5439-11-2

Basic information

• Product Name: N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE
• Synonyms: 2-BROMO-N-(2-CHLOROPHENYL)ACETAMIDE;N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE;N-(BROMOACETYL)-2'-CHLOROACETANILIDE;N-(BROMOACETYL)-2'-CHLOROACETANILINE;acetamide, 2-bromo-N-(2-chlorophenyl)-;2-bromo-N-(2-chlorophenyl)ethanamide
• CAS NO: 5439-11-2
• Molecular Formula: C₈H₇BrClNO
• Molecular Weight: 248.5
• Mol File: 5439-11-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 84-87°C
• Boiling Point: 372.1°C at 760 mmHg
• Flash Point: 178.8°C
• Appearance: /
• Density: 1.683g/cm³
• Vapor Pressure: 9.88E-06mmHg at 25°C
• Refractive Index: 1.639
• PKA: 11.60±0.70(Predicted)
• CAS DataBase Reference: N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE(5439-11-2)
• EPA Substance Registry System: N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE(5439-11-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 5439-11-2(Hazardous Substances Data)

Usage

General Description

N1-(2-chlorophenyl)-2-bromoacetamide, also known as 2-Bromo-N-(2-chlorophenyl) acetamide, is a chemical compound that belongs to the class of amides. It is a white to off-white crystalline powder with a molecular formula of C8H7BrClNO and a molecular weight of 242.5 g/mol. N1-(2-CHLOROPHENYL)-2-BROMOACETAMIDE is commonly used in the synthesis of pharmaceuticals and agrochemicals. It also has potential applications in the field of medicinal chemistry, particularly in the development of new drugs. Additionally, it may have uses as an intermediate in the production of other organic compounds. However, it is important to handle this chemical with care as it may have potential health hazards and should be used in a controlled laboratory setting.

InChI:InChI=1/C8H7BrClNO/c9-5-8(12)11-7-4-2-1-3-6(7)10/h1-4H,5H2,(H,11,12)

Upstream product

• 22118-09-8 2-bromoacetyl chloride 
• 95-51-2 o-chloroaniline 
• 79-08-3 bromoacetic acid 
• 598-21-0 2-Bromoacetyl bromide 

Downstream Products

• 1198408-75-1 C₁₉H₁₉ClN₄O 
• 1198408-74-0 N-(2-chlorophenyl)-6-phenylimidazo[1,2-a]pyridine-3-carboxamide 
• 1198408-37-5 C₂₄H₂₇ClN₄O₃ 
• 1198408-38-6 C₂₄H₂₇ClN₄O₄ 
• 1393644-38-6 N-hydroxy-4-{[(2-chlorophenylcarbamoylmethyl)amino]methyl}benzamide 
• 482661-10-9 N-(2-chloro-phenyl)-2-(5-methyl-4-p-tolyl-4H-[1,2,4]triazol-3-ylsulfanyl)-acetamide 
• 116433-50-2 2-Azido-N-(2-chloro-phenyl)-acetamide 
• 496788-10-4 3-amino-N-(2'-chlorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]thieno[3,2-e]pyridine-2-carboxamide 

Relevant articles and documents

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles

Some novel benzimidazole-tethered 1,2,3-triazole derivatives (4a–r) were synthesized by a click reaction between 2-substituted 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one- and two-dimensional nuclear magnetic resonance, Fourier transform infrared, and high-resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds 4a–r exhibited a good-to-moderate α-amylase and α-glucosidase inhibitory activity, with IC50 values ranging from 0.0410 to 0.0916 μmol/ml and 0.0146 to 0.0732 μmol/ml, respectively. Compounds 4e, 4g, and 4n were found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.

Substituted Pyridazin-3(2 H)-ones as Highly Potent and Biased Formyl Peptide Receptor Agonists

Herein we describe the development of a focused series of functionalized pyridazin-3(2H)-one-based formyl peptide receptor (FPR) agonists that demonstrate high potency and biased agonism. The compounds described demonstrated biased activation of prosurvival signaling, ERK1/2 phosphorylation, through diminution of the detrimental FPR1/2-mediated intracellular calcium (Cai2+) mobilization. Compound 50 showed an EC50 of 0.083 μM for phosphorylation of ERK1/2 and an approximate 20-fold bias away from Cai2+ mobilization at the hFPR1.