Diacetyl 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 inhibiting certain ATPases.^[1]

Diacetyl monoxime

Names
Other names BDM, Biacetyl monoxime, 2,3-butanedione monoxime
Identifiers
CAS Number	17019-25-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4480
ChEMBL	ChEMBL1255578
ChemSpider	4917792
ECHA InfoCard	100.000.316
EC Number	200-348-5
KEGG	C07509
PubChem CID	6409633
UNII	19SQ93LM6H Y
CompTox Dashboard (EPA)	DTXSID7024669
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−1
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
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 [77 °F], 100 kPa). Infobox references

Preparation

The compound can be prepared from butanone by reaction with ethyl nitrite. It is an intermediate in the preparation of dimethylglyoxime:^[2]

Uses

Diacetyl monoxime can be used with thiosemicarbazide to selectively detect small amounts of urea in the presence of other nitrogen-containing compounds.^[3]

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.