Methyl 5-cyano-2-methoxybenzoate

Base Information

• Chemical Name: Methyl 5-cyano-2-methoxybenzoate
• CAS No.: 40757-12-8
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2926907090
• DSSTox Substance ID: DTXSID70594103
• Nikkaji Number: J2.761.175C
• Wikidata: Q82488835
• Mol file: 40757-12-8.mol

Synonyms:METHYL 5-CYANO-2-METHOXYBENZOATE;40757-12-8;5-cyano-2-methoxy-benzoic acid methyl ester;SCHEMBL385459;Methyl5-cyano-2-methoxybenzoate;DTXSID70594103;methyl 2-methoxy-5-cyanobenzoate;PIXOBZFOAGWQGO-UHFFFAOYSA-N;MFCD11044990;AKOS006308107;BS-28380;DB-320045;CS-0133300;A856646

Chemical Property of Methyl 5-cyano-2-methoxybenzoate

Chemical Property:

• PSA: 59.32000
• LogP: 1.35348
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-cyano-2-methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C#N)C(=O)OC

Technology Process of Methyl 5-cyano-2-methoxybenzoate

There total 8 articles about Methyl 5-cyano-2-methoxybenzoate 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: 93.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 3-bromo-4-methoxybenzonitrile (117572-79-9) → 3-methoxycarbonyl-4-methoxy-benzonitrile (40757-12-8)

Guidance literature:

With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; at 100 ℃; for 4h; under 3102.97 Torr;

Reference yield: 92.0%

methyl 5-((hydroxyimino)methyl)-2-methoxybenzoate (191605-12-6) → 3-methoxycarbonyl-4-methoxy-benzonitrile (40757-12-8)

Guidance literature:

With thionyl chloride; In dichloromethane; at 0 ℃; for 2h;

Reference yield: 72.0%

trimethylsilyl cyanide (7677-24-9) + 2-methoxybenzoic acid methyl ester (606-45-1) → 3-methoxycarbonyl-4-methoxy-benzonitrile (40757-12-8)

Guidance literature:

2-methoxybenzoic acid methyl ester; With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; oxygen; In acetonitrile; for 0.0833333h;

trimethylsilyl cyanide; In aq. phosphate buffer; acetonitrile; for 20h; pH=9; Irradiation;

DOI:10.1021/jacs.6b12708

upstream raw materials:

methyl 5-((hydroxyimino)methyl)-2-methoxybenzoate

methyl 5-bromo-2-methoxybenzoate

dicyanozinc

methanol

Downstream raw materials:

methyl 2-methoxy-5-(1H-tetrazol-5-yl)benzoate

methyl 5-carbamothioyl-2-methoxybenzoate

5-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]-2-hydroxybenzoic acid

6-methoxyisophthalamic acid

Refernces

• 1、 Lovering, Frank,Morgan, Paul,Allais, Christophe,Aulabaugh, Ann,Brodfuehrer, Joanne,Chang, Jeanne,Coe, Jotham,Ding, WeiDong,Dowty, Heather,Fleming, Margaret,Frisbie, Richard,Guzova, Julia,Hepworth, David,Jasti, Jayasankar,Kortum, Steve,Kurumbail, Ravi,Mohan, Shashi,Papaioannou, Nikolaos,Strohbach, Joseph W.,Vincent, Fabien,Lee, Katherine,Zapf, Christoph W.. "Rational approach to highly potent and selective apoptosis signal-regulating kinase 1 (ASK1) inhibitors". . p. 606 - 621. Retrieved 2018/01/19.
• 2、 Zhu, Yamin,Zhao, Mengdi,Lu, Wenkui,Li, Linyi,Shen, Zengming. "Acetonitrile as a cyanating reagent: Cu-catalyzed cyanation of arenes". supporting information. p. 2602 - 2605. Retrieved 2015/06/16.