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939633

Sigma-Aldrich

Indoline-2-thione

new

≥-95%

Synonyme(s) :

2,3-Dihydro-1H-indole-2-thione

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About This Item

Formule empirique (notation de Hill):
C8H7NS
Numéro CAS:
496-30-0
Poids moléculaire :
149.21
Numéro MDL:
MFCD09971323
Code UNSPSC :
12352100

Niveau de qualité

100

Pureté

≥-95%

Forme

powder or crystals

Capacité de réaction

reaction type: Photocatalysis

Couleur

white to yellow

Chaîne SMILES 

S=C1NC2=CC=CC=C2C1

InChI

InChI=1S/C8H7NS/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)

Clé InChI

IGJWTYFTQNHSEK-UHFFFAOYSA-N

Description générale

Indoline-2-thione is a indole thiolate often used in the synthesis of (Indoline-2-S) related products.

Application

Indoline-2-thione is a indole thiolate has been used in:
  • The MgI2-catalyzed nucleophilic ring opening of donor-acceptor cyclopropanes
  • The synthesis of indole-fused dihydrothiopyrano scaffolds via [3+3] annulations of donor-acceptor cyclopropanes
  • The preparation of 2-carboxylated thieno [2,3- b] indoles
Also used as a catalytic photoreductant in:
  • The synthesis of thioethers from aryl chlorides & alcohols

Caractéristiques et avantages

1-Methylindoline-2-thione is an affordable indole thiolate that is useful in general synthesis as well as the transition-metal free photocatalytic reduction of a range of strong polar C-F, C-O and C-Cl bonds.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

115169

Tetramethylthiourea, 98%

T15156

3,4,5,6-Tetrahydro-2-pyrimidinethiol, ≥99%

939633

Indoline-2-thione, ≥-95%

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number
0000388838
0000388837
0000366308
0000388838
0000388837

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Giacomo Mari et al.
Organic & biomolecular chemistry, 20(20), 4167-4175 (2022-05-10)
A metal-free strategy, alternative to the known complex cycloaddition reactions, towards 2-carboxylated thieno [2,3-b] indole derivatives has been successfully developed. The novel approach involves as starting materials easy accessible 1,2-diaza-1,3-dienes and indoline 2-thione and requires mild reaction conditions. Furthermore, the
Pan Tang et al.
The Journal of organic chemistry, 87(16), 10890-10901 (2022-08-03)
MgI2-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as easy-to-handle sulfur nucleophiles were investigated. A series of functionalized γ-indolylthio butyric acid derivatives were synthesized in good to excellent yields under mild reaction conditions. Furthermore, the thioether functionalized ring-opening products
Braj Gopal et al.
The Journal of organic chemistry, 88(1), 132-142 (2022-12-17)
A new methodology for the synthesis of N-haloindole-fused dihydrothiopyrano derivatives via (3 + 3)-annulation of donor-acceptor cyclopropanes (DACs) with indoline-2-thiones in the presence of Sc(OTf)3 as a Lewis acid catalyst has been developed. This protocol provides a variety of indole-fused
Shuo Wu et al.
Journal of the American Chemical Society, 146(5), 2907-2912 (2024-01-24)
Thioethers, often found in pharmaceuticals and natural compounds, typically involve metal cross-coupling reactions, high temperatures, and the use of disagreeable thiols for their synthesis. Here we present a straightforward, thiol-free organocatalytic protocol that uses mild conditions to stitch together inexpensive

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