16434-97-2

Usage

Uses

Used in Pharmaceutical Research:
5-Bromo[1,1'-biphenyl]-2-ol is used as a building block in pharmaceutical research for the development of various pharmaceuticals. Its unique structure and functional groups make it a promising candidate for the synthesis of new drugs with potential therapeutic applications.
Used in Agrochemicals:
In the agrochemical industry, 5-bromo[1,1'-biphenyl]-2-ol is used as an intermediate for the production of various agrochemicals. Its structural features contribute to the development of effective compounds for pest control and crop protection.
Used in Fine Chemicals Production:
5-Bromo[1,1'-biphenyl]-2-ol is utilized as an important intermediate in the synthesis of fine chemicals. Its unique properties allow for the creation of high-quality specialty chemicals used in various industries, such as fragrances, dyes, and coatings.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-bromo[1,1'-biphenyl]-2-ol is employed as a key intermediate for the synthesis of novel compounds with potential therapeutic properties. Its structural features enable the development of new drugs targeting various diseases and medical conditions.
Used in Drug Discovery:
5-Bromo[1,1'-biphenyl]-2-ol is a subject of interest in drug discovery due to its potential applications in the development of new pharmaceuticals. Its unique structural features and versatility make it a valuable compound for exploring new drug candidates and advancing the field of medicinal chemistry.

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 
• 5747-23-9 2-phenyl-1,3,2-benzodioxaborole 
• 40925-68-6 2-amino-4-bromo-phenol 
• 3271-80-5 2-acetoxybiphenyl 

Downstream Products

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

Relevant academic research and scientific papers

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.

Regioselective bromination of arenes mediated by triphosgene-oxidized bromide

This article first time describes triphosgene (BTC) as an oxidant while the non-toxic and easy-to-handle potassium bromide (KBr) as the source of bromine to the bromination reaction of aromatic substrates. The novel brominating protocol gives excellent para-regioselectivity of the alkoxyl/hydroxyl arenes and high yield, offering good potential of commercial scale applications. The mechanism of “Triphosgene oxidize bromide” was proposed.

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.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

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.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.