Acetone oxime

Acetone oxime (acetoxime) is the organic compound with the formula (CH3)2CNOH. It is the simplest example of a ketoxime. It is a white crystalline solid that is soluble in water, ethanol, ether, chloroform, and ligroin. It is used as a reagent in organic synthesis.[2]

Acetone oxime
Names
Preferred IUPAC name
N-Hydroxypropan-2-imine
Other names
Acetoxime; N-Hydroxy-2-propanimine; Methyl methyl ketoxime; 2-Propanone oxime
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.383
EC Number
  • 204-820-1
KEGG
UNII
  • InChI=1S/C3H7NO/c1-3(2)4-5/h5H,1-2H3
    Key: PXAJQJMDEXJWFB-UHFFFAOYSA-N
  • InChI=1/C3H7NO/c1-3(2)4-5/h5H,1-2H3
    Key: PXAJQJMDEXJWFB-UHFFFAOYAK
  • CC(=NO)C
Properties
C3H7NO
Molar mass 73.095 g·mol−1
Appearance White needle like crystals
Density 0.901 g/mL[1]
Melting point 60 to 63 °C (140 to 145 °F; 333 to 336 K)
Boiling point 135 °C (275 °F; 408 K)
330 g/L (20 °C)
-44.42·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 May be harmful if swallowed
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H228, H302, H317, H318, H351
P201, P202, P210, P240, P241, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P370+P378, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
0
0
Flash point 60 °C (140 °F; 333 K)
Lethal dose or concentration (LD, LC):
4,000 mg/kg Intraperitoneal-mouse
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetone oxime (acetoxime) was first prepared and named in 1882 by the German chemist Victor Meyer and his Swiss student Alois Janny.[3]

Preparation

Acetone oxime is synthesized by the condensation of acetone and hydroxylamine in the presence of HCl:[4][2]

(CH3)2CO + H2NOH → (CH3)2CNOH + H2O

It can also be generated via ammoxidation of acetone in the presence of hydrogen peroxide.[5]

Uses

Acetone oxime is an excellent corrosion inhibitor (deoxidant) with lower toxicity and greater stability compared to the common agent hydrazine. It is also useful in the determination of ketones, cobalt and in organic synthesis.[6]

References
  1. Sigma-Aldrich Chemical Catalogue "Acetone Oxime". Retrieved 2 September 2016.
  2. Steven M. Weinreb, Kristina Borstnik "Acetone Oxime" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007. doi:10.1002/047084289X.rn00765
  3. Meyer, Victor; Janny, Alois (1882). "Ueber die Einwirkung von Hydroxylamin auf Aceton" [On the effect of hydroxylamine on acetone]. Berichte der Deutschen Chemischen Gesellschaft (in German). 15: 1324–1326. doi:10.1002/cber.188201501285. From p. 1324: "Die Substanz, welche wir, wegen ihrer nahen Beziehungen zur Acetoximsäure, und da sie keine sauren Eigenschaften besitzt, vorläufig Acetoxim nennen wollen, …" (The substance, which we – on account of its close relations to acetoximic acid, and since it possesses no acid properties – will, for the present, name "acetoxime," … )
  4. Handbook of Chemistry and Physics "Acetone Oxime". Archived from the original on 24 July 2017. Retrieved 23 April 2014.
  5. Xinhua Liang, Zhentao Mi, Yaquan Wang, Li Wang, Xiangwen Zhang "Synthesis of acetone oxime through acetone ammoximation over TS-1" Reaction Kinetics and Catalysis Letters Volume 82, pp 333-337. .
  6. Acetone Oxime Properties, additional text.
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