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196150

Sigma-Aldrich

2-Iodothiophene

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
Beilstein/REAXYS Number:
104666
EC Number:
222-342-1
MDL number:
MFCD00005424
UNSPSC Code:
12352100
PubChem Substance ID:
24851738
NACRES:
NA.22

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.)

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

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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

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

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_germany

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

Certificates of Analysis (COA)

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Barbara Marchetti et al.
The Journal of chemical physics, 142(22), 224303-224303 (2015-06-15)
Velocity map imaging methods, with a new and improved ion optics design, have been used to explore the near ultraviolet photodissociation dynamics of gas phase 2-bromo- and 2-iodothiophene molecules. In both cases, the ground (X) and spin-orbit excited (X*) (where
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)
Yi Wang et al.
The Journal of organic chemistry, 70(26), 10743-10746 (2005-12-17)
[reaction: see text] The (Z)-2,3-difluoro-3-stannylacrylic ester is readily prepared from (Z)-1,2-difluorovinyltriethylsilane via stereospecific stannyl/silyl exchange with KF/(Bu3Sn)2O or Bu3SnCl in DMF at 70 degrees C. The corresponding (E)-2,3-difluoro-3-stannylacrylate is prepared by stereospecific carbonylation of (E)-1,2-difluorovinyl iodide followed by low temperature/in
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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