254614

Sigma-Aldrich

N-(Phenylseleno)phthalimide

technical grade

Empirical Formula (Hill Notation):
C14H9NO2Se
CAS Number:
Molecular Weight:
302.19
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

grade

technical grade

Quality Level

mp

181-184 °C (lit.)

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

Packaging

1, 5 g in glass bottle

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3283 6.1 / PGII

WGK Germany

WGK 3

Tetrahedron Letters, 33, 6243-6243 (1992)
Tetrahedron Letters, 34, 7755-7755 (1993)
Synlett, 419-419 (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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