64741-15-7

Basic information

• Product Name: N-(3-chlorophenyl)-3-phenylprop-2-enamide
• CAS NO: 64741-15-7
• Molecular Formula: C₁₅H₁₂ClNO
• Molecular Weight: 257.7149
• Mol File: 64741-15-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 456.4°C at 760 mmHg
• Flash Point: 229.8°C
• Density: 1.267g/cm³
• Vapor Pressure: 1.63E-08mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: N-(3-chlorophenyl)-3-phenylprop-2-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-chlorophenyl)-3-phenylprop-2-enamide(64741-15-7)
• EPA Substance Registry System: N-(3-chlorophenyl)-3-phenylprop-2-enamide(64741-15-7)

Safety Data

• Hazardous Substances Data: 64741-15-7(Hazardous Substances Data)

Upstream product

• 102-92-1 cinnamoyl chloride 
• 108-42-9 3-chloro-aniline 
• 621-82-9 Cinnamic acid 
• 15386-81-9 N-(3-chlorophenyl)malonamic acid 
• 100-52-7 benzaldehyde 
• 102-92-1 Cinnamoyl chloride 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 2909-38-8 m-chlorophenyl isocyanate 
• 140-10-3 (E)-3-phenylacrylic acid 

Relevant articles and documents

Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors

A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 μM, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.

Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations

A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.

Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates

A new and effective method for the preparation of a variety of olefinic carboxamides 6a-k and N-(4-methylphenylsulfonyl)carboxamides 7a-d is described.The reaction of aryl and alkyl isocyanates 4a-c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a-e and di-1-alkenyldibutylstannanes 2a-c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a-k or the N-(4-methylphenylsulfonyl)-substituted olefinic carboxamides 7a-d in good yields.The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system.In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation. - Key Words: Electrophilic vinylic substitution / Isocyanates / α,β-Unsaturated amides, synthesis of / Carbodestannylation / Alkenylstannanes, applications of