74860-13-2

Basic information

• Product Name: 2-(4-bromophenyl)acetamide
• Synonyms: 2-(4-bromophenyl)acetamide;BenzeneacetaMide, 4-broMo-;4-Bromobenzeneacetamide;4-Bromophenylacetamide;NSC 84540
• CAS NO: 74860-13-2
• Molecular Formula: C₈H₈BrNO
• Molecular Weight: 214.07
• Mol File: 74860-13-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 197-198℃
• Boiling Point: 376.9°C at 760 mmHg
• Flash Point: 181.8°C
• Appearance: /
• Density: 1.537g/cm³
• Vapor Pressure: 7E-06mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: 2-8°C
• PKA: 16.12±0.40(Predicted)
• CAS DataBase Reference: 2-(4-bromophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenyl)acetamide(74860-13-2)
• EPA Substance Registry System: 2-(4-bromophenyl)acetamide(74860-13-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 74860-13-2(Hazardous Substances Data)

Usage

General Description

2-(4-bromophenyl)acetamide, also known as 1-(4-bromophenyl)ethanone-1-amine, is a chemical compound with the molecular formula C8H8BrNO. This substance appears as white, crystalline, odourless solids. In terms of its chemical structure, it consists of an acetamide group attached to a 4-bromophenyl group. 2-(4-bromophenyl)acetamide is often used in the production of various pharmaceuticals and is usually prepared in a laboratory setup by reacting 4-bromophenylacetic acid with an appropriate amine. While it has several beneficial scientific and industrial applications, this chemical compound is not commonly found in nature or in household substances.

InChI:InChI=1/C8H8BrNO/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H2,10,11)

Upstream product

• 103-81-1 Benzeneacetamide 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 27200-79-9 p-bromophenylacetaldehyde 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 120157-97-3 t-butyl 2-(4-bromophenyl)ethylcarbamate 
• 73918-56-6 4-Bromophenethylamine 
• 90-04-0 2-methoxy-phenylamine 
• 120158-10-3 [2-(4-Bromo-phenyl)-acetyl]-carbamic acid tert-butyl ester 
• 16532-79-9 4-Bromophenylacetonitrile 
• 26069-13-6 2,6-Dimethylen-bicyclo[3.3.1]nonan 
• 4203-30-9 1-(4-bromo-phenyl)-2-diazo-ethanone 
• 37859-24-8 2-(4-bromophenyl)acetyl chloride 

Downstream Products

• 98946-72-6 (4-bromo-phenyl)-acetic acid-(2,2,2-trichloro-1-hydroxy-ethylamide) 
• 4654-39-1 4-bromophenethanol 
• 16532-79-9 4-Bromophenylacetonitrile 
• 147111-30-6 2-(4-bromophenyl)ethanethioamide 
• 98434-52-7 (2,4,6-tribromo-phenyl)-acetic acid amide 
• 68819-83-0 methyl N-(4-bromobenzyl)carbamate 
• 1243290-20-1 N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-2,2-dimethylpropyl)-2-(4-bromophenyl)acetamide 
• 697746-47-7 3-[4-(aminocarbonyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide 
• 176961-56-1 2-(4-bromobenzyl)-oxazole 

Relevant articles and documents

Hydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism

The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these experimental findings and density functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water molecule to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water molecule in the vicinity of the C(sp) atom of the nitrile.

Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor

Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.