2,5-Thiophenedicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 2,5-Thiophenedicarboxylic acid dimethyl ester
• CAS No.: 4282-34-2
• Molecular Formula: C8H8O4S
• Molecular Weight: 200.215
• Hs Code.: 2934999090
• European Community (EC) Number: 886-158-9
• DSSTox Substance ID: DTXSID601227144
• Nikkaji Number: J802.994F
• Mol file: 4282-34-2.mol

Synonyms:4282-34-2;2,5-Thiophenedicarboxylic acid dimethyl ester;dimethyl thiophene-2,5-dicarboxylate;2,5-dimethyl thiophene-2,5-dicarboxylate;Dimethyl 2,5-thiophenedicarboxylate;thiophene-2,5-dicarboxylic acid dimethyl ester;SCHEMBL70027;DTXSID601227144;dimethylthiophene-2,5-dicarboxylate;MFCD00142121;AKOS002350036;AS-9598;CS-0206544;FT-0652279;thiophene-2,5-dicarboxylic acid dimethylester;EN300-250213;AE-641/01995022;SR-01000510005;2,5-Thiophenedicarboxylic acid, 2,5-dimethyl ester;SR-01000510005-1;Z269906846

Chemical Property of 2,5-Thiophenedicarboxylic acid dimethyl ester

Chemical Property:

• Melting Point: 148.5-149.5 °C
• Boiling Point: 291.6 °C at 760 mmHg
• Flash Point: 130.2 °C
• PSA: 80.84000
• Density: 1.294 g/cm³
• LogP: 1.32130
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 200.01432991
• Heavy Atom Count: 13
• Complexity: 194

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl thiophene-2,5-dicarboxylate ^*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)C(=O)OC

Technology Process of 2,5-Thiophenedicarboxylic acid dimethyl ester

There total 5 articles about 2,5-Thiophenedicarboxylic acid dimethyl ester 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: 55.0%

2,5-dibromothiophen (3141-27-3) + carbon monoxide (201230-82-2) → Thiophene-2,5-dicarboxylic acid (4282-31-9) + Dimethyl thiophene-2,5-dicarboxylate (4282-34-2)

Guidance literature:

With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 54h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

Reference yield: 44.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) + methanol (67-56-1) + tetrachloromethane (56-23-5) → thiophene-2-carboxylic acid methyl ester (5380-42-7) + Dimethyl thiophene-2,5-dicarboxylate (4282-34-2)

Guidance literature:

With iron(III)-acetylacetonate; at 140 ℃; for 6h; Inert atmosphere; Autoclave;

DOI:10.1134/S0965544108060121

Reference yield: 17.0%

methanol (67-56-1) + 2,5-dibromothiophen (3141-27-3) + carbon monoxide (201230-82-2) → Thiophene-2,5-dicarboxylic acid (4282-31-9) + Dimethyl thiophene-2,5-dicarboxylate (4282-34-2)

Guidance literature:

With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate; In tetrahydrofuran; at 40 ℃; for 54h; under 760 Torr; Irradiation;

DOI:10.1021/jo00131a005

upstream raw materials:

acrylic acid methyl ester

methanol

2,5-dibromothiophen

carbon monoxide

Downstream raw materials:

2-thiophenylcarboxylic acid

thiophene-2-carboxylic acid methyl ester

Thiophene-2,5-dicarboxylic acid

4-nitro-2-thiophenecarboxylic acid

Refernces

• 1、 Marchal, Joel,Bodiguel, Jacques,Fort, Yves,Caubere, Paul. "A New Indirect Application of Aggregative Activation: Synthesis of Esters by Cobalt-Catalyzed Carbonylation of Aryl, Heterocyclic, and Vinyl Halides under Atmospheric Pressure". . p. 8336 - 8340. Retrieved 2007/10/02.