391115
N-(Phenylthio)phthalimide
98%
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About This Item
Empirical Formula (Hill Notation):
C14H9NO2S
CAS Number:
Molecular Weight:
255.29
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
InChI
1S/C14H9NO2S/c16-13-11-8-4-5-9-12(11)14(17)15(13)18-10-6-2-1-3-7-10/h1-9H
SMILES string
O=C1N(Sc2ccccc2)C(=O)c3ccccc13
InChI key
NMHKBABHRKQHOL-UHFFFAOYSA-N
assay
98%
mp
160-163 °C (lit.)
solubility
DMSO: soluble 25 mg/mL, clear, yellow
General description
N-(Phenylthio)phthalimide is an N-substituted phthalimide. It is used as a sulphenylating agent. The synthesis of N-(phenylthio)phthalimide has been reported.
Application
N-(Phenylthio)phthalimide is suitable reagent used in the synthesis of phenyl (3-trimethoxysilylpropyl)-disulfide. It may be used in the sulfenylation of ylides and β−keto esters.
N-(Phenylthio)phthalimide may be used as sulfenylating agent in the synthesis of the following:
N-(Phenylthio)phthalimide may be used as sulfenylating agent in the synthesis of the following:
- α-phenylthio-ketones and α-phenylthio-aldehydes from aldehydes and ketones
- 3-sulfenyl indoles from indoles
- optically active 3-phenylthiooxindoles from unprotected 3-substituted oxindoles
- N−alkyl-β-phenylsulfenyl-2-acetylbenzimidazole from N−alkyl−2−acetylbenzimidazole
- N−phenylsulfenyl ketimines from oximes or nitro compounds
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Direct, organocatalytic α-sulfenylation of aldehydes and ketones.
Wang W, et al.
Tetrahedron Letters, 45(44), 8229-8231 (2004)
The use of anhydrous CeCl3 as a catalyst for the synthesis of 3-sulfenyl indoles.
Silveira CC, et al.
Tetrahedron Letters, 51(15), 2014-2016 (2010)
Jordi Burés et al.
Organic letters, 9(22), 4635-4638 (2007-10-09)
As N-sulfenyl imines (e.g., RR'C=N-SAr) can be readily transformed to their N-sulfinyl imines (RR'C=N-SOAr), N-sulfonyl imines (RR'C=N-SO2Ar), and N-sulfonyl oxaziridines, the very mild procedure developed to convert ketoximes and secondary nitro derivatives to N-arenesulfenyl ketimines constitutes a new and efficient
On the involvement of lipoic acid in. alpha.-keto acid dehydrogenase complexes.
Rastetter WH, et al.
Journal of the American Chemical Society, 101(10), 2752-2753 (1979)
Indium chloride: a versatile Lewis acid catalyst for the synthesis of 3-sulfenylindoles.
Kumar PP, et al.
Journal of Sulfur Chemistry, 35(4), 356-361 (2014)
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