2374-05-2

Basic information

• Product Name: 4-Bromo-2,6-dimethylphenol
• Synonyms: BROMO(4-)2,6-XYLENOL;4-BROMO-2,6-XYLENOL;4-BROMO-2,6-DIMETHYLPHENOL;AKOS BBB/373;4-bromo-6-xylenol;4-BROMO-2,6-DIMETHYLPHENOL, 99.5+%;4-Brom-2,6-dimethylphenol, 99%;4-Bromo-2,6-dimethylphenol 99%
• CAS NO: 2374-05-2
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.06
• EINECS: 219-153-1
• Product Categories: Aromatic Phenols;Benzene series;Phenol&Thiophenol&Mercaptan;Bromine Compounds;Phenols
• Mol File: 2374-05-2.mol

Chemical Properties

• Melting Point: 74-78 °C(lit.)
• Boiling Point: 195.33°C (rough estimate)
• Flash Point: 106.8°C
• Appearance: white to off-white crystalline powder
• Density: 1.3646 (rough estimate)
• Vapor Pressure: 0.0118mmHg at 25°C
• Refractive Index: 1.5650 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 10.10±0.23(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 1862399
• CAS DataBase Reference: 4-Bromo-2,6-dimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2,6-dimethylphenol(2374-05-2)
• EPA Substance Registry System: 4-Bromo-2,6-dimethylphenol(2374-05-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: ZE6780000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2374-05-2(Hazardous Substances Data)

Usage

Uses

Used in Coatings Industry:
4-Bromo-2,6-dimethylphenol is used as a preservative for coatings to prevent microbial fouling and maintain the quality and longevity of the coatings. Its application helps in controlling microbial attack, ensuring the coatings remain effective and durable.
Used in Paper Mills:
In the paper industry, 4-Bromo-2,6-dimethylphenol serves as a preservative for slurries, protecting them from microbial contamination. This helps in maintaining the efficiency of the paper production process and reducing the risk of microbial-related issues.
Used in Oil Field:
4-Bromo-2,6-dimethylphenol is utilized in the oil field industry as a means to control microbial fouling. Its application helps in preventing the growth of microorganisms that can cause damage to the oil field infrastructure and affect the overall efficiency of the oil extraction process.
Used in Leather Process:
In the leather processing industry, 4-Bromo-2,6-dimethylphenol is used as a preservative to protect the leather from microbial attack during the tanning process. This ensures the quality and durability of the final leather product.
Used in Water Treatment Process:
4-Bromo-2,6-dimethylphenol is also used in the water treatment industry to control microbial fouling and protect water systems from microbial attack. Its application helps in maintaining the cleanliness and safety of the water supply.

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

Upstream product

• 84559-81-9 2,6-dimethyl-4-bromo-2,5-cyclohexadienone 
• 13747-35-8 bis[2-hydroxy-3-methylphenyl]methane 
• 556-96-7 5-bromo-1,3-xylene 
• 87-62-7 2,6-dimethylaniline 
• 576-26-1 2.6-dimethylphenol 
• 2816-57-1 2,6-dimethylcyclohexanone 
• 917-54-4 methyllithium 
• 118-79-6 2,4,6-tribromophenol 
• 3536-97-8 diisopropylmagnesium 
• 95729-56-9 6-acetoxy-4-bromo-2,6-dimethylcyclohexa-2,4-dien-1-one 
• 920-39-8 isopropylmagnesium bromide 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 

Downstream Products

• 14804-38-7 5-bromo-2-methoxy-1,3-dimethylbenzene 
• 129835-85-4 N,N-diethyl-P-(3,5-dimethyl-4-hydroxyphenyl)-phosphonamidic chloride 
• 95729-56-9 6-acetoxy-4-bromo-2,6-dimethylcyclohexa-2,4-dien-1-one 
• 144363-60-0 4-bromo-2,6-dimethyl-6-<(E)-styryl>cyclohexa-2,4-dienone 
• 144363-61-1 4-bromo-6-<(E)-p-methoxystyryl>-2,6-dimethylcyclohexa-2,4-dienone 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 91734-80-4 c-6-hydroxy-2,6-dimethyl-r-2,4-c-5-trinitrocyclohex-3-enone 
• 91734-80-4 t-6-hydroxy-2,6-dimethyl-r-2,4,t-5-trinitrocyclohex-3-enone 
• 104545-99-5 4-bromo-6-hydroxy-2,6-dimethyl-r-2,c-5-dinitrocyclohex-3-enone 
• 104546-00-1 4-bromo-2,6-dimethyl-3-nitrophenol 
• 104545-99-5 4-bromo-2,6-dimethyl-2,5,6-trinitrocyclohex-3-enone 
• 104545-99-5 4-bromo-t-6-hydroxy-2,6-dimethyl-r-2,t-5-dinitrocyclohex-3-enone 
• 4198-90-7 3,5-dimethyl-4-hydroxybenzonitrile 
• 2431-91-6 4-methoxy-2,6-dimethylphenol 

Relevant articles and documents

Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5

The nuclear as well as side-chain bromination of activated aromatic substrates has been achieved in high yields and substantial regioselectivity wiht N-Bromosuccinimide (NBS) over HZSM-5.

Catalytic Activation of Unstrained C(Aryl)-C(Alkyl) Bonds in 2,2′-Methylenediphenols

Catalytic activation of unstrained and nonpolar C-C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained C(aryl)-C(alkyl) bonds in 2,2′-methylenediphenols aided by removable directing groups. Good yields of the monophenol products are obtained with tolerating a wide range of functional groups. In addition, the reaction is scalable, and the catalyst loading can be reduced to as low as 0.5 mol %. Moreover, this method proves to be effective to cleave C(aryl)-C(alkyl) linkages in both models of phenolic resins and commercial novolacs resins. Finally, detailed experimental and computational mechanistic studies show that with C-H activation being a competitive but reversible off-cycle reaction, this transformation goes through a directed C(aryl)-C(alkyl) oxidative addition pathway.

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.

Regioselective monobromination of phenols with KBr and ZnAl–BrO3?–layered double hydroxides

The regioselective mono-bromination of phenols has been successfully developed with KBr and ZnAl–BrO3?–layered double hydroxides (abbreviated as ZnAl–BrO3?–LDHs) as brominating reagents. The para site is much favorable and the ortho site takes the priority if para site is occupied. This reaction featured with excellent regioselectivity, cheap brominating reagents, mild reaction condition, high atom economy, broad substrate scope, and provided an efficient method to synthesize bromophenols.

Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses

Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.

Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system

A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

Oxidative bromination reactions in aqueous media by using Bu4NBr/TFA/H2O2 system

Metal-free oxidative bromination reactions in aqueous media were performed using tetrabutylammonium bromide, trifluoroacetic acid, and hydrogen peroxide under mild conditions. Oxidative bromination reaction of alkenes was found to afford the corresponding vic-bromides. Furthermore, this oxidative bromination system is applicable to the oxidative bromination of alkynes, arenes, and 3,4-dihydronaphthalen-1(2H)-one. A gram-scale bromination reaction was also performed successfully.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

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.