4-Chloro-2'-bromoacetophenone

Base Information

• Chemical Name: 4-Chloro-2'-bromoacetophenone
• CAS No.: 536-38-9
• Molecular Formula: C8H6BrClO
• Molecular Weight: 233.492
• Hs Code.: 29147000
• European Community (EC) Number: 208-631-5
• NSC Number: 8452
• UNII: 2R0V40DI4R
• DSSTox Substance ID: DTXSID7060209
• Nikkaji Number: J71.685E
• Wikidata: Q27255497
• ChEMBL ID: CHEMBL140061
• Mol file: 536-38-9.mol

Synonyms:Acetophenone,2-bromo-4'-chloro- (6CI,7CI,8CI);1-(4-Chlorophenyl)-2-bromo-1-ethanone;2-Bromo-1-(4-chlorophenyl)-1-ethanone;2-Bromo-4'-chloroacetophenone;2-Bromo-p-chloroacetophenone;2'-Bromo-4-chloroacetophenone;4-Chloro-a-bromoacetophenone;4-Chloro-w-bromoacetophenone;4'-Chloro-2-bromoacetophenone;4'-Chlorophenacyl bromide;Bromomethyl4-chlorophenyl ketone;Bromomethyl p-chlorophenyl ketone;NSC 8452;p-(Bromoacetyl)chlorobenzene;p-Chloro-w-bromoacetophenone;p-Chlorophenacyl bromide;a-Bromo-4-chloroacetophenone;w-Bromo-p-chloroacetophenone;

Chemical Property of 4-Chloro-2'-bromoacetophenone

Chemical Property:

• Appearance/Colour: crystalline powder
• Vapor Pressure: 0.00216mmHg at 25°C
• Melting Point: 95-99 °C
• Refractive Index: 1.584
• Boiling Point: 289.7 °C at 760 mmHg
• Flash Point: 129 °C
• PSA: 17.07000
• Density: 1.598 g/cm³
• LogP: 2.91760
• Storage Temp.: Keep Cold
• Sensitive.: Lachrymatory
• Solubility.: soluble in Methanol
• Water Solubility.: Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 231.92906
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

≥99.50% ^*data from raw suppliers

4-Chlorophenylacylbromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-22-36
• Safety Statements: 26-36/37/39-45-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)CBr)Cl
• Uses: In the preparation of quaternary salts of methenamine and of chlorophenol glyoximes. 2-Bromo-4'-chloroacetophenone is used as pharmaceutical intermediate.

Technology Process of 4-Chloro-2'-bromoacetophenone

There total 34 articles about 4-Chloro-2'-bromoacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

1-(bromoethynyl)-4-chlorobenzene (33491-03-1) → 4-chlorobenzoylmethyl bromide (536-38-9)

Guidance literature:

With water; copper(II) acetate monohydrate; trifluoroacetic acid; at 70 ℃; for 6h; chemoselective reaction;

DOI:10.1002/ejoc.201501198

Reference yield: 93.0%

2-bromo-1-(4-chlorophenyl)ethanol (6314-52-9) → 4-chlorobenzoylmethyl bromide (536-38-9)

Guidance literature:

With tert.-butylhydroperoxide; In ethanol; water; at 20 ℃; for 12h; Inert atmosphere; Irradiation;

DOI:10.1039/d1gc01729b

Reference yield: 91.0%

para-chloroacetophenone (99-91-2) → 2,2-dibromo-1-(4-chlorophenyl)ethanone (13651-12-2) + 4-chlorobenzoylmethyl bromide (536-38-9)

Guidance literature:

With N-Bromosuccinimide; silica gel; In methanol; for 0.316667h; chemoselective reaction; Reflux;

DOI:10.1016/j.cclet.2013.09.014

upstream raw materials:

para-chloroacetophenone

2-bromoacetyl chloride

chlorobenzene

4-chloro-α-bromoacetophenone methyl hemiacetal

Downstream raw materials:

1,1'-bis-(4-chloro-phenyl)-2,2'-piperazine-1,4-diyl-bis-ethanone

1-(2-(4-chlorophenyl)-2-oxoethyl)pyridinium bromide

1-(2-(4-chlorophenyl)-2-oxoethyl)-2-methylpyridinium bromide

1-(4-chloro-phenacyl)-3-hydroxy-pyridinium; bromide

Refernces

• 1、 Tu, Dewei,Luo, Juan,Jiang, Wengao,Tang, Qiang. "Solvent-free preparation of α,α-dichloroketones with sulfuryl chloride". supporting information. . Retrieved 2021/09/15.
• 2、 Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng. "A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions". supporting information. p. 429 - 432. Retrieved 2020/02/29.