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2‐Indolinethione
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image
[496‐30‐0]
C
8
H
7
NS
(MW 149.21)
InChI =
1S/C8H7NS/c10‐8‐5‐6‐3‐1‐2‐4‐7(6)9‐8/h1‐4H,5H2,(H,9,10)
InChIKey =
IGJWTYFTQNHSEK‐UHFFFAOYSA‐N
(reagent used as a highly reducing photocatalyst,
1,2
for the synthesis of indole‐fused heterocycles
3
and as an
S
‐alkylating/arylation agent)
Alternative Names:
indolin‐2‐thione, indoline‐2‐thione, indole‐2‐thione, 1,3‐dihydro‐2
H
‐indole‐2‐thione, 1,3‐dihydroindole‐2‐thione.
Physical Data:
mp 144–147 °C
4
, p
K
a
= 10 in DMSO.
5
Solubility:
soluble in CH
2
Cl
2
, CH
3
CN, DMF, NMP, DMSO, CHCl
3
, acetone, EtOAc but insoluble in H
2
O and hexane.
Form Supplied in:
yellow solid; limited commercial availability.
Analysis of Reagent Purity:
NMR,
2,4
IR,
6
MS,
7
UV–Vis.
8
Preparative Methods:
synthesized from 2‐oxindole with either Lawesson's reagent in toluene
2
or P
4
S
10
in THF, followed by the addition of NaHCO
3
.
4
Purification:
by column chromatography on silica
2
or by precipitation with water.
4
Handling, Storage, and Precautions:
a bench‐stable solid that does not require special storage precautions. In solution, slow oxidation by oxygen may occur depending on the solvent, though it exhibits good stability in EtOH under aerobic conditions.
9
Under acidic or basic conditions, indoline‐2‐thione is more sensitive to oxidation, so an inert atmosphere is preferable. Decomposition to indole under UV irradiation has also been reported.
8,10
Title: 2‐Indolinethione
Description:
image
[496‐30‐0]
C
8
H
7
NS
(MW 149.
21)
InChI =
1S/C8H7NS/c10‐8‐5‐6‐3‐1‐2‐4‐7(6)9‐8/h1‐4H,5H2,(H,9,10)
InChIKey =
IGJWTYFTQNHSEK‐UHFFFAOYSA‐N
(reagent used as a highly reducing photocatalyst,
1,2
for the synthesis of indole‐fused heterocycles
3
and as an
S
‐alkylating/arylation agent)
Alternative Names:
indolin‐2‐thione, indoline‐2‐thione, indole‐2‐thione, 1,3‐dihydro‐2
H
‐indole‐2‐thione, 1,3‐dihydroindole‐2‐thione.
Physical Data:
mp 144–147 °C
4
, p
K
a
= 10 in DMSO.
5
Solubility:
soluble in CH
2
Cl
2
, CH
3
CN, DMF, NMP, DMSO, CHCl
3
, acetone, EtOAc but insoluble in H
2
O and hexane.
Form Supplied in:
yellow solid; limited commercial availability.
Analysis of Reagent Purity:
NMR,
2,4
IR,
6
MS,
7
UV–Vis.
8
Preparative Methods:
synthesized from 2‐oxindole with either Lawesson's reagent in toluene
2
or P
4
S
10
in THF, followed by the addition of NaHCO
3
.
4
Purification:
by column chromatography on silica
2
or by precipitation with water.
4
Handling, Storage, and Precautions:
a bench‐stable solid that does not require special storage precautions.
In solution, slow oxidation by oxygen may occur depending on the solvent, though it exhibits good stability in EtOH under aerobic conditions.
9
Under acidic or basic conditions, indoline‐2‐thione is more sensitive to oxidation, so an inert atmosphere is preferable.
Decomposition to indole under UV irradiation has also been reported.
8,10.