Benzaldehyde oxime

Benzaldehyde oxime
Names
	Other names Benzaldoxime
Identifiers
CAS Number	932-90-1 ; (Z): 622-32-2 ; (E): 622-31-1 ;
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[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). Infobox references

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]

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

Karthikeyan, Parasuraman; Aswar, Sachin Arunrao; Muskawar, Prashant Narayan; Sythana, Suresh Kumar; Bhagat, Pundlik Rambhau; Kumar, Sellappan Senthil; Satvat, Pranveer S. (November 2016). "A novel l-amino acid ionic liquid for quick and highly efficient synthesis of oxime derivatives – An environmental benign approach". Arabian Journal of Chemistry. 9: S1036–S1039. doi:10.1016/j.arabjc.2011.11.007. ISSN 1878-5352.
Kim, Bo Ram; Sung, Gi Hyeon; Kim, Jeum-Jong; Yoon, Yong-Jin (20 April 2013). "A Development of Rapid, Practical and Selective Process for Preparation of Z-Oximes". Journal of the Korean Chemical Society. 57 (2): 295–299. doi:10.5012/jkcs.2013.57.2.295. ISSN 1017-2548.
Johnson, A.K.; Miller, I.D. (January 1976). "Kinetic and mechanistic studies of the rearrangement of benzaldoxime to benzamide catalysed by nickel acetate". Inorganica Chimica Acta. 16: 181–184. doi:10.1016/S0020-1693(00)91710-9. ISSN 0020-1693.
Peng, Xiaoyan; liu, Yutong; Shen, Qing; Chen, Dan; Chen, Xueqin; Fu, Yuning; Wang, Jingxia; Zhang, Xiaobin; Jiang, Hezhong; Li, Jiahong (31 August 2022). "BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light". The Journal of Organic Chemistry. 87 (18): 11958–11967. doi:10.1021/acs.joc.2c00813. eISSN 1520-6904. ISSN 0022-3263. PMID 36044674. S2CID 251979166.
Loupy, André; Régnier, Serge (August 1999). "Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes". Tetrahedron Letters. 40 (34): 6221–6224. doi:10.1016/S0040-4039(99)01159-4. ISSN 0040-4039.
Cherney, Robert J.; Wang, Zhongyu. Preparation of 5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazole derivatives for treatment of autoimmune and chronic inflammatory diseases. 2012 WO 2012061459 A1.

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[1] Karthikeyan, Parasuraman; Aswar, Sachin Arunrao; Muskawar, Prashant Narayan; Sythana, Suresh Kumar; Bhagat, Pundlik Rambhau; Kumar, Sellappan Senthil; Satvat, Pranveer S. (November 2016). "A novel l-amino acid ionic liquid for quick and highly efficient synthesis of oxime derivatives – An environmental benign approach". Arabian Journal of Chemistry. 9: S1036–S1039. doi:10.1016/j.arabjc.2011.11.007. ISSN 1878-5352.

[Bo-2] Kim, Bo Ram; Sung, Gi Hyeon; Kim, Jeum-Jong; Yoon, Yong-Jin (20 April 2013). "A Development of Rapid, Practical and Selective Process for Preparation of Z-Oximes". Journal of the Korean Chemical Society. 57 (2): 295–299. doi:10.5012/jkcs.2013.57.2.295. ISSN 1017-2548.

[3] Johnson, A.K.; Miller, I.D. (January 1976). "Kinetic and mechanistic studies of the rearrangement of benzaldoxime to benzamide catalysed by nickel acetate". Inorganica Chimica Acta. 16: 181–184. doi:10.1016/S0020-1693(00)91710-9. ISSN 0020-1693.

[4] Peng, Xiaoyan; liu, Yutong; Shen, Qing; Chen, Dan; Chen, Xueqin; Fu, Yuning; Wang, Jingxia; Zhang, Xiaobin; Jiang, Hezhong; Li, Jiahong (31 August 2022). "BODIPY Photocatalyzed Beckmann Rearrangement and Hydrolysis of Oximes under Visible Light". The Journal of Organic Chemistry. 87 (18): 11958–11967. doi:10.1021/acs.joc.2c00813. eISSN 1520-6904. ISSN 0022-3263. PMID 36044674. S2CID 251979166.

[5] Loupy, André; Régnier, Serge (August 1999). "Solvent-free microwave-assisted Beckmann rearrangement of benzaldehyde and 2-hydroxyacetophenone oximes". Tetrahedron Letters. 40 (34): 6221–6224. doi:10.1016/S0040-4039(99)01159-4. ISSN 0040-4039.

[6] Cherney, Robert J.; Wang, Zhongyu. Preparation of 5-[3-phenyl-4-(trifluoromethyl)isoxazol-5-yl]-1,2,4-oxadiazole derivatives for treatment of autoimmune and chronic inflammatory diseases. 2012 WO 2012061459 A1.