Diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate

Base Information

• Chemical Name: Diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate
• CAS No.: 4004-20-0
• Molecular Formula: C12H14 N2 O4 S2
• Molecular Weight: 314.386
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60373040
• Nikkaji Number: J1.648.820H
• Wikidata: Q82161146
• Mol file: 4004-20-0.mol

Synonyms:4004-20-0;diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate;SCHEMBL14586047;DTXSID60373040;AKOS004909369;3,4-DIAMINO-THIENO[2,3-B]THIOPHENE-2,5-DICARBOXYLIC ACID DIETHYL ESTER;diethyl3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate;3,4-Diaminothieno[2,3-b]thiophene-2,5-dicarboxylic acid diethyl ester

Chemical Property of Diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate

Chemical Property:

• PSA: 161.12000
• LogP: 3.64300
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 314.03949928
• Heavy Atom Count: 20
• Complexity: 362

Purity/Quality:

99%min ^*data from raw suppliers

3,4-Diamino-thieno[2,3-b]thiophene-2,5-dicarboxylic aciddiethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=C(S1)SC(=C2N)C(=O)OCC)N

Technology Process of Diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarboxylate

There total 4 articles about Diethyl 3,4-diaminothieno[2,3-b]thiophene-2,5-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: 95.0%

ethyl 3-amino-4-cyano-5-((ethoxycarbonyl)methylthio)thiophene-2-carboxylate (91568-02-4) → Diethyl 3,4-diaminothieno<2,3-b>thiophene-2,5-dicarboxylate (4004-20-0)

Guidance literature:

With sodium ethanolate; In ethanol; dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2008.07.036

Reference yield: 88.0%

carbon disulfide (75-15-0,12122-00-8) + chloroacetic acid ethyl ester (105-39-5) + malononitrile (109-77-3) → Diethyl 3,4-diaminothieno<2,3-b>thiophene-2,5-dicarboxylate (4004-20-0)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In benzene;

Reference yield: 83.0%

carbon disulfide (75-15-0,12122-00-8) + ethyl bromoacetate (105-36-2) + malononitrile (109-77-3) → Diethyl 3,4-diaminothieno<2,3-b>thiophene-2,5-dicarboxylate (4004-20-0)

Guidance literature:

carbon disulfide; malononitrile; With potassium carbonate; In N,N-dimethyl-formamide; for 0.5h;

ethyl bromoacetate; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1002/jhet.5570380521

upstream raw materials:

ethyl 3-amino-4-cyano-5-((ethoxycarbonyl)methylthio)thiophene-2-carboxylate

carbon disulfide

chloroacetic acid ethyl ester

malononitrile

Downstream raw materials:

bis[4-oxo-3-phenyl-1(H)-2-thioxothieno(3,2-d)pyrimidine]

3,4-dibenzoylaminothieno(2,3-b)thiophene-2,5-dicarboxamide

diethyl 3-amino-4-[(triphenylphosphoranylidene)amino]thieno[2,3-b]thiophene-2,5-dicarboxylate

Refernces

• 1、 Liu, Ming-Guo,Hu, Yang-Gen,Ding, Ming-Wu. "New iminophosphorane-mediated synthesis of thieno[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-ones and 5H-2,3-dithia-5,7-diaza-cyclopenta[c,d]indenes". . p. 9052 - 9059. Retrieved 2008/12/22.
• 2、 El-Shafei, A. K.,Abdel-Ghany, H. A.,Sultan, A. A.,El-Saghier, A. M. M.. "SYNTHESIS OF THIENO(2,3-b)THIOPHENES AND RELATED STRUCTURES". . p. 15 - 26. Retrieved 2007/10/02.