Chemistry:Benzaldehyde oxime
From HandWiki
| |
| Names | |
|---|---|
| Other names
Benzaldoxime
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL |
|
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| UNII |
|
| |
| |
| 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). | |
| 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.
- ↑ 2.0 2.1 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 et al. (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. ISSN 0022-3263. PMID 36044674.
- ↑ 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.
 |  |
