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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Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization
Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana
supporting information, p. 1629 - 1632 (2021/02/09)
This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.
Highly efficient, recyclable and alternative method of synthesizing phenols from phenylboronic acids using non-endangered metal: Samarium oxide
Yusoff, Hanis Mohd,Bala Chandran, Prasana Devi,Sayuti, Fatin Amira Binti,Kan, Su-Yin,Mohd Radzi, Siti Aisha,Yong, Fu-Siong Julius,Lee, Oon Jew,Chia, Poh Wai
, (2021/06/25)
Oxidation of phenylboronic acid to phenol is one of the important industrial processes and it is generally employed in the plastic, explosive and drug manufacturing industries. Over the past decades, numerous efficient methods have been described for the generation of phenols from phenylboronic acids in the presence of oxidant. However, these methods suffered from various limitations, including the use of expensive, toxic reagents and sophisticated protocol to synthesise the phenols. Additionally, some of these reported literatures employed endangered metals, in which mankind is facing the risk of limited supply of these elements in 20 years’ time from now. As such, a viable alternative and green method for achieving organic synthesis is highly sought after by the chemists of today. Herein, we report for the first time a facile, efficient and alternative method in the preparation of phenols from phenylboronic acids using non-endangered metal as catalyst. In all cases, all phenols were afforded in satisfactory yields (81–96%) by employing column-free method. In the recyclability study, the Sm2O3 catalyst was found to possess good catalytic performance, even after being reused for five consecutive times (96–91%). In addition, SEM result revealed that the morphology of the recycled Sm2O3 catalyst was well preserved after five successive uses, which indicate no observable changes occurred in the recovered catalysts. As a final note, the current method is anticipated to be useful for industries manufacturing chemical intermediates as it provides an alternative method of catalysis by using a non-endangered metal in organic transformations.
