285119-75-7

Basic information

• Product Name: Carbamic acid, [4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-, 1,1-dimethylethyl ester
• Synonyms: [4-(tert-butoxycarbonylaminomethyl)phenyl]carbamic acid tert-butyl ester
• CAS NO: 285119-75-7
• Molecular Formula: C17H26N2O4
• Molecular Weight: 322.404
• Mol File: 285119-75-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-, 1,1-dimethylethyl ester(285119-75-7)
• EPA Substance Registry System: Carbamic acid, [4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-, 1,1-dimethylethyl ester(285119-75-7)

Safety Data

• Hazardous Substances Data: 285119-75-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4403-71-8 (4-aminomethyl)aniline 
• 619-72-7 4-nitrobenzonitrile 

Downstream Products

• 926-05-6 tert-butyl nitrate 
• 4403-71-8 (4-aminomethyl)aniline 
• 220298-96-4 4‐(tert‐butoxycarbonylamino)benzylamine 
• 94838-55-8 tert-butyl (4-aminobenzyl)carbamate 

Relevant articles and documents

Nonsolvent application of ionic liquids: Organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency

1-Alkyl-3-methylimidazolium cation based ionic liquids efficiently catalyze N-tert-butyloxycarbonylation of amines with excellent chemoselectivity. The catalytic role of the ionic liquid is envisaged as "electrophilic activation" of di-tert-butyl dicarbonate (Boc2O) through bifurcated hydrogen bond formation with the C-2 hydrogen of the 1-alkyl-3-methylimidazolium cation and has been supported by a downfield shift of the imidazolium C-2 hydrogen of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2]) from δ 8.39 to 8.66 in the presence of Boc2O in the 1H NMR and a drastic reduction of the catalytic efficiency with 1-butyl-2,3-dimethylimidazolium ionic liquids that are devoid of the C-2 hydrogen. The differential time required for reaction with aromatic and aliphatic amines has offered means for selective N-t-Boc formation during inter and intramolecular competitions. Preferential N-t-Boc formation with secondary aliphatic amine has been achieved in the presence of primary aliphatic amine. Comparison of the catalytic efficiency for N-t-Boc formation with a common substrate revealed that [bmim][NTf2] is superior to the reported Lewis acid catalysts.

Selective nitrolytic deprotection of N-BOC-amines and N-BOC-amino acids derivatives

The extension of the deprotection procedure using HNO3 in CH2Cl2 to a number of appropriately selected N-BOC-masked amines and derivatives of natural amino acids was investigated. The method was found to work effectively with almost all tested substrates, with the exception of activated aromatic amines and heterocycles which underwent unavoidable faster oxidation. Alanine, phenylalanine, serine and lysine derivatives were efficiently deprotected, as well as dipeptide Ala-Phe, preserving the configuration of the substrates and without affecting copresent Z and ester functions, with a remarkable selectivity towards acid sensitive t-butyl esters. The obtained amino acids esters, isolated and characterized in the form of nitrates salts, proved to be suitable intermediates to be used in peptide synthesis.