20772-12-7

Basic information

• Product Name: 1-bromo-3-phenylpropan-2-one
• Synonyms: 1-bromo-3-phenylpropan-2-one;2-Propanone, 1-broMo-3-phenyl-;1-BroMo-3-phenyl-2-propanone
• CAS NO: 20772-12-7
• Molecular Formula: C₉H₉BrO
• Molecular Weight: 213
• Product Categories: Aromatics, Intermediate
• Mol File: 20772-12-7.mol
• Article Data: 23

Chemical Properties

• Melting Point: 58 °C
• Boiling Point: 270.941°C at 760 mmHg
• Flash Point: 79.57°C
• Appearance: /
• Density: 1.429g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: 1-bromo-3-phenylpropan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-3-phenylpropan-2-one(20772-12-7)
• EPA Substance Registry System: 1-bromo-3-phenylpropan-2-one(20772-12-7)

Safety Data

• Hazardous Substances Data: 20772-12-7(Hazardous Substances Data)

Usage

Description

1-bromo-3-phenylpropan-2-one is an organic compound that features a bromine atom and a phenyl group attached to a propanone structure. It is a valuable synthetic intermediate due to its unique chemical properties and reactivity.

Uses

1-bromo-3-phenylpropan-2-one is used as a synthetic intermediate for the production of various pharmaceutical agents. Its application is primarily in the synthesis of tyrosine kinase inhibitors and antiangiogenic agents, which are important in the treatment of cancer.
Used in Pharmaceutical Industry:
1-bromo-3-phenylpropan-2-one is used as a key intermediate in the synthesis of tyrosine kinase inhibitors for the Pharmaceutical Industry. These inhibitors play a crucial role in blocking the activity of tyrosine kinases, which are enzymes often overexpressed in cancer cells, thereby contributing to the uncontrolled growth and proliferation of these cells.
Additionally, 1-bromo-3-phenylpropan-2-one is used as a precursor in the development of antiangiogenic agents within the Pharmaceutical Industry. Antiangiogenic agents work by inhibiting the formation of new blood vessels, which is a process that cancer cells exploit to grow and spread. By disrupting this process, these agents can limit the growth and metastasis of tumors.

InChI:InChI=1/C9H9BrO/c10-7-9(11)6-8-4-2-1-3-5-8/h1-5H,6-7H2

Upstream product

• 28988-98-9 1-bromo-3-phenylpropan-2-ol 
• 186581-53-3 diazomethane 
• 103-80-0 phenylacetyl chloride 
• 300-57-2 allylbenzene 
• 95547-16-3 1-Phenyl-3-(trimethylsilyl)propan-2-one 
• 67396-36-5 (3-bromoprop-2-yn-1-yl)benzene 
• 103-79-7 1-phenyl-acetone 
• 4250-02-6 1-diazo-3-phenyl-2-propanone 
• 103-82-2 phenylacetic acid 
• 1555-80-2 phenylacetic anhydride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 24193-22-4 (+/-)-(2S,3R)-2-(bromomethyl)-3-phenyloxirane 
• 591-50-4 iodobenzene 
• 1589-82-8 phenylmagnesium bromide 

Downstream Products

• 23022-83-5 1-bromo-1-phenyl-2-propanone 
• 7496-56-2 2-amino-4-benzylthiazole 
• 135608-75-2 benzyl carbamate 
• 144449-06-9 2-benzyl-6-chloroimidazo<1,2-b>pyridazine 
• 144449-10-5 2-benzyl-6-phenylthioimidazo<1,2-b>pyridazine 
• 85656-42-4 4-benzyl-2-dimethylaminothiazole 
• 76467-29-3 N-Methyl-N-(2-oxo-3-phenyl-propyl)-formamide 
• 85656-43-5 4-benzyl-2-(N-benzyl-N-methylamino)thiazole 
• 144449-07-0 2-benzyl-6-(2'-methoxyphenoxy)imidazo<1,2-b>pyridazine 
• 57740-65-5 Oxalsaeure-(ethyl)(2-oxo-3-phenylpropyl)ester 
• 58265-79-5 bis(benzoylmethyl)butane-1,4-dioate 
• 77463-49-1 bis(benzoylmethyl) 2,2-dimethylpropane-1,3-dioate 
• 77463-50-4 (2-Oxo-2-phenyl-ethoxycarbonylmethylsulfanyl)-acetic acid 2-oxo-2-phenyl-ethyl ester 
• 144449-09-2 2-benzyl-6-(4'-chlorophenoxy)imidazo<1,2-b>pyridazine 

Relevant articles and documents

Regiospecific synthesis of unsymmetrical α-bromoketones

A convenient regiospecific preparation of unsymmetrical α-bromoketones, commencing from Meldrum's acid, has been developed. This procedure allows for preparation of α-bromoketones which are unobtainable in a pure state by other bromination methods and is

Synthesis of 4-(3-oxo-3-phenylpropyl)morpholin-4-ium chloride analogues and their inhibitory activities of nitric oxide production in lipopolysaccharide-induced BV2 cells

Based on our previous report that 3-morpholino-1-phenylpropan-1-one 2, one of the fluoxetine's simplified morpholino analogue, inhibited nitric oxide (NO) production, in this paper, various substituted benzene analogues with morpholine hydrochloride of 2 were synthesized and their inhibitory effects on NO production in lipopolysaccharide (LPS)-induced BV2 cells were tested. Among the synthesized compounds, 2-trifluoromethyl analogue 16n (IC50 = 8.6 μM) showed a significantly higher inhibitory activity than that of the parent compound 2a (IC50 > 50 μM) and suppressed NO production dose-dependently without cytotoxicity. Compound 16n also inhibited iNOS expression in LPS-induced BV2 cells at 2, 10 and 20 μM concentrations. These results suggest that compound 16n inhibited NO production by suppressing the expression of iNOS and can be used as a lead structure for developing new inhibitor of NO production.

Design, synthesis, SAR and biological investigation of 3-(carboxymethyl)rhodanine and aminothiazole inhibitors of Mycobacterium tuberculosis Zmp1

Sixteen 3-(carboxymethyl)rhodanines, and twelve aminothiazoles as rhodanine-mimetics were designed, synthesized and tested as inhibitors of the Zmp1 enzyme from Mycobacterium tuberculosis (Mtb). Almost all rhodanines (5a–d, 5f–n, and 7a–b) exhibited Zmp1 inhibition with IC50 values in the range 1.3–43.9 μM, whereas only aminothiazoles 12b and 12d proved active with IC50 values of 41.3 and 35.7 μM, respectively. Structure-activity relationships (SAR) were coupled with molecular modeling studies to highlight structural determinants for Zmp1 inhibition. Moreover, rhodanines 5a and 5c induced 23.4 and 53.8% of Mtb growth inhibition in THP-1 infected cells, respectively, at the non-toxic concentration of 10 μg/ml. This work represents a step forward in targeting Zmp1 by small molecules.