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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

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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.

PDSCL

Poisonous substance

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

254614-VAR:
254614-1G:4548173125190
254614-5G:4548173125213
254614-250MG:4548173125206
254614-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
0000225674
0000231121
0000231149
MKBD7898
MKBF2828

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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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