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

• 104-92-7 1-bromo-4-methoxy-benzene 
• 98-88-4 benzoyl chloride 
• 65440-82-6 O-(4-bromophenyl)hydroxylamine 
• 5467-74-3 4-Bromophenylboronic acid 
• 328081-49-8 (p-bromo-N-phenoxy)phthalimide 
• 501-65-5 diphenyl acetylene 
• 108-86-1 bromobenzene 
• 90-02-8 salicylaldehyde 
• 1761-61-1 5-bromosalicyclaldehyde 
• 98-80-6 phenylboronic acid 
• 106-41-2 4-bromo-phenol 
• 591-50-4 iodobenzene 
• 65-85-0 benzoic acid 
• 2476-35-9 5-bromo-2-methoxybenzoic acid 

Downstream Products

• 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 
• 1295567-92-8 C₂₆H₁₉BrN₂O 
• 1295567-93-9 C₂₄H₁₇BrN₂O₂ 
• 1295567-94-0 4-bromo-2-{α-[1-(2-thienyl)benzoimidazol-2-yl]-benzyl}phenol 
• 1295567-95-1 C₂₆H₁₈BrN₃O₃ 
• 180861-07-8 2-[(2-aminophenylimino)phenylmethyl]-4-bromophenol 
• 61810-15-9 2-benzoyloxy-5-bromobenzophenone 
• 1393708-88-7 2-(4-bromobenzoyloxy)-5-bromobenzophenone 

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.

Series of high spin mononuclear iron(III) complexes with Schiff base ligands derived from 2-hydroxybenzophenones

The reaction of various phenols with benzoyl chloride afforded the derivatives of phenyl benzoate that subsequently underwent Fries rearrangement. The obtained 2-hydroxybenzophenone analogues were combined with linear aliphatic triamines, which afforded pentadentate Schiff base ligands. Moreover, nine new iron(iii) complexes with the general formula [Fe(Ln)X] (where, Ln is the dianion of the pentadentate Schiff base ligand, N,N′-bis((2-hydroxy-5-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L1, N,N′-bis((2-hydroxy-3,5-dimethylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L2, N,N′-bis((2-hydroxy-5-chlorophenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L3, N,N′-bis((2-hydroxy-4-methylphenyl)phenyl)methylidene-1,5-diamino-3-azapentane = H2L4, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-azaheptane = H2L5, N,N′-bis((2-hydroxy-5-bromophenyl)phenyl)methylidene-1,7-diamino-4-methyl-4-azaheptane = H2L6 and X is the chlorido, azido or isocyanato terminal ligand) were synthesized and characterized via elemental analysis, and IR and UV-VIS spectroscopy; in addition, the crystal structures of all the complexes were determined by X-ray diffraction. Magnetic investigation reveals high spin state behaviour in all the reported compounds. DFT calculations and analysis of the magnetic functions allowed to extract absolute values of the zero field splitting parameters and exchange coupling constants.

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.