14381-51-2

Basic information

• Product Name: 3-BROMOBENZENE-1,2-DIOL
• Synonyms: 3-BROMOBENZENE-1,2-DIOL;2,3-dihydroxy-broMobenzene;1-Bromo-2,3-dihydroxybenzene
• CAS NO: 14381-51-2
• Molecular Formula: C₆H₅BrO₂
• Molecular Weight: 189.0067
• Mol File: 14381-51-2.mol
• Article Data: 15

Chemical Properties

• Melting Point: 40-41℃
• Boiling Point: 243℃
• Flash Point: 101℃
• Appearance: /
• Density: 1.844
• Vapor Pressure: 0.0216mmHg at 25°C
• Refractive Index: 1.657
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in organic solvents.
• PKA: 8.26±0.10(Predicted)
• CAS DataBase Reference: 3-BROMOBENZENE-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOBENZENE-1,2-DIOL(14381-51-2)
• EPA Substance Registry System: 3-BROMOBENZENE-1,2-DIOL(14381-51-2)

Safety Data

• Hazardous Substances Data: 14381-51-2(Hazardous Substances Data)

Usage

Description

3-Bromobenzene-1,2-diol, also known as 3-Bromocatechol, is an organic compound characterized by its needle-like crystalline structure. It is a brominated derivative of benzene-1,2-diol, which features a bromine atom attached to the third carbon position of the benzene ring, along with two hydroxyl groups at the first and second carbon positions. 3-Bromobenzene-1,2-diol is known for its chemical reactivity and is often utilized as a building block in the synthesis of various pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
3-Bromobenzene-1,2-diol is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Agrochemical Industry:
In the agrochemical industry, 3-Bromobenzene-1,2-diol is employed as an intermediate in the production of various agrochemicals. Its properties make it suitable for the development of compounds that can be used in the agricultural sector for pest control, crop protection, and other related applications.
Chemical Properties:
3-Bromobenzene-1,2-diol is characterized by its needle-like crystalline structure, which is a result of its molecular arrangement and intermolecular forces. This physical form is important for its handling, storage, and use in various applications, as it can influence the compound's solubility, reactivity, and stability.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2241, 1947 DOI: 10.1021/ja01201a514

InChI:InChI=1/C6H5BrO2/c7-4-2-1-3-5(8)6(4)9/h1-3,8-9H

Upstream product

• 120-80-9 benzene-1,2-diol 
• 2040-89-3 2-bromo-6-fluorophenol 
• 591-20-8 3-Bromophenol 
• 50-00-0 formaldehyd 
• 95-56-7 2-hydroxybromobenzene 
• 108-86-1 bromobenzene 
• 1829-34-1 2-hydroxy-3-bromobenzaldehyde 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 28165-49-3 6-bromoguaiacol 
• 5424-43-1 3-bromoveratrole 

Downstream Products

• 5424-43-1 3-bromoveratrole 
• 290818-46-1 1,2-diacetoxy-3-bromobenzene 
• 87474-15-5 2,3-dihydro-1,4-benzodioxine-5-sulfonyl chloride 

Relevant articles and documents

One-pot synthesis of substituted catechols from the corresponding phenols

Phenols are converted to salicylaldehydes with paraformaldehyde, MgCl 2-Et3N in THF, and when subsequently treated with aqueous NaOH and H2O2 afford the corresponding catechols. The sequence is conveniently carried out as a one-pot procedure.

Novel preparation process of medical intermediate 3-bromocatechol

The invention discloses a synthesis process of a medical intermediate 3-bromocatechol, which is characterized in that cheap 1,2-dihydroxybenzene (catechol) is used as a raw material, and the 3-bromocatechol is prepared through a one-step substitution reaction. The synthetic route is simple, the production cost is low, and the synthetic process of 3-bromocatechol is suitable for industrial large-scale production.

A new avenue to the Dakin reaction in H2O2-WERSA

We have developed a novel protocol to realize the Dakin reaction in a more greener way. In fact, by the use of H2O2-WERSA, we can oxidize aromatic arylaldehydes to phenols at room temperature. It is remarkable that the catalytic system does not require activation or any toxic ligand, additive/promoter, transition metal catalyst, base, organic solvent and so on. A range of substituted hydroxylated benzaldehydes were screened to investigate the scope of this protocol.

Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols

Biotransformation of 3-substituted and 2,5-disubstituted phenols, using whole cells of P. putida UV4, yielded cyclohexenone cis-diols as single enantiomers; their structures and absolute configurations have been determined by NMR and ECD spectroscopy, X-ray crystallography, and stereochemical correlation involving a four step chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites. An active site model has been proposed, to account for the formation of enantiopure cyclohexenone cis-diols with opposite absolute configurations.