Methyl 4-(bromomethyl)-3-methylbenzoate

Base Information

• Chemical Name: Methyl 4-(bromomethyl)-3-methylbenzoate
• CAS No.: 104447-92-9
• Molecular Formula: C₁₀H₁₁BrO₂
• Molecular Weight: 243.1
• DSSTox Substance ID: DTXSID401281358
• Nikkaji Number: J2.662.920I
• Mol file: 104447-92-9.mol

Synonyms:104447-92-9;methyl 4-(bromomethyl)-3-methylbenzoate;SCHEMBL9479617;DTXSID401281358;DB-417252

Chemical Property of Methyl 4-(bromomethyl)-3-methylbenzoate

Chemical Property:

• Boiling Point: 312.9±30.0 °C(Predicted)
• Density: 1.404±0.06 g/cm3(Predicted)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 241.99424
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)C(=O)OC)CBr

Technology Process of Methyl 4-(bromomethyl)-3-methylbenzoate

There total 9 articles about Methyl 4-(bromomethyl)-3-methylbenzoate 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: 95.0%

4-hydroxymethyl-3-methylbenzoic acid methyl ester (24078-25-9) → 4-bromomethyl-3-methylbenzoic acid methyl ester (104447-92-9)

Guidance literature:

With phosphorus tribromide; In various solvent(s); at -6 ℃; for 0.5h;

DOI:10.1016/j.bmc.2006.08.001

Reference yield: 72.0%

methyl 3,4-dimethylbenzoate (38404-42-1) → 4-bromomethyl-3-methylbenzoic acid methyl ester (104447-92-9)

Guidance literature:

With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; potassium bromide; In water; at 120 ℃; under 750.075 Torr; Microwave irradiation;

DOI:10.1055/s-0034-1379005

Reference yield:

4-bromo-2-methylbenzoic acid (68837-59-2) → 4-bromomethyl-3-methylbenzoic acid methyl ester (104447-92-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 47 percent / lithium aluminum hydride / tetrahydrofuran / 0.17 h / 20 °C

2: 61 percent / triethylamine; dppf / Pd(OAc)2 / dimethylsulfoxide / 2 h / 70 °C

3: 95 percent / PBr₃ / various solvent(s) / 0.5 h / -6 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; lithium aluminium tetrahydride; phosphorus tribromide; triethylamine; palladium diacetate; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/j.bmc.2006.08.001

upstream raw materials:

4-hydroxymethyl-3-methylbenzoic acid methyl ester

4-bromo-2-methylbenzoic acid

4-bromo-2-methylbenzyl alcohol

methyl 3,4-dimethylbenzoate

Downstream raw materials:

4-(2-nitro-4, 5-dimethylphenoxymethyl)-3-methylbenzoic acid methyl ester

methyl 3-methyl-4-{[(6-nitro-2,3-dihydro-1H-inden-5-yl)oxy]methyl}benzoate

methyl 4-{[2-{isobutyl[(5-methyl-2-furyl)sulfonyl]amino}-5-(trifluoromethyl)phenoxy]methyl}-3-methylbenzoate

4-(2-amino-4, 5-dimethylphenoxymethyl)-3-methylbenzoic acid methyl ester