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939633

Sigma-Aldrich

Indoline-2-thione

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greener alternative

≥-95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H7NS
CAS Number:
496-30-0
Molecular Weight:
149.21
MDL number:
MFCD09971323
UNSPSC Code:
12352100

Quality Level

100

Assay

≥-95%

form

powder or crystals

reaction suitability

reaction type: Photocatalysis

greener alternative product characteristics

Catalysis
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Greener Alternative Product

color

white to yellow

greener alternative category

Aligned

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

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

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

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.

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Description
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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000388838
0000388837
0000366308
0000388837
0000388838

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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
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
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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