591-20-8 Usage
Description
3-Bromophenol is an organic compound with the chemical formula C6H4BrOH, featuring a bromine atom attached to a phenol group. It is a low-melting pale yellow semi-solid that is soluble in ether, ethanol, and chloroform. 3-Bromophenol is known for its role as an enzyme inhibitor and serves as a crucial intermediate in various chemical syntheses.
Uses
Used in Pharmaceutical Industry:
3-Bromophenol is used as an intermediate for the synthesis of various pharmaceuticals, including the anticancer analgesic tramadol. It plays a significant role in the production of triarylmethane thiophene anti-tuberculosis drugs and 4-aryl piperidine antipruritic drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Bromophenol is utilized as an intermediate in the development of various agrochemicals, contributing to the creation of products that help protect crops and enhance agricultural productivity.
Used in Dye Industry:
3-Bromophenol is also employed as an intermediate in the manufacture of dyestuff, where it contributes to the production of a range of dyes used in different industries, including textiles and plastics.
Used in Organic Synthesis:
3-Bromophenol acts as an enzyme inhibitor and is used in the preparation of 3-bromophenyl ester by reacting with benzoyl chloride in the presence of triethylamine as a catalyst. This reaction is an essential step in organic synthesis, where 3-bromophenol serves as a key building block for the creation of more complex molecules.
Additionally, 3-Bromophenol is an intermediate of organic synthesis and can be used to synthesize 3-bromoanisole, further expanding its applications in the chemical industry.
Preparation
3-bromophenol is synthesized by diazotization and bromination of 3-aminophenol. Dissolve 3-aminophenol in sulfuric acid, cool to below 10°C, and add aqueous sodium nitrite dropwise. After the diazotization reaction, the filtrate is filtered and hydrolyzed with cuprous bromide. Then distillation, collect the evaporated liquid with table salt and filter, the filtrate is extracted with ether, the extract is dried, distilled to recover the ether, and then distilled 3-bromophenol.
Check Digit Verification of cas no
The CAS Registry Mumber 591-20-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 591-20:
(5*5)+(4*9)+(3*1)+(2*2)+(1*0)=68
68 % 10 = 8
So 591-20-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H5BrO/c7-5-2-1-3-6(8)4-5/h1-4,8H
591-20-8Relevant articles and documents
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Koelsch
, p. 969 (1939)
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Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information, p. 3925 - 3931 (2021/08/24)
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
Synthesis of Polysubstituted Meta-Halophenols by Anion-Accelerated 2π-Electrocyclic Ring Opening
Staudt, Markus,S?lling, Theis,Bunch, Lennart
supporting information, p. 10941 - 10947 (2021/06/16)
Disrotatory – thermally allowed – 2π-electrocyclic ring-opening reactions require high temperatures to proceed. Herein, we report the first anion-accelerated 2π-electrocyclic ring opening of 6,6-dihalobicyclo[3.1.0]hexan-2-ones at low temperature to give the corresponding meta-halophenols in good to high yields (18 examples, 29–92 % yield, average: 65 %). Many of the phenols have unconventional substitution patterns and are reported here for the first time. Furthermore, the strength of the methodology was shown by the total synthesis of the densely functionalized phenolic natural product caramboxin (isolated as the lactam dehydrate). The reaction mechanism underlying the anion-acceleration was investigated in an ab initio study, which concluded that base-mediated proton abstraction anti to the concurrently departing endo-bromine was the initiating step in an overall concerted reaction mechanism leading directly to the meta-halophenol.
