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750093

Sigma-Aldrich

3,4-Diaminothiophene dihydrochloride

97%

Synonym(s):

3,4-Thiophenediamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C4H6N2S · 2HCl
CAS Number:
Molecular Weight:
187.09
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Assay

97%

form

solid

mp

240-245 °C

SMILES string

Cl.Cl.Nc1cscc1N

InChI

1S/C4H6N2S.2ClH/c5-3-1-7-2-4(3)6;;/h1-2H,5-6H2;2*1H

InChI key

RAMOMCXNLLLICQ-UHFFFAOYSA-N

General description

This material is a synthetic intermediate for organic electronics materials such as Arylenediimide-thiophene Derivatives for Organic n-channel field-effect transistors. 1
They are also integral to the synthesis of thienopyrazine-based materials as low band gap materials for Organic Photovoltaic applications2 and as copolymer units for sensor applications.3

Application

3,4-Diaminothiophene dihydrochloride can be used in the synthesis of thieno[3,4-b]pyrazine for thermoelectric applications. It can also be used in the synthesis of acenaphtho[1,2-b]thieno[3,4-e]pyrazine based acceptor molecules for the fabrication of organic transistors.

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Rocío Ponce Ortiz et al.
Journal of the American Chemical Society, 132(24), 8440-8452 (2010-06-04)
The synthesis, structural, electrochemical, and thin film electrical and electronic structural properties of a series of arylene diimide-oligothiophene n-type semiconductors are reported. This family of compounds allows analysis of the effects on thin film transistor performance of the following: (i)
In Situ Oxidation Synthesis of p-Type Composite with Narrow-Bandgap Small Organic Molecule Coating on Single-Walled Carbon Nanotube: Flexible Film and Thermoelectric Performance
Gao C and Chen G
Small, 14(12), 1703453-1703453 (2018)
Li Wen et al.
The Journal of organic chemistry, 73(21), 8529-8536 (2008-10-09)
Synthetic methods have been developed for the preparation of new 2,3-dihalothieno[3,4-b]pyrazines, from which a variety of new 2,3-difunctionalized thieno[3,4-b]pyrazines have been produced as precursors to conjugated materials. Structural, electronic, and optical characterization of these new analogues illustrate the extent to
Zou; Y.; Wan; M.; Sang; G.; Ye; M.; Li; Y.
Advances in Functional Materials, 18, 2724-2732 (2008)
Transistor and solar cell performance of donor-acceptor low bandgap copolymers bearing an acenaphtho [1, 2-b] thieno [3, 4-e] pyrazine (ACTP) motif
Becerril H, et al.
Journal of Materials Chemistry, 19(5), 591-593 (2009)

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