607-99-8

Basic information

• Product Name: 2,4,6-TRIBROMOANISOLE
• Synonyms: 1,3,5-tribromo-2-methoxy-benzen;1,3,5-Tribromo-2-methoxybenzene;Anisole, 2,4,6-tribromo-;Methyl 2,4,6-tribromophenyl ether;AKOS 237-128;2,4,6-TRIBROMOMETHOXYBENZENE;2,4,6-TRIBROMO-1-METHOXYBENZENE;2,4,6-TRIBROMOANISOLE
• CAS NO: 607-99-8
• Molecular Formula: C₇H₅Br₃O
• Molecular Weight: 344.83
• Product Categories: Aromatics;Intermediates;Miscellaneous Reagents
• Mol File: 607-99-8.mol

Chemical Properties

• Melting Point: 84-88 °C(lit.)
• Boiling Point: 297-299 °C(lit.)
• Flash Point: 121.5 °C
• Appearance: White to pale brown/Solid
• Density: 2.4910
• Vapor Pressure: 0.00231mmHg at 25°C
• Refractive Index: 1.5580 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• BRN: 2210361
• CAS DataBase Reference: 2,4,6-TRIBROMOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIBROMOANISOLE(607-99-8)
• EPA Substance Registry System: 2,4,6-TRIBROMOANISOLE(607-99-8)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 607-99-8(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2,4,6-Tribromoanisole is used as a suitable reagent for the determination of its presence in packaging materials and food by an analytical method based on multiple ion detection gas chromatography-mass spectrometry (GC-MS). This application is crucial for ensuring the safety and quality of these products.
Used in Wine Industry:
In the wine industry, 2,4,6-tribromoanisole is identified as one of the main agents responsible for the musty odor in wine samples. Its detection and removal are essential for maintaining the quality and reputation of the wine produced. Various methods, such as vortex-assisted liquid-liquid microextraction (VALLME) and gas chromatography-high-resolution mass spectrometry (GC-HRMS), have been developed for its determination and quantification at low ngL-1 levels in wine.

InChI:InChI=1/C7H5Br3O/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 118-79-6 2,4,6-tribromophenol 
• 67-56-1 methanol 
• 21702-84-1 2,4-dibromoanisole 
• 133871-69-9 2,4,6-tribromo-5-methoxybenzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 2666-53-7 sodium 2,4,6-tribromophenolate 
• 77-78-1 dimethyl sulfate 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 1189-09-9 methyl geranate 
• 634-89-9 1,2,3,5-tetrabromobenzene 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 7726-95-6 bromine 

Downstream Products

• 13130-23-9 3,5-dibromo-2-methoxybenzoic acid 
• 99067-30-8 5-bromo-2-methoxyisophthalic acid 
• 873981-08-9 2,4,6-tribromo-3-nitro-anisole 
• 201349-27-1 2,4,6-tribromo-3,5-dinitro-anisole 
• 29267-67-2 2-methoxyresorcinol 
• 58922-29-5 2,4-dihydroxy-3-methoxybenzaldehyde 
• 96920-28-4 4,6-dibromo-2-(2,4-dibromophenoxy)anisole 
• 151799-72-3 2-methoxy-1,3,5-benzenetriyltris(N-tert-butyl-N-hydroxyamine) 
• 151799-70-1 5-bromo-2-methoxy-1,3-phenylenebis[N-tert-butyl-N-(tert-butyldimethylsilyloxy)amine] 
• 151799-71-2 5-(N-tert-butyl-N-hydroxyamino)-2-methoxy-1,3-phenylenebis(N-tert-butyl-N-(tert-butyldimethylsilyloxy)amine) 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 98273-59-7 4-bromo-2-iodo-anisole 
• 114303-65-0 2-allyl-4-bromo-1-methoxybenzene 
• 137464-94-9 4-bromo-2-(1-hydroxy-n-butyl)anisole 

Relevant articles and documents

Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes

A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.

Rapid and total bromination of aromatic compounds using TsNBr2 without any catalyst

N,N-Dibromo-p-toluenesulfonamide (TsNBr2) has been found to be a new reagent for bromination of aromatic compounds. The reaction is extremely fast and goes into completion instantaneously at ambient temperature to produce exclusively the corresponding polybrominated product. This procedure is applicable to various phenols, anisole, and anilines to give corresponding polybrominated compound as a single product in excellent yield.

SULFONYL ESTERS 1: THE REDUCTION OF TRIBROMOPHENYL SULFONATES WITH MERCAPTIDE ANIONS

2,4,6-tribromophenyl sulfonates have been shown to undergo unusually efficient reduction by mercaptide anions in hexamethylphosphoramide.The reduction products include the sulfinate anion derived from the sulfonate ester and the disulfide derived from the mercaptide anions.

POLYBROMINATED AROMATIC COMPOUNDS. IV. METHOXYDEBROMINATION REACTIONS OF POLYBROMOBENZENES IN PYRIDINE

The rates were measured and the orientation was studied for the methoxydebromination of all polybromobenzenes C6HnBr6-n (n = 0-3) in pyridine at 115 deg C.From comparison of the partial rates of substitution of the bromine atom at various positions of the benzene ring it was found that the activating effect of the bromine atom in relation to the point of nucleophilic attack changes in the order o-Br > m-Br > p-Br, and the directing selectivity of the bromine is low (compared with fluorine in the methoxydefluorination of polyfluorobenzenes) and increases with decrease in the number of bromine atoms in the aromatic ring of the substrate.

Selective Bromination of Polyenes by 2,4,4,6-tetrabromocyclohexa-2,5-dienone

2,4,4,6-Tetrabromocyclohexa-2,5-dienone (TBCO) liberates bromonium ion when treated with polyenes to form brominated products.The results of the reaction of TBCO with simple olefins are presented.The analogous bromo-ketones, 4-bromo-2,4,6-trichloro- and 2,4,6-tribromo-4-methyl-cyclohexa-2,5-dienone, (4) and (5) respectively, afford the same products (3a), (6), and (7) when treated with geranyl cyanide (1; R = CN).The evidence suggests that formation of the dibromide (3a) may be due to sequential reactions.TBCO in the presence of cetyltrimethylammonium bromide serves as an excellent reagent for selective bromination of polyenes under very mild conditions.