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215023

Sigma-Aldrich

3-Iodothiophene

≥97%

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About This Item

Empirical Formula (Hill Notation):
C4H3IS
CAS Number:
10486-61-0
Molecular Weight:
210.04
EC Number:
234-009-8
MDL number:
MFCD00037901
UNSPSC Code:
12352100
PubChem Substance ID:
24852862
NACRES:
NA.22

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

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[1]. It was also used in the preparation of 3-(perfluorooctyl)thiophene, required for the synthesis of poly(3-perfluorooctylthiophene) conjugated polymer[2].

Storage Class

10 - Combustible liquids

wgk_germany

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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Certificates of Analysis (COA)

Lot/Batch Number
MKBV2845V
MKBN6901V
MKBC2202
11321KE
10816AO

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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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