609-22-3

Usage

Uses

Used in Industrial and Agricultural Applications:
4,6-DIBROMO-O-CRESOL is used as a disinfectant and pesticide for its ability to control microbial growth, ensuring cleanliness and preventing contamination in industrial processes and agricultural settings.
Used in Personal Care Products and Cosmetics:
In the personal care and cosmetics industry, 4,6-DIBROMO-O-CRESOL serves as a preservative to prevent the spoilage of products by inhibiting the growth of bacteria and fungi, thereby extending the shelf life and maintaining the quality of these products.
However, due to its potential harmful effects, including skin and eye irritation, as well as possible adverse impacts on the respiratory and nervous systems, it is crucial to handle 4,6-DIBROMO-O-CRESOL with proper safety measures and precautions.

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

Upstream product

• 2467-25-6 bis(4-hydroxy-3-methylphenyl)methane 
• 95-48-7 ortho-cresol 
• 90721-59-8 6-acetoxy-2,4-dibromo-6-methylcyclohexa-2,4-dien-1-one 
• 920-39-8 isopropylmagnesium bromide 
• 3536-97-8 diisopropylmagnesium 
• 77339-18-5 4,4,6-tribromo-2-methylcyclohexa-2,5-dienone 
• 83755-95-7 4,6-dibromo-4-t-butyl-2-methylcyclohexa-2,5-dienone 
• 917-54-4 methyllithium 
• 118-79-6 2,4,6-tribromophenol 
• 74-88-4 methyl iodide 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 56-23-5 tetrachloromethane 
• 67-66-3 chloroform 

Downstream Products

• 20294-50-2 4-bromo-2-methyl-6-nitrophenol 
• 4186-54-3 2-(bromomethyl)-4,6-dibromophenol 
• 6293-55-6 2-bromo-6-methyl-[1,4]benzoquinone 
• 534-52-1 6-methyl-2,4-dinitrophenol 
• 4186-49-6 2-bromo-6-methyl-4-nitrophenol 
• 86030-85-5 acetic acid-(2,4-dibromo-6-methyl-phenyl ester) 
• 7463-93-6 2,4-dibromo-6-methyl-anisole 
• 90721-59-8 6-acetoxy-2,4-dibromo-6-methylcyclohexa-2,4-dien-1-one 
• 52040-87-6 2-(2,4-Dibrom-6-methylphenoxy)-5-nitrobenzoesaeuremethylester 
• 52040-68-3 2-(2,4-Dibromo-6-methyl-phenoxy)-3,5-dinitro-benzoic acid methyl ester 
• 52118-95-3 4-(2,4-Dibrom-6-methylphenoxy)-3,5-dinitrobenzoesaeuremethylester 
• 125318-21-0 (E)-3-(4-chloro-3-methyl-2-butenyl)-2,5-bis(methoxymethoxy)toluene 
• 50848-61-8 1-bromo-2,5-bis(methoxymethoxy)-3-methylbenzene 
• 125318-29-8 3-allyl-2,5-bis(methoxymethoxy)toluene 

Relevant academic research and scientific papers

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.

Method for photocatalytic synthesis of polybrominated phenol compound in water phase

The invention discloses a method for photocatalytic synthesis of a polybrominated phenol compound in a water phase, comprising the following steps: adding a catalytic amount of a radical initiator, aphenol derivative and low-toxic and cheap bromide salt and water into a reaction vessel, reacting at room temperature at 5 W power in a photocatalytic reactor for a certain period, extracting with ethyl acetate and then re-crystallizing to obtain a polybrominated phenol compound. The above radical initiator is eosin, azobisisobutanol, sodium persulfate, ammonium persulfate or potassium persulfate.The free radical initiator and the bromine salt are cheap and easily available, and the method is an ideal synthesis method of the polybrominated phenol compound. According to the method, low-toxicity bromine salt instead of liquid bromine is used to carry out a bromination reaction, unstable and explosive hydrogen peroxide is replaced with the cheap and easily-available free radical initiator, and an emerging photocatalytic method is used. The polybrominated phenol compound can be obtained in a high yield by only using a 5W power lamp for the reaction, the reaction selectivity is high, by-products are less, and the post-treatment is simple.

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.

Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide

Regioselective monobromination of various aromatics was achieved at room temperature using N-bromosuccinimide and 5 mol% of thioamides in acetonitrile. With thiourea as catalyst, activated aromatics, such as anisole, acetanilide, benzamide and phenol analogues containing electron donating or withdrawing groups, were brominated with high regioselectivity. Room temperature brominations of weakly activated aromatics and deactivated 9-fluorenone were accomplished by 5 mol% thioacetamide, higher substrates concentrations and longer reaction times. A backbonding of the bromine lone pairs with the π*of C[dbnd]S group and a halogen bond between the halogen bond donor bromine and the halogen bond acceptor sulfur of the thioamide are thought to be the principal interactions and cause of N-bromosuccinimide activation.

