609-22-3

Basic information

• Product Name: 4,6-DIBROMO-O-CRESOL
• Synonyms: AKOS BBB/370;4,6-DIBROMO-O-CRESOL;4,6-Dibromo-o-methylphenol
• CAS NO: 609-22-3
• Molecular Formula: C₇H₆Br₂O
• Molecular Weight: 265.93
• Mol File: 609-22-3.mol
• Article Data: 34

Chemical Properties

• Melting Point: 58°C
• Boiling Point: 259°C at 760 mmHg
• Flash Point: 110.4°C
• Appearance: /
• Density: 1.8014 (rough estimate)
• Vapor Pressure: 0.00822mmHg at 25°C
• Refractive Index: 1.5030 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.22±0.23(Predicted)
• CAS DataBase Reference: 4,6-DIBROMO-O-CRESOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIBROMO-O-CRESOL(609-22-3)
• EPA Substance Registry System: 4,6-DIBROMO-O-CRESOL(609-22-3)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 609-22-3(Hazardous Substances Data)

Usage

General Description

4,6-DIBROMO-O-CRESOL is a chemical compound that belongs to the class of brominated phenolic compounds. It is commonly used as a disinfectant and pesticide due to its antimicrobial properties. With its strong bactericidal and fungicidal properties, 4,6-DIBROMO-O-CRESOL is used in various industrial and agricultural applications to control and prevent the growth of microorganisms. It is also utilized as a preservative in personal care products and cosmetics. However, exposure to 4,6-DIBROMO-O-CRESOL can be harmful, causing skin and eye irritation, as well as adverse effects on the respiratory and nervous systems. Therefore, proper handling and safety precautions are necessary when working with this chemical.

InChI:InChI=1/C7H6Br2O/c1-4-2-5(8)3-6(9)7(4)10/h2-3,10H,1H3

Upstream product

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Downstream Products

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• 6293-55-6 2-bromo-6-methyl-[1,4]benzoquinone 
• 4186-54-3 2-(bromomethyl)-4,6-dibromophenol 
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• 1402041-27-3 3-(4-bromobenzyl)-2,6-dimethylnaphthalene-1,4-dione 
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Relevant articles and documents

A scalable and green one-minute synthesis of substituted phenols

A mild, green and highly efficient protocol was developed for the synthesis of substituted phenols via ipso-hydroxylation of arylboronic acids in ethanol. The method utilizes the combination of aqueous hydrogen peroxide as the oxidant and H2O2/HBr as the reagent under unprecedentedly simple and convenient conditions. A wide range of arylboronic acids were smoothly transformed into substituted phenols in very good to excellent yields without chromatographic purification. The reaction is scalable up to at least 5 grams at room temperature with one-minute reaction time and can be combined in a one-pot sequence with bromination and Pd-catalyzed cross-coupling to generate more diverse, highly substituted phenols.

Synthesis and antitumor activity evaluation of compounds based on toluquinol

Encouraged by the promising antitumoral, antiangiogenic, and antilymphangiogenic properties of toluquinol, a set of analogues of this natural product of marine origin was synthesized to explore and evaluate the effects of structural modifications on their cytotoxic activity. We decided to investigate the effects of the substitution of the methyl group by other groups, the introduction of a second substituent, the relative position of the substituents, and the oxidation state. A set of analogues of 2-substituted, 2,3-disubstituted, and 2,6-disubstituted derived from hydroquinone were synthesized. The results revealed that the cytotoxic activity of this family of compounds could rely on the hydroquinone/benzoquinone part of the molecule, whereas the substituents might modulate the interaction of the molecule with their targets, changing either its activity or its selectivity. The methyl group is relevant for the cytotoxicity of toluquinol, since its replacement by other groups resulted in a significant loss of activity, and in general the introduction of a second substituent, preferentially in the para position with respect to the methyl group, was well tolerated. These findings provide guidance for the design of new toluquinol analogues with potentially better pharmacological properties.

A quick, mild and efficient bromination using a CFBSA/KBr system

Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.