939641
1-Methylindoline-2-thione
≥95%, powder or crystals
Synonym(s):
1-Methyl-2,3-dihydro-1H-indole-2-thione
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About This Item
Empirical Formula (Hill Notation):
C9H9NS
CAS Number:
Molecular Weight:
163.24
MDL number:
NACRES:
NA.21
Product Name
1-Methylindoline-2-thione, ≥95%
Quality Level
Assay
≥95%
form
powder or crystals
reaction suitability
reaction type: Photocatalysis
greener alternative product characteristics
Catalysis
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color
white to yellow
greener alternative category
SMILES string
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
Related Categories
General description
1-Methylindoline-2-thione is a indole thiolate often used in the synthesis of (Indoline-2-S) related products.
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Application
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
- The activation of C-F. C-Cl and C-O bonds
- 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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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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.
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
N-Alkylated Analogues of Indolylthio Glycosides as Glycosyl Donors with Enhanced Activation Profile.
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
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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