16434-97-2

Basic information

• Product Name: 5-bromo[1,1'-biphenyl]-2-ol
• Synonyms: 5-bromo[1,1'-biphenyl]-2-ol;4-Bromo-2-phenylphenol;5-Bromobiphenyl-2-ol
• CAS NO: 16434-97-2
• Molecular Formula: C₁₂H₉BrO
• Molecular Weight: 249.10326
• EINECS: 240-490-5
• Mol File: 16434-97-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 53.35°C
• Boiling Point: 273.2°C (rough estimate)
• Flash Point: 151.9°C
• Appearance: /
• Density: 1.4095 (rough estimate)
• Refractive Index: 1.6565 (estimate)
• CAS DataBase Reference: 5-bromo[1,1'-biphenyl]-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo[1,1'-biphenyl]-2-ol(16434-97-2)
• EPA Substance Registry System: 5-bromo[1,1'-biphenyl]-2-ol(16434-97-2)

Safety Data

• Hazardous Substances Data: 16434-97-2(Hazardous Substances Data)

Usage

General Description

5-Bromo[1,1'-biphenyl]-2-ol, also known as 2-bromo-4-hydroxybiphenyl, is a chemical compound with the molecular formula C12H10BrOH. It belongs to the class of biphenyl compounds, which are aromatic hydrocarbons consisting of two benzene rings connected by a single bond. This specific compound is characterized by the presence of a bromine atom and a hydroxyl group attached to the biphenyl structure. It is commonly used as a building block in organic synthesis and pharmaceutical research. Its versatility and unique structural features make it an important intermediate for the production of various pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, its potential applications in medicinal chemistry and drug discovery have made it a subject of interest for further research and development.

Upstream product

• 57018-28-7 acetic acid-(5-bromo-biphenyl-2-yl ester) 
• 90-43-7 2-Phenylphenol 
• 75-15-0 carbon disulfide 
• 7726-95-6 bromine 
• 3271-80-5 2-acetoxybiphenyl 
• 40925-68-6 2-amino-4-bromo-phenol 
• 5747-23-9 2-phenyl-1,3,2-benzodioxaborole 

Downstream Products

• 57018-28-7 acetic acid-(5-bromo-biphenyl-2-yl ester) 

Relevant articles and documents

Transition-Metal-Free C(sp2)–C(sp2) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters

A transition-metal-free C(sp2)?C(sp2) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and density functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism.

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.