14847-51-9

Basic information

• Product Name: 2-bromo-5-methyl-phenol
• Synonyms: 2-bromo-5-methyl-phenol;Nsc21719;Phenol, 2-bromo-5-methyl-
• CAS NO: 14847-51-9
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.04
• Mol File: 14847-51-9.mol

Chemical Properties

• Melting Point: 38.8°C
• Boiling Point: 209°C (rough estimate)
• Flash Point: 85.8 °C
• Appearance: /
• Density: 1.3839 (rough estimate)
• Vapor Pressure: 0.0863mmHg at 25°C
• Refractive Index: 1.5772 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 8.54±0.10(Predicted)
• CAS DataBase Reference: 2-bromo-5-methyl-phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-5-methyl-phenol(14847-51-9)
• EPA Substance Registry System: 2-bromo-5-methyl-phenol(14847-51-9)

Safety Data

• Hazardous Substances Data: 14847-51-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Production:
2-bromo-5-methyl-phenol is utilized as an intermediate in the synthesis of pharmaceuticals, leveraging its antimicrobial properties to enhance the efficacy of medications.
Used in Dye Manufacturing:
In the dye industry, 2-bromo-5-methyl-phenol serves as a key component in the production of various dyes, contributing to the colorfastness and stability of the final products.
Used as a Disinfectant and Preservative:
Capitalizing on its potent antimicrobial capabilities, 2-bromo-5-methyl-phenol is employed as a disinfectant and preservative in a range of industrial and commercial applications, ensuring the cleanliness and longevity of products.
Used in Organic Compound Synthesis:
As a reagent in chemical reactions, 2-bromo-5-methyl-phenol is instrumental in the synthesis of other organic compounds, broadening its applications across different chemical sectors.
Used in Medicine and Biotechnology:
Owing to its antimicrobial properties, 2-bromo-5-methyl-phenol holds potential in medical and biotechnological fields, where it can be applied in the development of new treatments and technologies to combat microbial infections.

InChI:InChI=1/C7H7BrO/c1-5-2-3-6(8)7(9)4-5/h2-4,9H,1H3

Upstream product

• 53078-85-6 2-bromo-5-methylaniline 
• 2835-98-5 2-Hydroxy-4-methylanilin 
• 108-39-4 3-methyl-phenol 
• 57234-27-2 1-(methoxymethoxy)-3-methylbenzene 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 22356-80-5 2-hydroxy-4-methylbenzenesulfonic acid 
• 591-24-2 3-Methylcyclohexanone 
• 700-38-9 2-nitro-5-methylphenol 

Downstream Products

• 13321-76-1 2,4-dibromo-5-methylphenol 
• 100477-79-0 2,6-Dibrom-3-methylphenol 
• 5415-39-4 6-bromo-2,4-dichloro-3-methyl-phenol 
• 105901-14-2 1-bromo-4-methyl-2-(2-nitrophenoxy)benzene 
• 106037-54-1 (2-bromo-5-methyl-phenyl)-(4-methyl-2-nitro-phenyl)-ether 
• 52905-06-3 2-bromo-5-methylphenyl benzenesulfonate 
• 95740-49-1 1-bromo-2-methoxy-4-methylbenzene 
• 73286-62-1 (-)-2-Bromo-5-methylphenyl (Isopinocampheyloxy)methyl Ether 
• 33008-48-9 6-Methyl-2-phenylbenzofuran 
• 799766-12-4 1-bromo-2-(2,2-dimethoxy-ethoxy)-4-methylbenzene 
• 799766-13-5 7-bromo-4-methylbenzofuran 
• 799766-14-6 7-(4-methoxyphenyl)-4-methylbenzofuran 
• 799766-15-7 7-(4-methoxyphenyl)-benzofuran-4-carbaldehyde 
• 799766-16-8 7-(4-hydroxyphenyl)-benzofuran-4-carbaldehyde 

Relevant articles and documents

Selectivity enhancement of aromatic halogenation reactions at the micellar interface: Effect of highly ionic media

Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.

Discovery of 6-aryl-7-alkoxyisoquinoline inhibitors of IκB kinase-β (IKK-β)

The identification and progression of a potent and selective series of isoquinoline inhibitors of IκB kinase-β (IKK-β) are described. Hit-generation chemistry based on IKK-β active-site knowledge yielded a weakly potent but tractable chemotype that was rapidly progressed into a series with robust enzyme and cellular activity and significant selectivity over IKK-α.

A practical highly selective oxybromination of phenols with dioxygen

A simple, low cost and highly selective method for the synthesis of mono-bromophenols from phenol and electron-rich phenolic compounds has been developed. Bromide ions are used as halogenating agents, dioxygen as a final oxidant, and Cu(OAc)2 as a catalyst.

Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists

Novel biphenyl sulfonamide compounds which are combined angiotensin and endothelin receptor antagonists are claimed along with methods of using such compounds in the treatment of conditions such as hypertension and other diseases, as well as pharmaceutica

Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists

Novel biphenyl sulfonamide compounds which are combined angiotensin and endothelin receptor antagonists are claimed along with methods of using such compounds in the treatment of conditions such as hypertension and other diseases, as well as pharmaceutica

Synthesis of substituted 2-bromo phenols using a novel bromination-dehydrobromination reaction

Substituted 2-bromo-phenols can be synthesised by heating substituted cyclohexanones in neat diethyl dibromomalonate at 100°C. We discuss the efficiency of such a procedure and comment on the possible mechanism.

Synthesis of (±) curcuphenol and (±)-β-sesquiphellandrene

Two naturally occurring compounds curcuphenol 1 and β-sesquiphellandrene 2 have been synthesised using lithium tetrachlorocuperate catalysed coupling reaction.

N-Bromosuccinimide as a Regioselective Nuclear Monobrominating Reagent for Phenols and Naphthols

A wide range of substituted phenols and naphthols were regioselectively monobrominated with N-bromosuccinimide, at para position in acetonitrile and at ortho position in carbon disulfide, under mild conditions in good yields. Methylphenols afforded only nuclear bromination products.

4,4-Dibromo-3-methylpyrazol-5-one: New applications for selective monobromination of phenols and oxidation of sulfides to sulfoxides

Dibromopyrazolone 1, a stable, crystalline solid effects para selective monobromination of phenols and aniline substrates under mild conditions. Selective oxidation of sulfides to sulfoxides can also be accomplished by using 1 in high yields.

Total Synthesis of (-)-Aplysin and (-)-Debromoaplysin

The total synthesis of optically active (-)-aplysin (1) and (-)-debromoaplysin (2) employing novel (isopinocampheyloxy)methyl ethers for phenolic hydroxyl protection and diastereomeric resolution is described.A key transformation is the unusual cyclization of the diastereomeric chlorohydrins 12 and 13 in methanolic base to form the enantiomeric tricyclic alcohols (-)-16 and (+)-16 with cleavage of the acetal-linked (isopinocampheyloxy)methyl resolving/protecting group.This transformation was followed by substitution of the tertiary hydroxyl via the derived chloride with a methyl group by Grignard coupling with methylmagnesium bromide.The methyl insertion occurred with retention of configuration and resulted in formation of the natural aplysin system from 12 in just three steps.The conversion of the methylated tricyclic ether 20 to (-)-debromoaplysin (2) was accomplished in two steps by double bond isomerization and selective reduction.Bromination of (-)-2 afforded (-)-aplysin (1).