287729-06-0

Basic information

• Product Name: Carbamic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl-, phenylmethyl ester
• CAS NO: 287729-06-0
• Molecular Formula: C17H14N2O4
• Molecular Weight: 310.309
• Mol File: 287729-06-0.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl-, phenylmethyl ester(287729-06-0)
• EPA Substance Registry System: Carbamic acid, (1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl-, phenylmethyl ester(287729-06-0)

Safety Data

• Hazardous Substances Data: 287729-06-0(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 287728-91-0 N-benzyloxycarbonylaminophthalimide 
• 74-88-4 methyl iodide 
• 85-44-9 phthalic anhydride 
• 5331-43-1 N-benzyloxycarbonyl-hydrazine 

Downstream Products

• 426840-24-6 N^α-(benzyloxycarbonyl)-N^β,N^β-bis(tert-butyloxycarbonyl)-N^α-methylhydrazine 
• 127799-53-5 1-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)carbonyl]-2-methylhydrazine 
• 37519-04-3 1-(benzyloxy)carbonyl-1-methylhydrazine 

Relevant articles and documents

Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches

Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N-aminophthalimide derivatives can be efficiently converted into the corresponding N-amino-imidodicarbonates by a three-stage, one-flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ -diprotected α-hydrazino esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Use of N-acyl or N-alkyloxycarbonyl-aminotetrachlorophthalimides for the preparation of alkylhydrazines via the mitsunobu protocol

N-acyl and N-alkyloxycarbonyl tetrachloro-aminophthalimides which are best acidic partners in the Mitsunobu reaction and more easily dephthaloylated than their unsubstituted analogs can be used efficiently for the preparation of 1,1-substituted hydrazines.

New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol

N-acyl- and N-alkoxycarbonylaminophthalimides are prepared using a convenient reaction and are efficiently used as acid partners in Mitsunobu reaction. This reaction allows them to be alkylated by primary, secondary or benzyl groups. Comparison of the reactivities and pKa values of these N-substituted aminophthalimides suggest that the success of the Mitsunobu reaction in this case seems to be governed more by steric than by electronic effects. A final dephthaloylation step results in an efficient method for the preparation of 1,1-substituted hydrazines.