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254614

Sigma-Aldrich

N-(Phenylseleno)phthalimide

technical grade

Synonym(s):

2-(Phenylseleno)-1H-isoindole-1,3(2H)-dione, 2-Phenylselanylisoindole-1,3-dione, N-Phenylselenylphthalimide

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About This Item

Empirical Formula (Hill Notation):
C14H9NO2Se
CAS Number:
71098-88-9
Molecular Weight:
302.19
MDL number:
MFCD00010406
UNSPSC Code:
12352100
PubChem Substance ID:
24855397
NACRES:
NA.22

grade

technical grade

mp

181-184 °C (lit.)

functional group

imide

storage temp.

−20°C

SMILES string

O=C1N([Se]c2ccccc2)C(=O)c3ccccc13

InChI

1S/C14H9NO2Se/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

TYZFQSLJTWPSDS-UHFFFAOYSA-N

Application

N-(Phenylseleno)phthalimide is a versatile selenamide reagent and has been used:
  • to selectively derivatize thiols for mass spectrometric analysis
  • to derivatize thiol peptides in protein digests
  • in L-prolinamide or pyrrolidine trifluoromethanesulfonamide promoted α-selenenylation reactions of aldehydes and ketones
  • for introducing PhSe into protected glycals, ketones, aldehydes, stannanes and exocyclic alkenes

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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Synlett, 419-419 (1992)
Tetrahedron Letters, 34, 7755-7755 (1993)
Tetrahedron Letters, 33, 6243-6243 (1992)
Tetrahedron Letters, 34, 7915-7915 (1993)
Jian Wang et al.
The Journal of organic chemistry, 70(14), 5678-5687 (2005-07-02)
[reaction: see text] A new catalytic method for direct alpha-selenenylation reactions of aldehydes and ketones has been developed. The results of exploratory studies have demonstrated that L-prolinamide is an effective catalyst for alpha-selenenylation reactions of aldehydes, whereas pyrrolidine trifluoromethanesulfonamide efficiently
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