939633
Indoline-2-thione
≥-95%
Synonym(s):
2,3-Dihydro-1H-indole-2-thione
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About This Item
Empirical Formula (Hill Notation):
C8H7NS
CAS Number:
Molecular Weight:
149.21
MDL number:
UNSPSC Code:
12352100
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Quality Level
assay
≥-95%
form
powder or crystals
reaction suitability
reaction type: Photocatalysis
color
white to yellow
SMILES string
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)
InChI key
IGJWTYFTQNHSEK-UHFFFAOYSA-N
General description
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
- The synthesis of thioethers from aryl chlorides & alcohols
Features and Benefits
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.
related product
Product No.
Description
Pricing
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
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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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