H301
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).
checkY verify (what is checkY☒N ?)
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]

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]

Preparation of dimethylglyoxime.png

Complexes[edit]

Dimethylglyoxime forms complexes with metals including nickel,[2] palladium and cobalt.[3] 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.

References[edit]

  1. ^ Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.
  2. ^ Lev Tschugaeff (1905). "Über ein neues, empfindliches Reagens auf Nickel". Berichte der Deutschen Chemischen Gesellschaft. 38 (3): 2520–2522. doi:10.1002/cber.19050380317.
  3. ^ Girolami, G. S.; Rauchfuss, T.B.; Angelici, R. J. (1999). Synthesis and Technique in Inorganic Chemistry: A Laboratory Manual (3rd ed.). pp. 213–215.