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Merck
CN

939633

Indoline-2-thione

greener alternative

≥-95%, powder or crystals

别名:

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

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经验公式(希尔记法):
C8H7NS
化学文摘社编号:
分子量:
149.21
MDL number:
NACRES:
NA.21
Assay:
≥-95%
Form:
powder or crystals
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产品名称

Indoline-2-thione, ≥-95%

InChI key

IGJWTYFTQNHSEK-UHFFFAOYSA-N

InChI

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

SMILES string

S=C1NC2=CC=CC=C2C1

assay

≥-95%

form

powder or crystals

reaction suitability

reaction type: Photocatalysis

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

color

white to yellow

greener alternative category

Quality Level

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

Indoline-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.

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

法规信息

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分析证书(COA)

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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
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
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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