874-98-6

Basic information

• Product Name: 3-METHOXYBENZYL BROMIDE
• Synonyms: 3-(BroMoMethyl)phenyl Methyl Ether;3-Methoxy-1-(broMoMethyl)benzene;3-Methoxylbenzyl BroMide;3-Methoxyphenyl)Methyl broMide;M-(BroMoMethyl)anisole;1-(BroMMethyl)-3-Methoxybenzol;3-(Bromomethyl)anisole, 1-(Bromomethyl)-3-methoxybenzene, 3-(Bromomethyl)phenyl methyl ether;3-Methoxybenzyl broMide, 98+%, 98+%
• CAS NO: 874-98-6
• Molecular Formula: C₈H₉BrO
• Molecular Weight: 201.06
• Product Categories: Methyl Halides;Phenyls & Phenyl-Het;Methyl Halides;Phenyls & Phenyl-Het;Aromatics;Catalyst;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 874-98-6.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 152 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.436 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0567mmHg at 25°C
• Refractive Index: n20/D 1.575(lit.)
• Storage Temp.: -20?C Freezer
• CAS DataBase Reference: 3-METHOXYBENZYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXYBENZYL BROMIDE(874-98-6)
• EPA Substance Registry System: 3-METHOXYBENZYL BROMIDE(874-98-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 874-98-6(Hazardous Substances Data)

Usage

Description

3-Methoxybenzyl bromide, also known as 1-bromomethyl-3-methoxybenzene, is a benzyl bromide derivative characterized by the presence of a methoxy group attached to a benzene ring and a bromine atom attached to the benzyl group. This organic compound is known for its reactivity and is commonly used in various chemical reactions and synthesis processes.

Uses

Used in Catalysts:
3-Methoxybenzyl bromide is used as a benzyl group rearrangement catalyst in chemical reactions. Its unique structure allows it to facilitate the rearrangement of benzyl groups, making it a valuable component in various organic synthesis processes.
Used in Pharmaceutical Industry:
3-Methoxybenzyl bromide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to participate in diastereoselective alkylation reactions with vicinal dianions of chiral succinic acid derivatives makes it a versatile building block for the development of new drugs.
Used in Organic Synthesis:
3-Methoxybenzyl bromide is used in the synthesis of a range of organic compounds, including:
1. 6-(3-methoxyphenyl)-hexane-2,4-dione: A compound that can be used as a precursor in the synthesis of various organic molecules.
2. N-(3-methoxybenzyl)-N-(1-methyl-1-phenylethyl)-amine: A compound with potential applications in the development of pharmaceuticals and other organic compounds.
3. 2-(3-methoxybenzyl)-3-[(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-(3S)-2-thionia-bicyclo[2.2.1]heptane tetrafluoroborate: A complex organic molecule with potential applications in various fields.
4. 1-(3-methoxybenzyl)-5-(1-methyl-1H-imidazol-5-yl)-1H-1,2,3-triazole: A compound that can be used as a building block in the synthesis of various organic molecules and pharmaceuticals.

InChI:InChI=1/C8H9BrO/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,6H2,1H3

Upstream product

• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 1058648-97-7 3-methoxy-1-[(ethoxymethoxy)methyl]benzene 
• 161358-52-7 3-methoxy-1-(methoxymethoxy)methyl benzene 
• 591-31-1 3-methoxy-benzaldehyde 
• 586-38-9 3-Methoxybenzoic acid 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 59276-28-7 m-anisaldehyde dimethyl acetal 
• 6971-51-3 3-methoxybenzyl alcohol 

Downstream Products

• 122767-15-1 2-benzoyl-1-(3-methoxy-benzyl)-pyridinium; picrate 
• 191860-78-3 (3-methoxy-benzyl)-(2-methoxy-phenyl)-ether 
• 15184-99-3 N,N-dimethyl-3-methoxybenzylamine 
• 27958-95-8 N,N-diethyl-3-(methoxyl)benzenemethanamine 
• 74-84-0 ethane 
• 10568-38-4 3-ethylanisole 
• 36707-27-4 1,2-bis(3-methoxyphenyl)ethane 
• 708257-60-7 bis-(3-methoxy-benzyl)-malonic acid diethyl ester 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 150254-05-0 2-[2-(3-Methoxy-phenyl)-ethyl]-3,5,6-trimethyl-pyran-4-one 
• 31559-00-9 2-[(3-methoxyphenyl)-methyl]cyclohexanone 
• 77784-80-6 1,2,3,4-tetrahydro-7-methoxy-2-(3-methoxybenzyl)-1-methylene-β-carboline 
• 30615-77-1 1-(3-Methoxybenzyl)-1-cyan-2-benzoyl-1,2-dihydroisochinolin 

Relevant articles and documents

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition

A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1