Dimethyl 1-benzothiophene-5,6-dicarboxylate

Base Information

• Chemical Name: Dimethyl 1-benzothiophene-5,6-dicarboxylate
• CAS No.: 98449-83-3
• Molecular Formula: C₁₂H₁₀O₄S
• Molecular Weight: 250.275
• DSSTox Substance ID: DTXSID801334046
• Nikkaji Number: J305.815H
• Mol file: 98449-83-3.mol

Synonyms:dimethyl 1-benzothiophene-5,6-dicarboxylate;98449-83-3;benzo[b]thiophene-5,6-dicarboxylic acid dimethyl ester;SCHEMBL19664232;DTXSID801334046

Chemical Property of Dimethyl 1-benzothiophene-5,6-dicarboxylate

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 250.02997997
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C2C(=C1)C=CS2)C(=O)OC

Technology Process of Dimethyl 1-benzothiophene-5,6-dicarboxylate

There total 1 articles about Dimethyl 1-benzothiophene-5,6-dicarboxylate 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: 65.0%

2,3-diformylthiophene (932-41-2) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → dimethyl benzothiophene-5,6-dicarboxylate (98449-83-3)

Guidance literature:

With tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;

Reference yield:

dimethyl benzothiophene-5,6-dicarboxylate (98449-83-3) → 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzo[b]thiophene-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid di-tert-butyl ester (1026292-72-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOH / methanol

2: 94 percent / acetic anhydride / 1 h / 130 °C

3: 1.) Et₃N, 2.) bromotris(pyrrolidino)phosphoniumhexafluorophosphate, diisopropylethylamine / 1.) dichloromethane, 1 h, 2.) overnight

With sodium hydroxide; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In methanol;

DOI:10.1021/jm9508907

Reference yield:

dimethyl benzothiophene-5,6-dicarboxylate (98449-83-3) → 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzo[b]thiophene-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid

Guidance literature:

Multi-step reaction with 4 steps

1: NaOH / methanol

2: 94 percent / acetic anhydride / 1 h / 130 °C

3: 1.) Et₃N, 2.) bromotris(pyrrolidino)phosphoniumhexafluorophosphate, diisopropylethylamine / 1.) dichloromethane, 1 h, 2.) overnight

4: TFA

With sodium hydroxide; acetic anhydride; triethylamine; N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; trifluoroacetic acid; In methanol;

DOI:10.1021/jm9508907

upstream raw materials:

2,3-diformylthiophene

dimethyl cis-but-2-ene-1,4-dioate

Downstream raw materials:

5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzo[b]thiophene-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid di-tert-butyl ester