Formaldoxime

Formaldoxime
Names
Preferred IUPAC name
N-Hydroxymethanimine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.769 Edit this at Wikidata
EC Number
  • 200-845-7
UNII
  • InChI=1S/CH3NO/c1-2-3/h3H,1H2
    Key: SQDFHQJTAWCFIB-UHFFFAOYSA-N
  • C=NO
Properties
H2C=N−OH
Molar mass 45.041 g·mol−1
Appearance colorless liquid
Melting point 2.5 °C (36.5 °F; 275.6 K)
Boiling point 84 °C (183 °F; 357 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Formaldoxime is the organic compound with the formula H2C=N−OH. It is the oxime of formaldehyde. A colorless liquid, the pure compound tends to polymerize into a cyclic trimer. Aqueous solutions are stable as is the formaldoxime hydrochloride ([H2C=N(−H)(−OH)]+Cl−). It is a reagent in organic synthesis for the conversion of aryl diazonium salts to aryl aldehydes.[1]

It is generated by combining hydroxylamine and formaldehyde.[2]

References

  1. ^ De Kimpe, Norbert (2001). "Formaldoxime". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rf023. ISBN 0-471-93623-5.
  2. ^ S. D. Jolad, S. Rajagopalan (1966). "2-Bromo-4-methylbenzaldehyde". Org. Synth. 46: 13. doi:10.15227/orgsyn.046.0013.

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