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Diacetyl monoxime

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Diacetyl monoxime
Names
Other names BDM, Biacetyl monoxime, 2,3-butanedione monoxime
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.316 Edit this at Wikidata
EC Number
  • 200-348-5
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+Key: FSEUPUDHEBLWJY-HWKANZROSA-N
SMILES
  • CC(=NO)C(=O)C
Properties
Chemical formula C4H7NO2
Molar mass 101.105 g·mol
Appearance white solid
Melting point 75–78 °C (167–172 °F; 348–351 K)
Boiling point 185–186 °C (365–367 °F; 458–459 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312, H315, H319, H332, H335
Precautionary statements P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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 inhibiting certain ATPases.

Preparation

The compound can be prepared from butanone by reaction with ethyl nitrite. It is an intermediate in the preparation of dimethylglyoxime:

Uses

Diacetyl monoxime can be used with thiosemicarbazide to selectively detect small amounts of urea in the presence of other nitrogen-containing compounds.

References

  1. Forer, Arthur; Fabian, Lacramioara (2005). "Does 2,3-butanedione monoxime inhibit nonmuscle myosin?". Protoplasma. 225 (1–2): 1–4. doi:10.1007/s00709-004-0077-z. PMID 15868207. S2CID 10475777.
  2. Semon, W. L.; Damerell, V. R. (1930). "Dimethylglyoxime". Organic Syntheses. 10: 22. doi:10.15227/orgsyn.010.0022.
  3. Douglas, L. A.; Bremner, J. M. (1970-02-01). "Colorimetric Determination of Microgram Quantities of Urea". Analytical Letters. 3 (2): 79–87. doi:10.1080/00032717008067782. ISSN 0003-2719.
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