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196150

2-Iodothiophene

Name: 2-Iodothiophene
Brand: ALDRICH

98%

Synonym(s):

α-Iodothiophene, 2-Thienyl iodide

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About This Item

Empirical Formula (Hill Notation):

C₄H₃IS

CAS Number:

3437-95-4

Molecular Weight:

210.04

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24851738

EC Number:

222-342-1

Beilstein/REAXYS Number:

104666

MDL number:

MFCD00005424

Assay:

98%

Form:

liquid

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Properties

assay

98%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.651 (lit.)

bp

73 °C/15 mmHg (lit.)

mp

−40 °C (lit.)

density

1.902 g/mL at 25 °C (lit.)

functional group

iodo

storage temp.

2-8°C

SMILES string

Ic1cccs1

InChI

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

InChI key

ROIMNSWDOJCBFR-UHFFFAOYSA-N

Description

General description

Mechanism of the fluoride-free, palladium-catalyzed cross-coupling reaction of 2-iodothiophene with potassium (E)-heptenyldimethylsilanolate has been investigated. 2-Iodothiophene participates in microwave-enhanced, rapid homogeneous-phase version of the Sonogashira reaction.

Application

2-Iodothiophene was used in the synthesis of (E)-and (Z)-2,3-difluoro-3-aryl substituted acrylic esters. It was also used as monomer in the preparation of thin conductive films via plasma polymerization of 2-iodothiophene.

pictograms

GHS05,GHS07

signalword

Danger

hcodes

H302,H315,H317,H318,H335

pcodes

P261 - P280 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

170.6 °F - closed cup

flash_point_c

77 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating.

M Erdélyi et al.

The Journal of organic chemistry, 66(12), 4165-4169 (2001-06-09)

A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with trimethylsilylacetylene. Excellent yields (80-95%)

Thin conductive coatings formed by plasma polymerization of 2-iodothiophene.

Kruse A, et al.

Surface and Coatings Technology, 59(1), 359-364 (1993)

Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis.

Scott E Denmark et al.

Journal of the American Chemical Society, 126(15), 4876-4882 (2004-04-15)

The mechanism of the fluoride-free, palladium-catalyzed cross-coupling reaction of potassium (E)-heptenyldimethylsilanolate, K(+)(E)-1(-), with 2-iodothiophene has been investigated through kinetic analysis. The order of each component was determined by plotting the initial rates of the reaction against concentration. These data provided

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Global Trade Item Number

SKU	GTIN
196150-25G	04061838761910