Benzaldehyde oxime

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.

Benzaldehyde oxime
Names

Other names Benzaldoxime
Identifiers
CAS Number	932-90-1^Y (Z): 622-32-2^Y (E): 622-31-1^Y
3D model (JSmol)	(Z): Interactive image (E): Interactive image
ChEMBL	(Z): ChEMBL265435 (E): ChEMBL135583
ChemSpider	(Z): 4481994 (E): 4482130
ECHA InfoCard	100.012.056
EC Number	213-261-2
PubChem CID	(Z): 5324470 (E): 5324611
UNII	(Z): YR8F3Q0KSH (E): TBP7JJ5HTH
CompTox Dashboard (EPA)	DTXSID6061313
InChI (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
SMILES (Z): C1=CC=C(C=C1)\C=N/O (E): C1=CC=C(C=C1)/C=N/O
Properties
Chemical formula	C₇H₇NO
Appearance	White solid
Melting point	(Z) 33 °C (E) 133 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reactions

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

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.