1426540-82-0

Basic information

• Product Name: 2-cyano-ethyl cinnamate
• Synonyms: 2-cyano-ethyl cinnamate
• CAS NO: 1426540-82-0
• Molecular Weight: 201.225
• Mol File: 1426540-82-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-cyano-ethyl cinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyano-ethyl cinnamate(1426540-82-0)
• EPA Substance Registry System: 2-cyano-ethyl cinnamate(1426540-82-0)

Safety Data

• Hazardous Substances Data: 1426540-82-0(Hazardous Substances Data)

Upstream product

• 2039-88-5 2-bromostyrene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 102-92-1 Cinnamoyl chloride 
• 109-78-4 3-Hydroxypropionitrile 
• 140-10-3 cis-cinnamic acid 
• 4610-69-9 (Z)-ethyl cinnamate 
• 100-52-7 benzaldehyde 

Relevant articles and documents

[3,3]-Sigmatropic Rearrangement of Aryl Fluoroalkyl Sulfoxides with Alkyl Nitriles

Herein we report the ortho-cyanoalkylation of aryl fluoroalkyl sulfoxides with alkyl nitriles. The reaction proceeds through an “assembly/deprotonation” triggered [3,3]-rearrangement and allows the incorporation of two valuable functional groups including the cyano group and difluoromethylthio group into arenes. As a consequence, a wide range of ortho-cyanoalkylated difluoromethylthio arenes were produced with high efficiency under mild and environmentally friendly conditions. Remarkably, the reaction proceeds smoothly with the electron-donating group substituted arenes which can be challenging to the reaction of non-fluoroalkyl sulfoxides. This beneficial effect can be attributed to the unique electronegativity of fluoroalkyl substituents.

Key structural features of cis-cinnamic acid as an allelochemical

1-O-cis-cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals isolated from Spiraea thunbergii Sieb. It is suggested that it derives its strong inhibitory activity from cis-cinnamic acid, which is crucial for phytotoxicity. It was synthesized to confirm its structure and bioactivity, and also a series of cis-cinnamic acid analogues were prepared to elucidate the key features of cis-cinnamic acid for lettuce root growth inhibition. The cis-cyclopropyl analogue showed potent inhibitory activity while the saturated and alkyne analogues proved to be inactive, demonstrating the importance of the cis-double bond. Moreover, the aromatic ring could not be replaced with a saturated ring. However, the 1,3-dienylcyclohexene analogue showed strong activity. These results suggest that the geometry of the C-C double bond between the carboxyl group and the aromatic ring is essential for potent inhibitory activity. In addition, using several light sources, the photostability of the cinnamic acid derivatives and the role of the C-C double bond were also investigated.