1131-40-4

Basic information

• Product Name: 1-BROMO-2,4,6-TRIMETHOXYBENZENE
• Synonyms: RARECHEM AH CK 0052;1-BROMO-2,4,6-TRIMETHOXYBENZENE;2-BROMO-1,3,5-TRIMETHOXYBENZENE;2,4,6-TRIMETHOXYBROMOBENZENE;BROMO-2,4,6-TRIMETHOXYBENZENE;1-Bromo-2,4,6-trimethoxybenzene 98%;2,4,6-Trimethoxyphenyl bromide;2-Bromo-1,3,5-trimethoxybenzene 98%
• CAS NO: 1131-40-4
• Molecular Formula: C₉H₁₁BrO₃
• Molecular Weight: 247.09
• EINECS: 214-464-9
• Product Categories: Aromatic Ethers
• Mol File: 1131-40-4.mol
• Article Data: 50

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 303.5 °C at 760 mmHg
• Flash Point: 122 °C
• Appearance: /
• Density: 1.391 g/cm³
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-BROMO-2,4,6-TRIMETHOXYBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,4,6-TRIMETHOXYBENZENE(1131-40-4)
• EPA Substance Registry System: 1-BROMO-2,4,6-TRIMETHOXYBENZENE(1131-40-4)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• Hazardous Substances Data: 1131-40-4(Hazardous Substances Data)

Usage

General Description

1-Bromo-2,4,6-trimethoxybenzene is a chemical compound with the molecular formula C9H11BrO3. It is a brominated benzene derivative with three methoxy groups attached at the 2, 4, and 6 positions. 1-BROMO-2,4,6-TRIMETHOXYBENZENE is primarily used in organic synthesis as a building block for the production of various pharmaceuticals and agrochemicals. It is also of interest in the field of medicinal chemistry due to its potential as a pharmacological agent. 1-Bromo-2,4,6-trimethoxybenzene is a colorless to pale yellow liquid with a characteristic aromatic odor, and it should be handled with care due to its potential health hazards and environmental impact.

InChI:InChI=1/C9H11BrO3/c1-11-6-4-7(12-2)9(10)8(5-6)13-3/h4-5H,1-3H3

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 857802-23-4 5-bromo-2,4,6-trimethoxy-isophthalic acid 
• 77-78-1 dimethyl sulfate 
• 7726-95-6 bromine 
• 63458-84-4 5-bromo-2,4,6-trihydroxy-isophthalic acid diethyl ester 
• 857802-21-2 5-bromo-2,4,6-trimethoxy-isophthalic acid diethyl ester 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 106-42-3 para-xylene 
• 106-38-7 para-bromotoluene 
• 667-27-6 Ethyl bromodifluoroacetate 

Downstream Products

• 108170-07-6 1,3,5-trimethoxy-2-phenoxy-benzene 
• 98437-42-4 2-bromo-3,5-dimethoxycyclohexane-2,5-diene-1,4-dione 
• 119529-55-4 1,3,5-Trimethoxy-2-<(1R,2R,3S,4R,5R)-2,3,4,5,6-pentabenzyloxy-1-hydroxyhexyl>benzol 
• 119529-56-5 1,3,5-Trimethoxy-2-<(1S,2R,3S,4R,5R)-2,3,4,5,6-pentabenzyloxy-1-hydroxyhexyl>benzol 
• 86762-94-9 2,4,6-Trimethoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 
• 58235-51-1 2,4,6,3',4',5'-hexamethoxydiphenyl ether 
• 58235-53-3 2,4,6,2',4',6'-Hexamethoxydiphenylether 
• 330936-14-6 3,5,7,3',4'-penta-O-benzyl-4-hydroxy-4-(2,4,6-trimethoxyphenyl)epicatechin 
• 690666-83-2 1-(2-aminophenyl)-1-(2,4,6-trimethoxyphenyl)ethanol 
• 900501-59-9 (2,5-dibenzyloxyphenyl)(2,4,6-trimethoxyphenyl)methanone 
• 690666-84-3 1-amino-2-[1-(2,4,6-trimethoxyphenyl)ethenyl]benzene 
• 690666-66-1 1-isocyano-2-[1-(2,4,6-trimethoxyphenyl)ethenyl]benzene 
• 690666-85-4 N-{2-[1-(2,4,6-trimethoxyphenyl)ethenyl]phenyl}formamide 
• 330936-16-8 4α-(2,4,6-trimethoxyphenyl)epicatechin 

Relevant articles and documents

Characterization of a Cyanobacterial Haloperoxidase and Evaluation of its Biocatalytic Halogenation Potential

Vanadium-dependent haloperoxidases (VHPOs) are a class of halogenating enzymes found in fungi, lichen, algae, and bacteria. We report the cloning, purification, and characterization of a functional VHPO from the cyanobacterium Acaryochloris marina (AmVHPO), including its structure determination by X-ray crystallography. Compared to other VHPOs, the AmVHPO features a unique set of disulfide bonds that stabilize the dodecameric assembly of the protein. Easy access by high-yield recombinant expression, as well as resistance towards organic solvents and temperature, together with a distinct halogenation reactivity, make this enzyme a promising starting point for the development of biocatalytic transformations.

Vanadium-catalyzed oxidative bromination under atmospheric oxygen

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Discrete spherical hexadecavanadates incorporating a bromide with oxidative bromination activity

Two discrete hexadecavanadates, (n-Bu4N)4[V 16O38(X)] (X = Cl- (1) and X = Br- (2)), were synthesized by a reaction of [V10O26] 4- with a template anion resulting in the incorporation of chloride or bromide in the {V16} spherical cluster framework. The reaction of [V 10O26]4- with p-toluenesulfonic acid proceeded under an aerobic environment to give 2 in the presence of an excess amount of bromide anion, which acted as both a template anion and a reducing reagent for the formation of the mixed-valence framework. For the synthesis of cluster 1, additional reductive conditions were required due to the weak reducing ability of the chloride anion. The crystal structures of 1 and 2 were determined using single-crystal X-ray diffraction analysis. Both were found to consist of a discrete [VV9VIV7O 38(X)]4- framework by the linkage of VO5 pyramidal units. Cyclic voltammetric studies of 1 and 2 in acetonitrile showed a series of stepwise reversible redox processes, which were due to the redox of the spherical polyoxovanadate frameworks. The oxidative bromination reactions of aromatic substrates were also investigated using cluster 2 as a catalyst under aerobic conditions. The Royal Society of Chemistry.

Indole-Catalyzed Bromolactonization in Lipophilic Solvent: A Solid-Liquid Phase Transfer Approach

We have developed a novel indole-catalyzed bromolactonization of olefinic acids. The reaction could be conducted in lipophilic solvent through a solid-liquid phase transfer mechanism. This catalytic protocol has been applied to the synthesis of base-sensitive bromolactones. (Chemical Equation Presented).

Hydrogen-Bond-Donor Solvents Enable Catalyst-Free (Radio)-Halogenation and Deuteration of Organoborons

A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal-free, strong oxidant-free, more straightforward conditions).

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.