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196150

Sigma-Aldrich

2-Iodthiophen

98%

Synonym(e):

α-Iodothiophene, 2-Thienyl iodide

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About This Item

Empirische Formel (Hill-System):
C4H3IS
CAS-Nummer:
3437-95-4
Molekulargewicht:
210.04
Beilstein:
104666
EG-Nummer:
222-342-1
MDL-Nummer:
MFCD00005424
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24851738
NACRES:
NA.22

Assay

98%

Form

liquid

Enthält

copper as stabilizer

Brechungsindex

n20/D 1.651 (lit.)

bp

73 °C/15 mmHg (lit.)

mp (Schmelzpunkt)

−40 °C (lit.)

Dichte

1.902 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

Ic1cccs1

InChI

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

InChIKey

ROIMNSWDOJCBFR-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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.

Piktogramme

CorrosionExclamation mark
GHS05,GHS07

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

170.6 °F - closed cup

Flammpunkt (°C)

77 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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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)
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
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
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

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