All Photos(1)

215023

Sigma-Aldrich

3-Iodothiophene

≥97%

Empirical Formula (Hill Notation):
C4H3IS
CAS Number:
Molecular Weight:
210.04
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥97%

contains

copper as stabilizer

refractive index

n20/D 1.657 (lit.)

bp

75 °C/14 mmHg (lit.)

density

2.066 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Ic1ccsc1

InChI

1S/C4H3IS/c5-4-1-2-6-3-4/h1-3H

InChI key

WGKRMQIQXMJVFZ-UHFFFAOYSA-N

Application

3-Iodothiophene was used in the synthesis of 3-thienylzinc iodide via reaction with zinc, followed by coupling with aryl halides. It was also used in the preparation of 3-(perfluorooctyl)thiophene, required for the synthesis of poly(3-perfluorooctylthiophene) conjugated polymer.

Packaging

1 g in glass bottle

Certificate of Analysis

Certificate of Origin

Tuning the Electronic Structure and Solubility of Conjugated Polymers with Perfluoroalkyl Substituents: Poly (3-perfluorooctylthiophene), the First Supercritical CO2-soluble Conjugated Polymer.
Li LING, et al.
Advanced Materials, 16(2), 180-183 (2004)
Preparation of 3-Thienylzinc and-magnesium Halide via Oxidative Addition of Active Zinc and Magnesium to 3-Iodothiophene.
Wu X and Rieke RD.
The Journal of Organic Chemistry, 60(21), 6658-6659 (1995)
Alexander Koch et al.
Dalton transactions (Cambridge, England : 2003), 47(36), 12534-12539 (2018-05-05)
The reduction of 2-bromo- and 3-bromothiophene with calcium powder gives impure thienylcalcium complexes due to interference of various subsequent metalation and calcium-halogen exchange reactions as well as ether degradation. Therefore, calcium-iodine exchange succeeds via the reaction of trimethylsilylmethylcalcium halide with...

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