THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

225-227

Boiling point:

386.7±22.0 °C(Predicted)

Density 

1.601±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

powder to crystal

pka

3.40±0.30(Predicted)

color 

White to Yellow to Green

InChI

InChI=1S/C7H4O2S2/c8-7(9)6-3-5-4(11-6)1-2-10-5/h1-3H,(H,8,9)

InChIKey

GVZXSZWCZGKLRS-UHFFFAOYSA-N

SMILES

C12C=CSC=1C=C(C(O)=O)S2

CAS DataBase Reference

1723-27-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-37/39-39

HazardClass 

IRRITANT

HS Code 

29349990

THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID Usage And Synthesis

Uses

Thieno[3,2-b]thiophene-2-carboxylic Acid has been used as a reactant for versatile α,ω-disubstituted tetratienoacene semiconductors for high performance organic thin-film transistors.

Definition

ChEBI: Thieno[3,2-b]thiophene-2-carboxylic acid is a thienothiophene.

Synthesis

Lithium hydroxide monohydrate (17.8 kg, 662.4 mol, 1.47 eq.) with deionized water (440.0 kg) was added to a 2000 L autoclave under a nitrogen atmosphere and stirred until completely dissolved. Subsequently, ethyl thieno[3,2-b]thiophene-2-carboxylate (95.5 kg, 449.8 mol, 1.0 eq.) was pumped into the reaction mixture at room temperature and tetrahydrofuran (379.5 kg) was added. The reaction mixture was heated to reflux (about 100°C) and maintained for 3 hours. Upon completion of the reaction, it was cooled to 35-40°C and the tetrahydrofuran was removed by rotary evaporation under reduced pressure under nitrogen atmosphere. Deionized water (200 kg) was added to the reaction vessel and the temperature was controlled to be below 20°C. The reaction mixture was filtered and the filter cake was washed three times with cold water (20 kg) and the residual liquid was removed by centrifugation to give the final thieno[3,2-b]thiophene-2-carboxylic acid (146 kg, 100% yield).

References

[1] Patent: CN103172646, 2016, B. Location in patent: Paragraph 0108-0110
[2] Macromolecules, 2013, vol. 46, # 6, p. 2078 - 2091
[3] Advanced Functional Materials, 2012, vol. 22, # 1, p. 48 - 60
[4] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 22, p. 3465 - 3470
[5] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2248 - 2255

THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID(1723-27-9)Related Product Information

• Thieno[3,2-b]thiophene-2-boronic Acid (contains varying amounts of Anhydride)
• Thieno[3,2-b]thiophene-2-carbonitrile
• thieno[3,2-b]thiophene-2-sulfonyl chloride
• Thieno[3,2-b]thiophene-2,5-dicarboxaldehyde
• Thiazole-5-carboxylic acid
• THIAZOLE-2-CARBOXYLIC ACID
• ETHYL THIAZOLE-4-CARBOXYLATE
• Thieno[3,2-b]thiophene
• thieno[3,2-b]thiophene-2,5-dicarboxylic acid
• Thieno[3,2-b]thiophene-3-sulfonyl chloride
• Thieno[3,2-c]pyridine-2-carboxylic acid methyl ester
• Thieno[3,2-b]thiophene-3-ol
• Thieno[3,2-b]thiophene-2-carboxaldehyde
• 1,3-Dihydrothiopheno[3,2-d]pyrimidine-2,4-dione
• Thieno[2,3-b]pyridine (8CI,9CI)
• THIENO[2,3-B]THIOPHENE-2-CARBOXYLIC ACID
• THIENO[3,2-B]THIOPHENE-2-CARBOXYLIC ACID
• METHYL THIENO[3,2-B!THIOPHENE-2-CARBOXYLATE, 97