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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:
90069-81-1
Molecular Weight:
187.09
MDL number:
MFCD00671511
UNSPSC Code:
12352103
PubChem Substance ID:
329766046
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.[1] 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.[2]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK7785
MKCH3647
MKBX8341V
MKBQ8278V
MKBN4463V

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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
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)
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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