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Merck
CN

939641

Sigma-Aldrich

1-Methylindoline-2-thione

greener alternative

≥95%, powder or crystals

别名:

1-Methyl-2,3-dihydro-1H-indole-2-thione

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关于此项目

经验公式(希尔记法):
C9H9NS
化学文摘社编号:
分子量:
163.24
MDL编号:
NACRES:
NA.21
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产品名称

1-Methylindoline-2-thione, ≥95%

质量水平

方案

≥95%

表单

powder or crystals

反应适用性

reaction type: Photocatalysis

环保替代产品特性

Catalysis
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sustainability

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颜色

white to yellow

环保替代产品分类

SMILES字符串

S=C1N(C)C2=CC=CC=C2C1

InChI

InChI=1S/C9H9NS/c1-10-8-5-3-2-4-7(8)6-9(10)11/h2-5H,6H2,1H3

InChI key

GBSPZRWQIJCQQB-UHFFFAOYSA-N

相关类别

一般描述

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

1-Methylindoline-2-thione is a indole thiolate has been used in the synthesis of:
  • Brassilexin, Sinalexin and Wasalexins
  • Functionilized thiopyrano-indole annulated heterocycles
  • N-Alkylated Analogues of Indolylthio Glycosides
Also used as a photoreductant in:
  • The activation of C-F. C-Cl and C-O bonds
  • The synthesis of thioethers from aryl chlorides & alcohols

特点和优势

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.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Shuo Wu et al.
Angewandte Chemie (International ed. in English), 62(32), e202306364-e202306364 (2023-06-16)
Due to their strong covalent bonds and low reduction potentials, activating inert substrates is challenging. Recent advances in photoredox catalysis offered a number of solutions, each of which useful for activating specific inert bonds. Developing a general catalytic platform that
Ganesh Shrestha et al.
European journal of organic chemistry, 2022(18), e202200300-e202200300 (2022-11-08)
While studying indolylthio glycosides, previously we determined their activation profile that required large excess of activators. This drawback was partially addressed in the present study of N-alkylated SInR derivatives. The activation process was studied by NMR and the increased understanding
M Soledade C Pedras et al.
The Journal of organic chemistry, 70(5), 1828-1834 (2005-02-26)
Efficient syntheses of the phytoalexins brassilexin, sinalexin, and analogues are demonstrated through the application of the Vilsmeier formylation to indoline-2-thiones followed by a new aqueous ammonia workup procedure. Similarly, a very concise two-pot synthesis of the phytoalexins wasalexins using sequential
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
Xiang Chen et al.
Organic letters, 17(1), 42-45 (2014-12-18)
A formal thio [3 + 3]-cyclization catalyzed by a DPEN-derived chiral thiourea has been reported for the construction of optically active thiopyrano-indole annulated heterocyclic compounds in high yields with excellent enantioselectivities. The high reactivity between indoline-2-thione (keto-S) and 2-benzylidenemalononitrile has

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