Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Benzaldehyde oxime

From Wikipedia, the free encyclopedia
Benzaldehyde oxime
Names
Other names
Benzaldoxime
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.012.056Edit 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
AppearanceWhite solid
Melting point(Z) 33 °C[1]
(E) 133 °C[2]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Benzaldehyde oxime is anorganic compound with the formula C7H7NO. Benzaldehyde oxime can be synthesized frombenzaldehyde andhydroxylamine hydrochloride in presence of a base. The reaction at room temperature inmethanol gives 9%E-isomer and 82%Z-isomer.[2]

Reactions

[edit]

Benzaldehyde oxime undergoesBeckmann rearrangement to formbenzamide, catalyzed bynickel salts[3] or photocatalyzed byBODIPY.[4] Its dehydration yieldsbenzonitrile. It can be hydrolyzed to regenerate benzaldehyde.[5]

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

References

[edit]
  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.
  2. ^abKim, 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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Benzaldehyde_oxime&oldid=1244475367"
Category:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp