1-(2-Bromo-4-chlorophenyl)ethanone

Base Information

• Chemical Name: 1-(2-Bromo-4-chlorophenyl)ethanone
• CAS No.: 825-40-1
• Molecular Formula: C8H6 Br Cl O
• Molecular Weight: 233.492
• Hs Code.: 2914700090
• European Community (EC) Number: 672-231-0
• DSSTox Substance ID: DTXSID80405736
• Wikidata: Q72452292
• Mol file: 825-40-1.mol

Synonyms:1-(2-bromo-4-chlorophenyl)ethanone;825-40-1;2-Bromo-4-chloroacetophenone;4-acetyl-3-bromo-1-chlorobenzene;MFCD02683063;Ethanone, 1-(2-bromo-4-chlorophenyl)-;Ethanone,1-(2-bromo-4-chlorophenyl)-;SCHEMBL616449;DTXSID80405736;URBATMJMOGHOCE-UHFFFAOYSA-N;AMY16029;AKOS015891315;CS-W004840;AC-28641;DS-15914;SY057517;FT-0632996;A56001;2 inverted exclamation mark -Bromo-4 inverted exclamation mark -chloroacetophenone

Chemical Property of 1-(2-Bromo-4-chlorophenyl)ethanone

Chemical Property:

• Vapor Pressure: 0.00137mmHg at 25°C
• Melting Point: 44 °C
• Boiling Point: 297.2°C at 760 mmHg
• Flash Point: 133.6°C
• PSA: 17.07000
• Density: 1.566g/cm³
• LogP: 3.30510
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 231.92906
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

97% ^*data from raw suppliers

2-Bromo-4-chloroacetophenone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C=C(C=C1)Cl)Br

Technology Process of 1-(2-Bromo-4-chlorophenyl)ethanone

There total 4 articles about 1-(2-Bromo-4-chlorophenyl)ethanone 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: 65.0%

1-(2-bromo-4-chlorophenyl)ethanol (1086601-87-7) → 2-bromo-p-chloroacetophenone (825-40-1)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1002/anie.202002289

Reference yield:

2-bromo-4-chlorobenzaldehyde (84459-33-6) → 2-bromo-p-chloroacetophenone (825-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 3 h / 0 °C / Inert atmosphere

2: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C

With silica gel; pyridinium chlorochromate; In diethyl ether; dichloromethane;

DOI:10.1021/acs.orglett.5b02703

Reference yield:

2-bromo-4-chlorobenzoic acid (936-08-3) + methylmagnesium bromide (75-16-1) → 2-bromo-p-chloroacetophenone (825-40-1)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03303

upstream raw materials:

2-bromo-4-chlorobenzaldehyde

1-(2-bromo-4-chlorophenyl)ethanol

2-bromo-4-chlorobenzoic acid

methylmagnesium bromide

Downstream raw materials:

2-(bromomethyl)-4-(2-chlorophenyl)-2-(4-chlorophenyl)-1,3-dioxolane

6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

4-chlorobenzoylmethylenetriphenylphosphorane

C₈H₇BrClNO

Refernces

One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I₂ as a condensation agent

10.1055/s-2004-829118

The research aims to develop a new and simple method for synthesizing symmetrical 1,4-diketones from α-halo ketones using zinc and iodine as condensation agents. The study reports the successful preparation of eleven 1,4-diphenylbutane-1,4-diones from corresponding α-halo acetophenones under mild conditions (65 °C) with moderate to high yields. The key chemicals used include various α-halo ketones such as 2-bromo-1-phenyl-ethanone and 2-bromo-4'-chloroacetophenone, along with zinc dust and a small amount of iodine. The reaction mechanism is explained through a Wurtz-like self-condensation pathway, where the initial reduction of α-bromo ketones by zinc forms enolate-like anions, which then attack another α-carbon of the ketone to form the 1,4-diketone products. The study concludes that this method is advantageous due to its mild reaction conditions and higher yields compared to previous methods, making it a useful approach for the preparation of functionalized symmetrical 1,4-diketones, which are important intermediates in the synthesis of five-membered carbocyclic and heterocyclic compounds.