93378-90-6

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylseleno)methyl]-
• CAS NO: 93378-90-6
• Molecular Formula: C15H11NO2Se
• Molecular Weight: 316.218
• Mol File: 93378-90-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylseleno)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylseleno)methyl]-(93378-90-6)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-[(phenylseleno)methyl]-(93378-90-6)

Safety Data

• Hazardous Substances Data: 93378-90-6(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 71098-88-9 N-phenylselanylphthalimide 
• 17564-64-6 N-(chloromethyl)phthalimide 
• 645-96-5 Benzeneselenol 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 54399-24-5 2-<(cyclohexyloxy)methyl>-isoindole-1,3(2H)-dione 
• 1373155-09-9 C₂₀H₂₂N₂O₅S 

Relevant articles and documents

O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.

INSERION REACTIONS OF DIAZO COMPOUNDS WITH SOME SELENIUM(II) ELECTROPHILES

Benzene- and o-nitrobenzene-selenyl thiocyanate (1 and 2) reacted with diazomethane and several α-diazo esters to afford α-arylseleno isothiocyanates (5a-10a) and the isomeric thiocyanates (6b-8b) as the major and minor products, respectively.Analogous insertion reactions were observed with benzenesulfenyl thiocyanate (3) and benzeneselenenyl selenocyanate (4) to furnish phenylthiomethyl isothiocyanate (11), ethyl α-phenylthioisocyanoacetate (12) and phenylselenomethyl isoselelnocyanate (13), ethyl α-phenylseleno-α-isoselenocyanoacetate (14), respectively.N-(Phenylseleno)phthalimide formed insertion products N-(phenylselenomethyl)phthalimide (16) and ethyl α-phenylseleno-α-phthalimidoacetate (17)with diazomethane and ethyl diazoacetate, but effected elimination to the corresponding vinyl selenides, ethyl α-(phenylseleno)propenoate (18) and ethyl 2-phenylseleno-3-methyl-2-butenoate (19) when treated with diazo esters containing β-hydrogens.Compound 19 was similarly obtained from benzeneselenenyl iodide and the diazo ester.Attempts to effect selenoxide eliminations in compounds 7a-10a were unsuccessful.A new, efficient preparation of 1 from the metathesis of benzeneselenenyl chloride with trimethylsilyl isothiocyanate was developed.