215023
3-Iodothiophene
≥97%
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About This Item
Empirical Formula (Hill Notation):
C4H3IS
CAS Number:
Molecular Weight:
210.04
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
234-009-8
MDL number:
Assay:
≥97%
Product Name
3-Iodothiophene, ≥97%
InChI key
WGKRMQIQXMJVFZ-UHFFFAOYSA-N
InChI
1S/C4H3IS/c5-4-1-2-6-3-4/h1-3H
SMILES string
Ic1ccsc1
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.)
functional group
iodo
storage temp.
2-8°C
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.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
172.4 °F - closed cup
flash_point_c
78 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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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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