Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate
• CAS No.: 175202-48-9
• Molecular Formula: C₈H₇NO₂S₂
• Molecular Weight: 213.281
• Hs Code.: 2930909899
• European Community (EC) Number: 678-687-7
• DSSTox Substance ID: DTXSID50594904
• Nikkaji Number: J1.543.943B
• Wikidata: Q82489828
• Mol file: 175202-48-9.mol

Synonyms:175202-48-9;Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate;4-CYANO-5-METHYLSULFANYLTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;methyl 4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate;methyl 4-cyano-5-methylsulfanylthiophene-2-carboxylate;2-Thiophenecarboxylic acid, 4-cyano-5-(methylthio)-, methyl ester;MFCD00173757;2-Thiophenecarboxylicacid, 4-cyano-5-(methylthio)-, methyl ester;SCHEMBL6928589;DTXSID50594904;BBL101107;STL554903;AKOS005257002;TS-00438;DB-007682;CS-0316405;AS-938/43416188;methyl 4-cyano-5-(methylsulfanyl)-2-thiophenecarboxylate

Chemical Property of Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 2.32E-05mmHg at 25°C
• Melting Point: 117-119℃
• Boiling Point: 359.8°C at 760 mmHg
• Flash Point: 171.4°C
• PSA: 103.63000
• Density: 1.36g/cm³
• LogP: 2.12828
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 212.99182081
• Heavy Atom Count: 13
• Complexity: 248

Purity/Quality:

99% ^*data from raw suppliers

4-Cyano-5-methylsulfanylthiophene-2-carboxylic acid methyl ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(S1)SC)C#N

Technology Process of Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate

There total 2 articles about Methyl 4-Cyano-5-(methylthio)thiophene-2-carboxylate 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:

methyl 3-amino-4-cyano-5-(methylsulfanyl)-2-thiophenecarboxylate (129332-45-2) → methyl 4‐cyano‐5‐(methylthio)thiophene‐2‐carboxylate (175202-48-9)

Guidance literature:

With isopentyl nitrite; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/S0960-894X(01)00102-0

Reference yield:

[Bis(methylthio)methylene]malononitrile (5147-80-8) → methyl 4‐cyano‐5‐(methylthio)thiophene‐2‐carboxylate (175202-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / methanol

2: isoamyl nitrite / dimethylformamide / 70 °C

With triethylamine; isopentyl nitrite; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00102-0

Reference yield:

methyl 4‐cyano‐5‐(methylthio)thiophene‐2‐carboxylate (175202-48-9) → 4-cyano-5-[(3,5-dichloropyridin-4-yl)thio]-N-{4-[3-(dimethylamino)propoxy]phenyl} thiophene-2-carboxamide (1247825-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.83 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 0.17 h / 150 °C / Microwave irradiation

3.1: trimethylaluminum / dichloromethane; toluene / 0.75 h / -10 - 20 °C / Inert atmosphere

3.2: 20 °C / Reflux

3.3: 0.5 h

With trimethylaluminum; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ml200276j

upstream raw materials:

methyl 3-amino-4-cyano-5-(methylsulfanyl)-2-thiophenecarboxylate

[Bis(methylthio)methylene]malononitrile

Downstream raw materials:

methyl 4-cyano-5-[(4-methoxyphenyl)methylthio]thiophene-2-carboxylate

methyl 5-methoxy-4-(4-phenyl(1,3-thiazol-2-yl))thiophene-2-carboxylate

methyl 4-(aminothioxomethyl)-5-[(4-methoxyphenyl)methylthio]thiophene-2-carboxylate

5-(4-methoxy-benzylsulfanyl)-4-(4-phenyl-thiazol-2-yl)-thiophene-2-carboxylic acid methyl ester