Methyl 2-(bromomethyl)-5-cyanobenzoate

Base Information

• Chemical Name: Methyl 2-(bromomethyl)-5-cyanobenzoate
• CAS No.: 421551-82-8
• Molecular Formula: C10H8BrNO2
• Molecular Weight: 254.083
• Hs Code.: 2926909090
• European Community (EC) Number: 882-088-8
• Mol file: 421551-82-8.mol

Synonyms:METHYL 2-(BROMOMETHYL)-5-CYANOBENZOATE;421551-82-8;2-bromomethyl-5-cyano-benzoic acid methyl ester;MFCD18251143;SCHEMBL2084464;TWNPQXWVXHPIJV-UHFFFAOYSA-N;WRA55182;SC5124;AKOS022187408;AB74315;DS-8762;SY324831;DB-109154;METHYL2-(BROMOMETHYL)-5-CYANOBENZOATE;Benzoic acid, 2-(bromomethyl)-5-cyano-, methyl ester

Chemical Property of Methyl 2-(bromomethyl)-5-cyanobenzoate

Chemical Property:

• PSA: 50.09000
• LogP: 2.23978
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 252.97384
• Heavy Atom Count: 14
• Complexity: 258

Purity/Quality:

95% ^*data from raw suppliers

Methyl 2-(bromomethyl)-5-cyanobenzoate 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)C#N)CBr

Technology Process of Methyl 2-(bromomethyl)-5-cyanobenzoate

There total 9 articles about Methyl 2-(bromomethyl)-5-cyanobenzoate 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: 90.0%

5-cyano-2-methylbenzoic acid methyl ester (103261-68-3) → methyl 2-(bromomethyl)-5-cyanobenzoate (421551-82-8)

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80 ℃; for 12h;

Reference yield:

3-iodo-4-methylbenzonitrile (42872-79-7) → methyl 2-(bromomethyl)-5-cyanobenzoate (421551-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / Pd(dppf)Cl₂; Et₃N / 20 h / 120 °C / 23271.7 Torr

2: NBS; benzoyl peroxide / CCl₄ / 48 h / Heating

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; triethylamine; dibenzoyl peroxide; In tetrachloromethane;

DOI:10.1021/jm030434f

Reference yield:

5-bromo-2-methylaniline (39478-78-9) → methyl 2-(bromomethyl)-5-cyanobenzoate (421551-82-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 84 percent / Pd(PPh₃)4 / dimethylformamide / 2 h / 80 °C

2.1: aq. HCl; aq. NaNO₂ / acetone / 2 h / 0 °C

2.2: 70 percent / aq. KI / acetone / 6 h

3.1: 62 percent / Pd(dppf)Cl₂; Et₃N / 20 h / 120 °C / 23271.7 Torr

4.1: NBS; benzoyl peroxide / CCl₄ / 48 h / Heating

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; sodium nitrite; dibenzoyl peroxide; In tetrachloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm030434f

upstream raw materials:

5-cyano-2-methylbenzoic acid methyl ester

5-nitro-o-toluic acid

methyl 2-methyl-5-nitrobenzoate

methyl 5-amino-2-methylbenzoate

Downstream raw materials:

3-oxoisoindoline-5-carbonitrile