Benzaldehyde oxime

Chemical compound From Wikipedia, the free encyclopedia

Benzaldehyde oxime is an organic compound with the formula C7H7NO. Benzaldehyde oxime can be synthesized from benzaldehyde and hydroxylamine hydrochloride in presence of a base. The reaction at room temperature in methanol gives 9% E-isomer and 82% Z-isomer.[2]

Quick facts Names, Identifiers ...
Benzaldehyde oxime
Names
Other names
Benzaldoxime
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.012.056 Edit this at Wikidata
EC Number
  • 213-261-2
UNII
  • (Z): InChI=1S/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H/b8-6-
    Key: VTWKXBJHBHYJBI-VURMDHGXSA-N
  • (E): InChI=1S/C7H7NO/c9-8-6-7-4-2-1-3-5-7/h1-6,9H/b8-6+
    Key: VTWKXBJHBHYJBI-SOFGYWHQSA-N
  • (Z): C1=CC=C(C=C1)\C=N/O
  • (E): C1=CC=C(C=C1)/C=N/O
Properties
C7H7NO
Appearance White solid
Melting point (Z) 33 °C[1]
(E) 133 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Reactions

Benzaldehyde oxime undergoes Beckmann rearrangement to form benzamide, catalyzed by nickel salts[3] or photocatalyzed by BODIPY.[4] Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate benzaldehyde.[5]

It reacts with N-chlorosuccinimide in DMF to form benzohydroximoyl chloride, in which chlorine replaces hydrogen on the carbon attached to the nitrogen in benzaldehyde oxime.[6]

References

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