139-27-5

Basic information

• Product Name: APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE
• Synonyms: APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE;1-(3-Benzoyloxy)phenyl)-2-bromoethanone;1-bromo-4'-benzoyloxy acid;-Bromo-m-benzoyloxyacetophenone;A-Bromo-M-Benzoyloxyacetophenone
• CAS NO: 139-27-5
• Molecular Formula: C₁₅H₁₁BrO₃
• Molecular Weight: 319.15004
• Mol File: 139-27-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 432.6°Cat760mmHg
• Flash Point: 215.4°C
• Appearance: /
• Density: 1.466g/cm³
• CAS DataBase Reference: APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE(139-27-5)
• EPA Substance Registry System: APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE(139-27-5)

Safety Data

• Hazardous Substances Data: 139-27-5(Hazardous Substances Data)

Usage

General Description

Alpha-Bromo-M-Benzoyloxyacetophenone, also known as alpha-bromo-3',4'-methylenedioxybenzophenone, is a chemical compound. It is a white to off-white crystalline powder with a chemical formula of C15H11BrO3. APLPHA-BROMO-M-BENZOYLOXYACETOPHENONE is primarily used in the production of pharmaceuticals and dyes, as well as in organic synthesis. It is known for its use as an intermediate in the manufacture of other organic compounds, and it is also used as a photoinitiator in the production of UV-curable materials. Additionally, alpha-bromo-m-benzoyloxyacetophenone has been found to exhibit antifungal and antibacterial properties, making it a versatile and valuable chemical in various industries.

Synthetic route

3-acetylphenyl benzoate (139-28-6) + phenyltrimethylammonium tribromide (4207-56-1) → 3-benzoyloxy-ω-bromoacetophenone (139-27-5)

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	62%

3-acetylphenyl benzoate (139-28-6) → 3-benzoyloxy-ω-bromoacetophenone (139-27-5)

Conditions	Yield
With bromine

3-Hydroxyacetophenone (121-71-1) → 3-benzoyloxy-ω-bromoacetophenone (139-27-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: bromine View Scheme

benzoyl chloride (98-88-4) → 3-benzoyloxy-ω-bromoacetophenone (139-27-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: bromine View Scheme

3-benzoyloxy-ω-bromoacetophenone (139-27-5) + dibenzylamine (103-49-1) → 3-benzoyloxy-ω,ω-(dibenzylamino)acetophenone hydrochloride

Conditions	Yield
In benzene at 20℃; for 5h; Substitution;	75%

3-benzoyloxy-ω-bromoacetophenone (139-27-5) → 2-azido-1-(3-benzoyloxy-phenyl)-ethanone (857561-03-6)

Conditions	Yield
With sodium azide; ethanol

2-(piperidin-4-yl)ethyl chloride (1932-03-2) + 3-benzoyloxy-ω-bromoacetophenone (139-27-5) + (2,4-dihydroxy-phenyl)-naphthalen-1-yl-methanone → (6-hydroxy-3-naphthalen-1-yl-benzofuran-2-yl)-[3-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

Conditions	Yield
Multistep reaction;

3-benzoyloxy-ω-bromoacetophenone (139-27-5) + (2,4-dihydroxy-phenyl)-naphthalen-1-yl-methanone → (6-hydroxy-3-naphthalen-1-yl-benzofuran-2-yl)-(3-hydroxy-phenyl)-methanone

Conditions	Yield
Multistep reaction;

3-benzoyloxy-ω-bromoacetophenone (139-27-5) → 1-(3-benzoyloxyphenyl)-2-aminoethanol hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / benzene / 5 h / 20 °C 2: 80 percent / H2 / Pd-black / ethanol / 50 °C View Scheme

3-benzoyloxy-ω-bromoacetophenone (139-27-5) → norfenefrine (536-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaN3; aqueous ethanol 2: palladium/charcoal / Hydrogenation View Scheme

Upstream product

• 139-28-6 3-acetylphenyl benzoate 
• 121-71-1 3-Hydroxyacetophenone 
• 98-88-4 benzoyl chloride 
• 4207-56-1 phenyltrimethylammonium tribromide 

Downstream Products

• 536-21-0 norfenefrine 
• 857561-03-6 2-azido-1-(3-benzoyloxy-phenyl)-ethanone 

Relevant articles and documents

IMIDAZOLE DERIVATIVE

A CB2 receptor modulator comprising an imidazole derivative represented by the general formula (I): [wherein, R1 represents optionally substituted lower alkyl or the like; R2 represents optionally substituted cycloalkyl or the like; R3 represents optionally substituted aryl or the like; and n represents an integer of 0 to 3] or a pharmaceutically acceptable salt thereof as an active ingredient, and the like are provided.