2-(phenylselanyl)-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 145763
• Molecular Formular: C14H9NO2Se
• Molecular Mass: 302.18676
• Monoisotopic Mass: 302.97984953
• SMILES: c1ccc(cc1)[Se]N1C(=O)c2ccccc2C1=O
• Canonical SMILES: O=C1N([Se]c2ccccc2)C(=O)c2c1cccc2
• InChI: 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
• InChIKey: TYZFQSLJTWPSDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(phenylselanyl)-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-(phenylselanyl)isoindole-1,3-dione
• Synonyms: N-(Phenylseleno)phthalimide; N-苯硒基邻苯二甲酰胺; N-(苯硒基)邻苯二甲酰亚胺

Database IDs

• CAS Number: 71098-88-9
• MDL Number: MFCD00010406
• Beilstein Number: 1468701
• PubChem SID: 24855397; 162239965
• PubChem CID: 590397

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.4551
• LogD (pH = 7.4): 2.4551
• Log P: 2.4551
• Molar Refractivity: 77.104 cm^3
• Polarizability: 23.55366 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 181-184 °C(lit.); ca 180°C

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3283; UN3283
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H331-H373-H400-H410; H301-H331-H373-H410
• GHS Precautionary statements: P260-P261-P301+P310-P321-P405-P501A; P261-P273-P301 + P310-P311-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3283 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: tech. 85%
• Grade: technical grade
• Empirical Formula (Hill Notation): C14H9NO2Se

DETAILS

Sigma Aldrich - 254614

Packaging
1, 5 g in glass bottle
Application
Versatile reagent for introducing PhSe into protected glycals,1 ketones,2 aldehydes,2 stannanes,3 and exocyclic alkenes.4

REFERENCES

• Reagent for the oxy-selenation of alkenes in the presence of 2-3 equivalents of water and an acid catalyst: J. Am. Chem. Soc., 101, 3704 (1979). The trans-?-hydroxy selenide products are useful intermediates, e.g. in the synthesis of allylic alcohols by selenoxide elimination. In general, the reagent is superior to the corresponding halides in intramolecular cyclization reactions with unsaturated acids, urethanes, etc. Even suitably disposed ketones may undergo cyclization of the enol form, in the presence of SnCl₄: J. Chem. Soc., Chem. Commun., 1251, 1252 (1982):