21852-32-4

Basic information

• Product Name: 3,4-DIMETHOXYBENZYL BROMIDE
• Synonyms: 3,4-DIMETHOXYBENZYL BROMIDE;4-(BroMoMethyl)-1,2-diMethoxybenzene;3,4-DiMethoxybenzyl BroMide Discontinued due to stability;Veratryl bromide;Benzene, 4-(broMoMethyl)-1,2-diMethoxy-;Toluene, α-bromo-3,4-dimethoxy-
• CAS NO: 21852-32-4
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.08644
• Product Categories: Aromatics;Miscellaneous Reagents
• Mol File: 21852-32-4.mol
• Article Data: 65

Chemical Properties

• Melting Point: 56-58℃
• Boiling Point: 273℃
• Flash Point: 116℃
• Appearance: /
• Density: 1.384
• Vapor Pressure: 0.00991mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: CDCl3
• CAS DataBase Reference: 3,4-DIMETHOXYBENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYBENZYL BROMIDE(21852-32-4)
• EPA Substance Registry System: 3,4-DIMETHOXYBENZYL BROMIDE(21852-32-4)

Safety Data

• Hazardous Substances Data: 21852-32-4(Hazardous Substances Data)

Usage

Description

3,4-DIMETHOXYBENZYL BROMIDE is an organic compound characterized by the presence of two methoxy groups at the 3rd and 4th positions of a benzene ring, with a bromine atom attached to the benzyl carbon. It is a valuable intermediate in the synthesis of various organic compounds and pharmaceuticals due to its unique chemical structure and reactivity.

Uses

Used in Chemical Synthesis:
3,4-DIMETHOXYBENZYL BROMIDE is used as a reagent for dimethoxybenzyl alkylations, a type of chemical reaction that involves the transfer of an alkyl group to another molecule. This process is essential in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-DIMETHOXYBENZYL BROMIDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique chemical structure allows for the development of novel therapeutic agents with potential applications in treating a wide range of diseases and medical conditions.
Used in Research and Development:
3,4-DIMETHOXYBENZYL BROMIDE is also utilized in research and development laboratories for the exploration of new chemical reactions and the synthesis of novel compounds. Its versatility as a reagent makes it a valuable tool for chemists working on the design and development of new molecules with potential applications in various industries.

InChI:InChI=1/C9H11BrO2/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-5H,6H2,1-2H3

Upstream product

• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 494-99-5 1,2-dimethoxy-4-methylbenzene 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 93-07-2 Veratric acid 

Downstream Products

• 198127-95-6 5-(3,4-dimethoxybenzyl)-1-dimethylsulfamoyl-4-iodoimidazole 
• 199444-24-1 2-(3,4-Dimethoxy-benzyloxy)-6-(3,5-dimethoxy-benzyloxy)-phenol 
• 6380-23-0 3,4-dimethoxystyrene 
• 6379-72-2 1,2-dimethoxy-4-(E)-propenylbenzene 
• 68719-75-5 (E)-4-(hex-1-en-1-yl)-1,2-dimethoxybenzene 
• 888701-47-1 5,6-dimethoxy-2,2-bis(3,4-dimethoxybenzyl)-2,3-dihydro-1H-indene-1,3-dione 
• 873336-79-9 5-[2-(3,4-dimethoxy-phenyl)-ethyl]-6-methoxy-2,2,7,8-tetramethyl-chroman 
• 873336-77-7 5-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-6-methoxy-2,2,7,8-tetramethyl-chroman 
• 873336-80-2 4-[2-(6-methoxy-2,2,7,8-tetramethyl-chroman-5-yl)-ethyl]-benzene-1,2-diol 
• 85524-69-2 2,3-dihydro-2-phenyl-5,6-dimethoxyinden-1-one 

Relevant articles and documents

Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction

The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.

New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents

A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.

Hydrothermal Liquefaction of α-O-4 Aryl Ether Linkages in Lignin

By using lignin model compounds with relevant key characteristic structural features, the reaction pathways of α-O-4 aryl ether linkages under hydrothermal conditions are elucidated. Experimental results and computational modeling suggest that the α-O-4 linkages in lignin undergo catalyzed hydrolysis and elimination to give phenolic and alkenylbenzene derivatives as major products in subcritical water. The decreased relative permittivity of water at these high temperatures and pressures facilitates the elimination reactions. The alkyl group on the α-carbon and the methoxy groups on the phenyl rings both have positive effects on the rate of conversion of α-O-4 linkages in native lignin.