6324-63-6

Basic information

• Product Name: dibenzyl benzene-1,4-diylbiscarbamate
• CAS NO: 6324-63-6
• Molecular Formula: C₂₂H₂₀N₂O₄
• Molecular Weight: 376.4052
• Mol File: 6324-63-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 487.4°C at 760 mmHg
• Flash Point: 248.5°C
• Density: 1.299g/cm³
• Vapor Pressure: 1.2E-09mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: dibenzyl benzene-1,4-diylbiscarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: dibenzyl benzene-1,4-diylbiscarbamate(6324-63-6)
• EPA Substance Registry System: dibenzyl benzene-1,4-diylbiscarbamate(6324-63-6)

Safety Data

• Hazardous Substances Data: 6324-63-6(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 106-50-3 1,4-phenylenediamine 
• 701-56-4 4-methoxy-N,N-dimethylanilne 
• 116015-91-9 N,N'-cyclohexa-2,5-diene-1,4-diylidene-bis-carbamic acid dibenzyl ester 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 124-38-9 carbon dioxide 
• 100-44-7 benzyl chloride 
• 121-69-7 N,N-dimethyl-aniline 
• 99-97-8 Dimethyl-p-toluidine 

Downstream Products

• 116015-97-5 (4-{Benzyloxycarbonyl-[(methyl-p-tolyl-amino)-methyl]-amino}-phenyl)-carbamic acid benzyl ester 
• 116015-99-7 [4-(Benzyloxycarbonyl-{[(4-chloro-phenyl)-methyl-amino]-methyl}-amino)-phenyl]-carbamic acid benzyl ester 

Relevant articles and documents

Carbon Dioxide as a Phosgene Replacement: Synthesis and Mechanistic Studies of Urethanes from Amines, CO2, and Alkyl Chlorides

Several carbamate esters were synthesized from amines, carbon dioxide, and alkyl chlorides.The effect of added base on the yield and selectivity of carbamate ester formation was found to be highly important with the use of sterically hindered guanidine bases giving the best results.Relative rate studies were carried out giving the following order of reactivity between carbamate anions in acetonitrile with benzyl chloride giving carbamate esters: Et2NCO2(-) = Bu2NCO2(-) > t-BuNHCO2(-) = CyNHCO2(-) = s-BuNHCO2(-) > PhNHCO2(-) > CyCH2NHCO2(-) = n-octylNHCO2(-) = n-BuNHCO2(-).Rate studies were carried out with the diethyl, s-butyl, phenyl, and n-butyl carbamates and activation parameters were determined to be Et2NCO2(-), ΔH(excit.) = 11.8 kcal/mol, ΔS(excit.) = -33 eu; s-BuNHCO2(-), ΔH(excit.) = 12.8 kcal/mol, ΔS(excit.) = -33 eu; PhNHCO2(-), ΔH(excit.) = 14.3 kcal/mol, ΔS(excit.) = -28 eu; n-BuNHCO2(-), ΔH(excit.) = 23.4 kcal/mol, ΔS(excit.) = -3 eu.The unusual results obtained from the use of n-BuNHCO2(-) prompted further studies which showed that the rate of the reaction was inversely dependent on carbon dioxide pressure (20 psig CO2, k = 4.84E-4 M-1 s-1; 120 psig CO2, k = 1.83E-4 M-1 s-1).Nitrogen NMR spectroscopy indicated, via a labeling study with 15N amines and 13C enriched carbon dioxide, the formation of doubly inserted product from the addition of two carbon dioxides to ethylamine in acetonitrile.

Reactions of p-Benzoquinone Diimine Derivatives with N,N-Dimethylanilines

N,N'-Bisalkoxycarbonyl-p-benzoquinone diimine underwent a thermal addition reaction with N,N-dimethylanilines to form an N-C bond between an imino group and an N-methyl group.Upon irradiation the reaction was accelerated.The reaction did not proceed with N-alkyl substituted anilines other than methyl.