15191-36-3

Basic information

• Product Name: 2-BROMO-4,6-DIMETHYLBENZENOL
• Synonyms: 2-BROMO-4,6-DIMETHYLBENZENOL;2-Bromo-4,6-dimethylphenol 96%;6-Bromo-2,4-xylenol, 5-Bromo-4-hydroxy-m-xylene;2-Bromo-4,6-dimethylphenol96%
• CAS NO: 15191-36-3
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.06
• Mol File: 15191-36-3.mol

Chemical Properties

• Boiling Point: 229.4°Cat760mmHg
• Flash Point: 92.5°C
• Appearance: /
• Density: 1.471g/cm³
• Vapor Pressure: 0.0462mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-BROMO-4,6-DIMETHYLBENZENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-4,6-DIMETHYLBENZENOL(15191-36-3)
• EPA Substance Registry System: 2-BROMO-4,6-DIMETHYLBENZENOL(15191-36-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 15191-36-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4,6-dimethylbenzenol is used as an intermediate in the synthesis of pharmaceuticals for its unique reactivity and properties, contributing to the development of new drugs and medications.
Used in Dye and Fragrance Industry:
2-BROMO-4,6-DIMETHYLBENZENOL is utilized as an intermediate in the production of dyes and fragrances, where its chemical structure plays a crucial role in imparting color and scent to various products.
Used in Disinfectants and Antiseptics:
2-Bromo-4,6-dimethylbenzenol is used as an active ingredient in disinfectants and antiseptics due to its antifungal and antibacterial properties, helping to prevent the spread of infections and maintain hygiene.
It is important to handle 2-bromo-4,6-dimethylbenzenol with care, as it can be harmful if ingested or inhaled, and can cause skin irritation upon contact. Despite these precautions, its diverse applications in the chemical and pharmaceutical industries highlight its significance in the development of various products.

InChI:InChI=1/C8H9BrO/c1-5-3-6(2)8(10)7(9)4-5/h3-4,10H,1-2H3

Upstream product

• 41825-73-4 2-bromo-4,6-dimethylaniline 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 917-54-4 methyllithium 
• 7726-95-6 bromine 
• 105-67-9 2,4-Xylenol 
• 51770-93-5 4-hydroxy-2,4-dimethyl-2,5-cyclohexadienone 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 83755-88-8 4,6-dibromo-2,4-dimethyl-cyclohexa-2,5-dienone 
• 556-96-7 5-bromo-1,3-xylene 
• 67-56-1 methanol 
• 859819-97-9 2-bromo-4-(2,6-dibromo-4-methyl-anilino)-4,6-dimethyl-cyclohexa-2,5-dienone 
• 90841-66-0 6-acetoxy-2-bromo-4,6-dimethylcyclohexa-2,4-dien-1-one 

Downstream Products

• 83755-88-8 4,6-dibromo-2,4-dimethyl-cyclohexa-2,5-dienone 
• 83755-92-4 3,5,6-tribromo-2,4-dimethylphenol 
• 65492-45-7 1-bromo-2-methoxy-3,5-dimethylbenzene 
• 90841-66-0 6-acetoxy-2-bromo-4,6-dimethylcyclohexa-2,4-dien-1-one 
• 2785-75-3 3,5-dimethylcatechol 
• 83755-93-5 6-bromo-2,4-bis(bromomethyl)phenol 
• 95717-62-7 2-bromo-2,6-dimethylphenyl isopropyl ether 
• 769923-11-7 6-(2'-bromo-4'-methoxyphenoxymethyl)-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 909697-46-7 4-(2-bromo-4,6-dimethyl-phenoxymethyl)-1-methyl-1H-quinolin-2-one 
• 103529-11-9 3-bromo-4-hydroxy-5-methylbenzaldehyde 
• 1572185-05-7 methyl 2-(2-(furan-2-yl)-4,6-dimethylphenoxy)acetate 
• 1572185-06-8 2-(2-(furan-2-yl)-4,6-dimethylphenoxy)acetohydrazide 
• 1572184-42-9 (E)-N’-((1H-indol-4-yl)methylene)-2-(2-(furan-2-yl)-4,6-dimethylphenoxy)acetohydrazide 
• 1572184-44-1 C₂₃H₂₁N₃O₃ 

Relevant articles and documents

Selective Bromination of β-Positions of Porphyrin by Self-Catalytic Behaviour of VOTPP: Facile Synthesis, Electrochemical Redox Properties and Catalytic Application

Oxidovanadium(IV) complex of β-octabromo-meso-tetraphenylporphyrin, {[VIVO(TPPBr8)], 2} was synthesized by self-catalytic oxidative bromination of meso-tetraphenylporphyrinatooxidovanadium(IV) {[VIVO(TPP), 1} in excellent yield under mild conditions at 25 °C and its structure was confirmed by single crystal X-ray study. UV-Vis and 1H NMR spectra further confirmed that the meso-phenyl rings are not brominated and thus emphasizes on the selectivity as well as synthetic importance of this catalytic method. In the presence of substrates e. g. phenol derivatives, 1 biomimics the vanadium bromoperoxidase (VBPO) enzyme and catalyses the oxidative bromination of substrates in water at 25 °C. Remarkably, 2 also catalyses the oxidative bromination of phenol derivatives under similar reaction conditions with very high turnover frequency (TOF) values (ca. 29 s?1) along with its recyclability. It was found that 2 showed superior catalytic performance as compared to 1 because of its electron deficient nature due to electron withdrawing bromo substituents and robust saddle shaped nonplanar structure (further supported by DFT studies).

New procedure for the highly regioselective aerobic bromination of aromatic compounds using copper-based nanocatalyst

A new procedure for the highly regioselective aerobic bromination of aromatic compounds in the presence of copper-based nanoparticles (CuO/ZnO nanocatalyst) under reflux condition is described. Mechanistic parameters are discussed and the plausible mechanism is proposed. Recyclability of the CuO/ZnO nanocatalyst has also been explored upon aerobic bromination of aromatic compounds.

Visible-Light-Induced Intramolecular C(sp2)-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination ? electron deficient olefin aziridination ≈ C(sp2)-H amination ? C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism

Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.

Green, mild and efficient bromination of aromatic compounds by HBr promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane in water as a solvent

A combination of HBr and trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as a new and powerful oxidant was found effective for facile bromination of different aromatic compounds at room temperature in water as a green solvent. Mild reaction conditions, high selectivity and yield, high reaction rate and non-toxicity are some of the major advantages of this synthetic protocol.

Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane

Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.

A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions

Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide as a regenerable and useful reagent for bromination of phenols under mild conditions

1-Benzyl-4-aza-1-azoniabicyclo[2.2.2]octane tribromide has been examined over several phenolic compounds under mild conditions. The reaction gives brominated phenols in good to excellent yields. Straightforward work-up of the reaction yields pure products in several cases.

Intramolecular carbolithiation of allyl o-lithioaryl ethers: A new enantioselective synthesis of functionalized 2,3-dihydrobenzofurans

A new and easy method for the diastereoselective synthesis of 3-functionalized 2,3-dihydrobenzofuran derivatives from allyl 2-bromoaryl ethers is described. The key step of this transformation involves an intramolecular carbolithiation reaction of allyl 2-lithioaryl ethers. The substituents in both the allyl and the aryl moieties play an important and decisive role in stopping the reaction at the benzofuran thus avoiding a γ-elimination reaction. Finally, this process is amenable to the synthesis of enantiomerically enriched compounds by using ( - )-sparteine as a chiral inductor.