55082-33-2

Basic information

• Product Name: 5-BROMO-2-HYDROXYBENZOPHENONE
• Synonyms: NSC22344;(5-BROMO-2-HYDROXYPHENYL)(PHENYL)METHANONE;5-BROMO-2-HYDROXYBENZOPHENONE
• CAS NO: 55082-33-2
• Molecular Formula: C₁₃H₉BrO₂
• Molecular Weight: 277.11
• Product Categories: C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 55082-33-2.mol
• Article Data: 18

Chemical Properties

• Melting Point: 111-114 °C(lit.)
• Boiling Point: 365.5°C at 760 mmHg
• Flash Point: 174.9°C
• Appearance: /
• Density: 1.521g/cm³
• Vapor Pressure: 7.41E-06mmHg at 25°C
• Refractive Index: 1.639
• PKA: 7.37±0.43(Predicted)
• CAS DataBase Reference: 5-BROMO-2-HYDROXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-HYDROXYBENZOPHENONE(55082-33-2)
• EPA Substance Registry System: 5-BROMO-2-HYDROXYBENZOPHENONE(55082-33-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 55082-33-2(Hazardous Substances Data)

Usage

Preparation

Preparation by Fries rearrangement of p-bromophenyl benzoate with aluminium chloride without solvent at 150° for 15 min (42%).

InChI:InChI=1/C13H9BrO2/c14-10-6-7-12(15)11(8-10)13(16)9-4-2-1-3-5-9/h1-8,15H

Upstream product

• 1523-17-7 4-bromophenyl benzoate 
• 117-99-7 2-Hydroxybenzophenone 
• 106-41-2 4-bromo-phenol 
• 98-07-7 Benzotrichlorid 
• 615-58-7 2,4-dibromophenol 
• 100-47-0 benzonitrile 
• 2476-35-9 5-bromo-2-methoxybenzoic acid 
• 65-85-0 benzoic acid 
• 591-50-4 iodobenzene 
• 1761-61-1 5-bromosalicyclaldehyde 
• 108-86-1 bromobenzene 
• 98-88-4 benzoyl chloride 
• 98-80-6 phenylboronic acid 
• 90-02-8 salicylaldehyde 

Downstream Products

• 69918-18-9 (E)-(5-bromo-2-hydroxyphenyl)(phenyl)methanone oxime 
• 84437-30-9 3-benzoyl-4-hydroxybenzonitrile 
• 84437-31-0 2-benzoyl-4-methoxyiminomethylphenol hydrochloride 
• 84437-32-1 4-Hydroxy-3-(imino-phenyl-methyl)-benzamidine 
• 84437-28-5 4-amidino-2-benzoylphenol 
• 84437-25-2 4-amidino-2-benzoylphenyl benzoate 
• 80532-08-7 4-amidino-2-benzoylphenyl 4-guanidinobenzoate 
• 4294-89-7 5-bromo-2-hydroxy-N-phenylbenzamide 
• 69918-18-9 5-bromo-2-hydroxy-benzophenone-(Z)-oxime 
• 847347-56-2 3-{4-[3-(2-benzoyl-4-bromo-phenoxy)-butoxy]-2-methyl-phenyl}-propionic acid methyl ester 
• 324061-77-0 4-bromo-2-(hydroxy(phenyl)methyl)phenol 
• 1225592-31-3 (2-benzoyl-4-bromophenoxy)acetonitrile 
• 1295567-90-6 4-bromo-2-{α-[1-(4-bromophenyl)benzoimidazol-2-yl]benzyl}phenol 
• 1295567-91-7 4-bromo-2-{α-[1-(4-dimethylaminophenyl)benzoimidazol-2-yl]benzyl}phenol 

Relevant articles and documents

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

Acid-Functionalised Magnetic Ionic Liquid [AcMIm]FeCl4 as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

An acid-functionalised, magnetic, room-temperature ionic liquid, 1-acyl-3-methylimidazolium tetrachloroferrate ([AcMIm]FeCl4), was synthesised and its optical, magnetic, and thermal properties were investigated. The magnetic moment (0.05402 emu in 2 T magnetic fields) showed strong paramagnetic behaviour, and thermogravimetric analysis indicated very good thermal stability with a decomposition temperature higher than 230 °C. Additionally, [AcMIm]FeCl4 efficiently catalysed the oxidative ipso-hydroxylation of arylboronic acids and regioselective Friedel–Crafts acylation without external organic solvent or additives, such as acids, base, and ligands. This functionalised ionic liquid, [AcMIm]FeCl4, was recycled and reused at least six times without significant loss of its catalytic properties and stability.

Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage

A Rh-Cu bimetallic catalyzed o-acylation of acyloxacetamide with alkynes has been described. This transformation provides a novel, concise way to synthesize ortho-acylphenols using functionalized alkynes as acylating reagents. Mechanistic studies revealed a Rh-Cu relay process, in which O2 plays a critical role for the formation of carbonyl compounds.