22802-40-0

Basic information

• Product Name: 2,6-dibromo-3,4-xylenol
• Synonyms: 2,6-dibromo-3,4-xylenol;2,6-Dibromo-3,4-dimethylphenol;3,4-Dimethyl-2,6-dibromophenol
• CAS NO: 22802-40-0
• Molecular Formula: C₈H₈Br₂O
• Molecular Weight: 279.95652
• EINECS: 245-229-9
• Mol File: 22802-40-0.mol

Chemical Properties

• Boiling Point: 265°Cat760mmHg
• Flash Point: 114°C
• Appearance: /
• Density: 1.832g/cm³
• Vapor Pressure: 0.00575mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 2,6-dibromo-3,4-xylenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dibromo-3,4-xylenol(22802-40-0)
• EPA Substance Registry System: 2,6-dibromo-3,4-xylenol(22802-40-0)

Safety Data

• Hazardous Substances Data: 22802-40-0(Hazardous Substances Data)

Usage

Specific content

A chemical compound with two bromine atoms attached to a xylenol molecule.

Specific content

Used in personal care and pharmaceutical products to control the growth of microorganisms.

Specific content

Effective in inhibiting the growth of bacteria and fungi, making it suitable for various applications.

Specific content

Included in industrial and household products to maintain cleanliness and prevent contamination.

Specific content

Incorporated into a wide range of consumer products for hygiene and health purposes.

Specific content

Careful usage is required to avoid potential negative effects on human health and the environment.

Common Uses

Antimicrobial agent

Properties

Strong antibacterial and antifungal

Applications

Disinfectants, preservatives, and sanitizing agents

Product Range

Soaps, shampoos, lotions, and wound care formulations

Precaution

Health risks if not handled properly

InChI:InChI=1/C8H8Br2O/c1-4-3-6(9)8(11)7(10)5(4)2/h3,11H,1-2H3

Upstream product

• 95-65-8 3,4-Dimethylphenol 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 

Downstream Products

• 71967-48-1 2,6-dibromo-4-bromomethyl-3-methyl-phenol 
• 1313182-88-5 [2-bromo-3,4-dimethyl-6-(trimethylsilyl)phenoxy]trimethylsilane 
• 1313182-89-6 [6-bromo-3,4-dimethyl-2-(trimethylsilyl)phenoxy]trimethylsilane 

Relevant articles and documents

Ortho-selective nucleophilic addition of primary amines to silylbenzynes: Synthesis of 2-silylanilines

Cause and effect: The first ortho-selective nucleophilic addition reaction of amines to 3-substituted benzynes has been achieved. Despite a large trimethylsilyl substituent, primary amines attack the C2 position of 3-silylbenzynes to produce 2-silylanilines (see scheme). This outcome is likely to result from the inductive electron-donating effect of the silyl group, which overrides its steric repulsion with the approaching amines. Copyright

Understanding solid/solid organic reactions

The concept of an organic reaction between two macroscopic solid particles is investigated. Thus, we study several reactions that have been recently reported to proceed "in the solid phase" and clearly show that, in most cases, grinding the two solid reactants together results in the formation of a liquid phase. This is true both for catalytic transformations (e.g., aldol condensations and oligomerization of benzylic compounds) and for noncatalytic reactions (Baeyer - Villiger oxidations, oxidative coupling of naphthols using iron chloride, condensation of amines and aldehydes to form azomethines, homo-etherification of benzylic alcohols using p-toluenesulfonic acid, and nuclear aromatic bromination with NBS). This liquefaction implies the existence of a eutectic mixture with Tfusion below ambient temperature (although both reagents have higher than ambient melting points). In cases where heating is required, it is again clear that a phase change (from solid to liquid) occurs, explaining the observed reaction kinetics. On the basis of 19 experimental examples, we discuss the possibility of solid-phase organic reactions and the implications of these findings to the reaction between two solid reagents. A general description of such reactive systems is proposed, based on a consideration of the potential for eutectic (or peritectic) formation between the constituents of the liquid phases that arise during the process of mechanical mixing of the solid reagents and products.

Halogenation Using Quaternary Ammonium Polyhalides. IV. Selective Bromination of Phenols by Use of Tetraalkylammonium Tribromides

Reaction of phenols with calculated amounts of benzyltrimethylammonium tribromide or tetrabutylammonium tribromide in dichloromethane-methanol for 0.5-1 h under mild conditions gave, selectively, the objective mono-, di-, or tribromophenols in good yields.

ipso Halogenation. II. Bromination of phenols, isomerisation and disproportionation of bromophenols, and dione-phenol rearrangement of bromodienones

Bromination of p-cresol, bromo-p-cresol, 3,4-dimethylphenol, and mesitol in trifluoromethanesulfonic acid gices as the main product the bromo derivative with bromine meta to hydroxyl, a result attributed to the intermediate formation of a bromodienone and its rearrangement.Phenols does not give m-bromophenol in trifluoromethanesulfonic acid. 4-Bromo-2,4,6-trimethylcyclohexa-2,5-dienone rearranges to 3-bromomesitol in trifluoromethanesulfonic acid and, similarly, 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone rearranges to 3-bromomesitol in trifluoromethanesulfonic acid and, similarly, 2,4,6-tribromo-4-methylcyclohexa-2,5-dienone rearranges to 2,3,6-tribromo-4-methylphenol.Under appropriate conditions debromination of bromodienones is competitive with rearrangement.Tetramethylammonium bromide in trifluoromethanesulfonic acid is an effective reagent for isomerization and disproportionation of bromophenols.Tetramethylammonium iodide in trifluoromethanesulfonic acid is an effective reagent for selective debromination of bromophenols at the ortho and para position.