Acetone oxime

Acetone oxime
Names
IUPAC name
2-Propanone oxime
Other names
Acetoxime; N-Hydroxy-2-propanimine; Methyl methyl ketoxime
Identifiers
127-06-0
3D model (Jmol) Interactive image
ChEBI CHEBI:15349
ChemSpider 60524
ECHA InfoCard 100.004.383
EC Number 204-820-1
KEGG C01995
PubChem 67180
Properties
C3H7NO
Molar mass 73.10 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)
Hazards
Main hazards May be harmful if swallowed
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 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) 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]

Preparation

Acetone oxime is synthesized by the condensation of acetone and hydroxylamine in the presence of HCl:[3][2]

(CH3)2CO + H2NOH → (CH3)2CNOH + H2O

It can also be generated via ammoxidation of acetone in the presence of hydrogen peroxide.[4]

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.[5]

References

  1. ↑ Sigma-Aldrich Chemical Catalogue "Acetone Oxime". Retrieved 2 September 2016.
  2. 1 2 Steven M. Weinreb, Kristina Borstnik "Acetone Oxime" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007. doi:10.1002/047084289X.rn00765
  3. ↑ Handbook of Chemistry and Physics "Acetone Oxime". Retrieved 23 April 2014.
  4. ↑ 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. .
  5. ↑ Acetone Oxime Properties, additional text.
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