Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

391115

Sigma-Aldrich

N-(Phenylthio)phthalimide

98%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C14H9NO2S
CAS Number:
14204-27-4
Molecular Weight:
255.29
MDL number:
MFCD00192396
UNSPSC Code:
12352100
PubChem Substance ID:
24864360

Assay

98%

mp

160-163 °C (lit.)

solubility

DMSO: soluble 25 mg/mL, clear, yellow

SMILES string

O=C1N(Sc2ccccc2)C(=O)c3ccccc13

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

InChI key

NMHKBABHRKQHOL-UHFFFAOYSA-N

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:
  • 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

391115-VAR:
391115-BULK:
391115-5G:
391115-25G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
18503BZ
12916CU

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Direct, organocatalytic α-sulfenylation of aldehydes and ketones.
Wang W, et al.
Tetrahedron Letters, 45(44), 8229-8231 (2004)
Asymmetric phase-transfer reactions under base-free neutral conditions.
Shirakawa S and Maruoka K.
Tetrahedron Letters, 55(29), 3833-3839 (2014)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service