52806-46-9

Basic information

• Product Name: 2-Bromo-4,5-dimethoxytoluene
• Synonyms: 2-Bromo-4,5-dimethoxytoluene;1-bromo-4,5-dimethoxy-2-methylbenzene
• CAS NO: 52806-46-9
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Aromatics, Miscellaneous Reagents
• Mol File: 52806-46-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 259.9°C at 760 mmHg
• Flash Point: 106.4°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 0.0204mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 2-Bromo-4,5-dimethoxytoluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4,5-dimethoxytoluene(52806-46-9)
• EPA Substance Registry System: 2-Bromo-4,5-dimethoxytoluene(52806-46-9)

Safety Data

• Hazardous Substances Data: 52806-46-9(Hazardous Substances Data)

Usage

Uses

2-Bromo-4,5-dimethoxytoluene is a building block that has been used as a reactant for the synthesis of xylopinine and catechol derivatives.

InChI:InChI=1/C9H11BrO2/c1-6-4-8(11-2)9(12-3)5-7(6)10/h4-5H,1-3H3

Upstream product

• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 24186-66-1 2-methyl-4,5-dimethoxybenzaldehyde 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 93-51-6 2-Methoxy-4-methylphenol 
• 83387-13-7 5-bromo-2-methoxy-4-methylphenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 7721-62-2 4,5-dimethoxy-2-methylbenzaldehyde 
• 959144-37-7 (4,5-dimethoxy-2-methylphenyl)boronic acid 
• 58814-69-0 4,5-dimethoxy-2-methyl-benzonitrile 
• 6286-46-0 2-bromo-4,5-dimethoxybenzoic acid 
• 7509-11-7 1,2-dimethoxy-4-methyl-5-nitrobenzene 
• 172376-01-1 3,4-Dimethoxy-6-methylphenyl(3,4-methylenedioxyphenyl)methanol 
• 3023-14-1 4-(4-Chlor-3-methyl-phenoxy)-5-methyl-veratrol 
• 18863-72-4 4-bromo-5-methylbenzene-1,2-diol 
• 53207-00-4 1-bromo-2-(bromomethyl)-4,5-dimethoxybenzene 
• 109305-98-8 2-bromo-4,5-dimethoxybenzonitrile 
• 1309831-72-8 (S)-(-)-1,2-dimethoxy-4-methyl-5-(p-tolylsulfinyl)benzene 
• 4747-98-2 S-(-)-Norlaudanosine 
• 1309831-82-0 (1S)-1-[4,5-dimethoxy-2-[(R)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1309831-77-3 (1S)-1-[4,5-dimethoxy-2-[(S)-p-tolylsulfinyl]benzyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Two Stereoinduction Events in One C?H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes

Herein we disclose the synthesis of original chiral scaffolds—ortho-orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C?H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo-stereoselective C?H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho-terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N-Biax and diphosphine BiaxPhos.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.