3-Methoxybenzyl bromide

Base Information

• Chemical Name: 3-Methoxybenzyl bromide
• CAS No.: 874-98-6
• Molecular Formula: C8H9BrO
• Molecular Weight: 201.063
• Hs Code.: 29049090
• European Community (EC) Number: 629-399-5
• DSSTox Substance ID: DTXSID50398969
• Nikkaji Number: J377.998J
• Wikidata: Q72489260
• Mol file: 874-98-6.mol

Synonyms:3-Methoxybenzyl bromide;874-98-6;1-(bromomethyl)-3-methoxybenzene;3-Methoxybenzylbromide;Benzene, 1-(bromomethyl)-3-methoxy-;3-methoxybenzylbromid;1-Bromomethyl-3-methoxybenzene;m-Methoxybenzyl bromide;1-bromomethyl-3-methoxy-benzene;3-methoxy benzylbromide;3-methoxy-benzylbromide;3-methoxylbenzyl bromide;3-methoxy benzyl bromide;3-methoxy-benzyl bromide;3-(methoxy)benzyl bromide;SCHEMBL17743;1bromomethyl-3-methoxy-benzene;3-Bromomethyl-3-methoxybenzene;3-Methoxybenzyl bromide, 98%;DTXSID50398969;ZKSOJQDNSNJIQW-UHFFFAOYSA-N;3-(bromomethyl)phenyl methyl ether;AC-566;CK2012;MFCD00216590;1-(bromomethyl)-3-(methyloxy)benzene;AKOS009156466;CS-W015575;AS-45846;AM20041283;FT-0655975;m-Methoxybenzylbromide;3-(Bromomethyl)anisole;A24610;EN300-108874;Q-200385

Chemical Property of 3-Methoxybenzyl bromide

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 0.0567mmHg at 25°C
• Refractive Index: n20/D 1.575(lit.)
• Boiling Point: 241.111 °C at 760 mmHg
• Flash Point: 95.446 °C
• PSA: 9.23000
• Density: 1.407 g/cm³
• LogP: 2.59010
• Storage Temp.: -20?C Freezer
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 199.98368
• Heavy Atom Count: 10
• Complexity: 95.3

Purity/Quality:

99.9% ^*data from raw suppliers

3-Methoxybenzyl bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC(=C1)CBr
• Uses: 3-Methoxybenzyl bromide is a benzyl bromide derivative used as a benzyl group rearrangement catalyst. 3-Methoxybenzyl bromide (1-bromomethyl-3-methoxybenzene) may be used in the diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives. It may be used in the synthesis of the following:6-(3-methoxyphenyl)-hexane-2,4-dioneN-(3-methoxybenzyl)-N-(1-methyl-1-phenylethyl)-amine2-(3-methoxybenzyl)-3-[(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-(3S)-2-thionia-bicyclo [2.2.1]- heptane tetrafluoroborate1-(3-methoxybenzyl)-5-(1-methyl-1H-imidazol-5-yl)-1H-1,2,3-triazole

Technology Process of 3-Methoxybenzyl bromide

There total 11 articles about 3-Methoxybenzyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-methoxybenzyl alcohol (6971-51-3) → 1-bromomethyl-3-methoxybenzene (874-98-6)

Guidance literature:

With phosphorus tribromide; In benzene; at 20 ℃;

DOI:10.1016/j.jsbmb.2013.02.009

Reference yield: 99.0%

m-anisaldehyde dimethyl acetal (59276-28-7) → 1-bromomethyl-3-methoxybenzene (874-98-6)

Guidance literature:

With triethylsilane; Acetyl bromide; tin(II) bromide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1246/bcsj.64.1410

Reference yield: 83.0%

3-methoxy-1-[(ethoxymethoxy)methyl]benzene (1058648-97-7) → 1-bromomethyl-3-methoxybenzene (874-98-6)

Guidance literature:

With tetrabutylammomium bromide; 1-(n-butyl)-3-methylimidazolium tetrachloroindate; at 135 - 140 ℃; for 0.0666667h; chemoselective reaction; Microwave irradiation; Neat (no solvent);

DOI:10.1016/j.tetlet.2010.04.056

upstream raw materials:

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

1-methoxy-3-methyl-benzene

3-methoxybenzyl alcohol

m-anisaldehyde dimethyl acetal

Downstream raw materials:

2-benzoyl-1-(3-methoxy-benzyl)-pyridinium; picrate

N,N-dimethyl-3-methoxybenzylamine

ethane

3-ethylanisole

Refernces

• 1、 Butts, Craig P.,Collingridge, Graham L.,Jane, David E.,Mallah, Shahida,Molnár, Elek,Re?nik, Lisa-Maria,Thatcher, Robert J.,Willis, Christine L.. "Synthesis and pharmacological characterisation of arctigenin analogues as antagonists of AMPA and kainate receptors". supporting information. p. 9154 - 9162. Retrieved 2021/11/16.
• 2、 Houle, Camille,Savoie, Paul R.,Davies, Clotilde,Jardel, Damien,Champagne, Pier Alexandre,Bibal, Brigitte,Paquin, Jean-Fran?ois. "Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides". supporting information. p. 10620 - 10625. Retrieved 2020/07/24.