Vanadium bromoperoxidase (VBrPO) mimics: Synthesis, structure and a comparative account of the catalytic activity of newly synthesized oxidovanadium and oxido-peroxidovanadium complexes

The bioinspired catalytic activities of two newly synthesised vanadium(iv)dioxido (complex 1) and vanadium(v) oxido-peroxido (complex 2) complexes with the neutral tridentate benzimidazole ligand, 2,6-di-(1H-benzo[d]imidazol-2-yl)pyridine (Byim) have been established. The bromoperoxidase activities of these complexes have been established through the activation of C-H bonds of substrates like phenol, o-cresol and p-cresol. The products, characterized by GC analysis shows that good conversions have been achieved. Considering the catalytic efficiency of the complexes, complex 2, with one in-built peroxido group is found to be more potent than complex 1. The catalytic cycles of both the complexes have been established from experimental results.

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.

Preparation of carbazole and dibenzofuran derivatives by selective bromination on aromatic rings or benzylic groups with N-bromosuccinimide

N-Bromosuccinimide (NBS), a bromine source, has been used to study the bromination of toluidine and cresols systematically to clarify the underlying mechanism and the orientation effect. It has been found that bromination of toluidine and cresols which possess electron-donating NH2/OH with NBS gives electrophilic aromatic substitution products quickly instead of the desired benzylic bromination products. In contrast, when the electronic effect of the substituted groups is reversed, only the benzylic bromination products are gained. Based on this methodology, several potential AChE inhibitors, such as 2-methoxy-5-(benzylamino)methyl-dibenzofuran, 3-bromo-2-methoxy-5-methyl-9H- carbazole, 3,6-dibromo-2-methoxy-5-methyl-9H-carbazole, and 5-(bromomethyl)-2- methoxy-9H-(phenylsulfonyl)-carbazole have been synthesized.

Synthesis, structural characterization, VHPO mimicking peroxidative bromination and DNA nuclease activity of oxovanadium(v) complexes

The two novel oxovanadium(v) complexes [VO(PyDC)(BHA)] (1) [PyDC = pyridine-2,6-dicarboxylate, BHA = benzohydroxamate] and [VO(PyDC)(BPHA)] (2) [BPHA = benzophenyl hydroxamate] were synthesized by successive addition of a methanolic solution of H2PyDC and the corresponding hydroxamic acid ligand to the aqueous solution of ammonium metavanadate (NH4VO 3). The hydroxamic acid ligands were characterized by elemental analysis, IR, UV-vis and NMR studies whereas the complexes were characterized by IR, UV-vis, CHN, molar conductance, magnetic moment, mass and NMR spectroscopic methods. The structures of the complexes were determined by single crystal X-ray crystallography. The structures of both complexes reveal that vanadium(v) has distorted octahedral geometry. The bromoperoxidase activities of these complexes have been demonstrated through the activation of C-H bonds of phenol, o-cresol and p-cresol. The catalytic products have been characterized by GC-MS analysis which shows that good conversions have been achieved. So far as the catalytic efficiency of the complexes are concerned complex 2 is found to be superior to complex 1. Both the complexes were tested for DNA nuclease activity with pUC19 plasmid DNA. The results show that both of them exhibited nuclease activity against pUC19 circular plasmid DNA. The complexes produced both nicked coils and linear forms. In this case also it is observed that complex 2 shows better nuclease activity than complex 1.

Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles

Bromoperoxidases from the brown alga Ascophyllum nodosum, abbreviated as VBrPO(AnI) and VBrPO(AnII), show 41% sequence homology and differ by a factor of two in the percentage of α-helical secondary structures. Protein monomers organize into homodimers for VBrPO(AnI) and hexamers for VBrPO(AnII). Bromoperoxidase II binds hydrogen peroxide and bromide by approximately one order of magnitude stronger than VBrPO(AnI). In oxidation catalysis, bromoperoxidases I and II turn over hydrogen peroxide and bromide similarly fast, yielding in morpholine-4-ethanesulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon-bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with larger energy gaps between the π-type HOMO of, for example, an alkene and the σ*Br,X-type LUMO of the bromination reagent. By using this approach, the reactivity of substrates and selectivity for carbon-bromine bond formation in reactions mediated by vanadate-dependent bromoperoxidases become predictable, as exemplified by the synthesis of bromopyrroles occurring naturally in marine sponges of the genera Agelas, Acanthella, and Axinella. The Royal Society of Chemistry.

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes

A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.