54934-81-5

Basic information

• Product Name: N-(4-bromophenyl)cinnamamide
• Synonyms: N-(4-bromophenyl)cinnamamide;N-(4-Bromophenyl)-3-phenylpropenamide
• CAS NO: 54934-81-5
• Molecular Formula: C₁₅H₁₂BrNO
• Molecular Weight: 302.17
• Mol File: 54934-81-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 472.9 °C at 760 mmHg
• Flash Point: 239.8 °C
• Appearance: /
• Density: 1.455 g/cm³
• Vapor Pressure: 4.13E-09mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: N-(4-bromophenyl)cinnamamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-bromophenyl)cinnamamide(54934-81-5)
• EPA Substance Registry System: N-(4-bromophenyl)cinnamamide(54934-81-5)

Safety Data

• Hazardous Substances Data: 54934-81-5(Hazardous Substances Data)

Usage

General Description

N-(4-Bromophenyl)cinnamamide is a chemical compound that belongs to the class of cinnamamide derivatives. It is a pale yellow solid with a molecular formula C16H12BrNO and a molecular weight of 306.18 g/mol. N-(4-Bromophenyl)cinnamamide is used in various chemical and pharmaceutical applications, including as an intermediate in the synthesis of biologically active molecules. It has also been studied for its potential anti-inflammatory and anti-cancer properties. N-(4-Bromophenyl)cinnamamide is known for its high purity and stability, making it a popular choice for research and industrial purposes.

InChI:InChI=1/C15H12BrNO/c16-13-7-9-14(10-8-13)17-15(18)11-6-12-4-2-1-3-5-12/h1-11H,(H,17,18)/b11-6+

Upstream product

• 86668-30-6 1-Bromo-4-((E)-3-phenyl-propenyl)-benzene 
• 86668-29-3 4-(3-phenylallyl)bromobenzene 
• 106-40-1 4-bromo-aniline 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 205055-71-6 2-chloro-6-chlorosulfonylquinoline 
• 1810-71-5 6-bromo-2-chloroquinoline 
• 1810-66-8 6-bromo-2-quinolone 

Relevant articles and documents

Design of enamides as new selective monoamine oxidase-B inhibitors

Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.

Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity

The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.

A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine

A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine by treatment of various amines is described.