22815-63-0

Basic information

• Product Name: N-^t-butyl benzylcarbamate
• Synonyms: N-^t-butyl benzylcarbamate
• CAS NO: 22815-63-0
• Molecular Weight: 207.272
• Mol File: 22815-63-0.mol

Chemical Properties

• CAS DataBase Reference: N-^t-butyl benzylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: N-^t-butyl benzylcarbamate(22815-63-0)
• EPA Substance Registry System: N-^t-butyl benzylcarbamate(22815-63-0)

Safety Data

• Hazardous Substances Data: 22815-63-0(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 75-98-9 Trimethylacetic acid 
• 124-38-9 carbon dioxide 
• 100-44-7 benzyl chloride 
• 75-64-9 tert-butylamine 
• 501-53-1 benzyl chloroformate 
• 754-10-9 2,2-dimethylpropionamide 
• 1609-86-5 Tert-butyl isocyanate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 507-19-7 t-butyl bromide 
• 621-84-1 O-benzyl carbamate 
• 691-64-5 di-tert-butyl oxalate 
• 69777-55-5 tert-butyl(morpholin-2-ylmethyl)carbamate 
• 119072-55-8 tert-butylisonitrile 

Downstream Products

• 15942-15-1 N-benzyl-N'-tert-butyl urea 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 126404-91-9 tert-Butyl-carbamic acid 2-hydroxy-1,2-diphenyl-ethyl ester 
• 126404-99-7 tert-Butyl-carbamic acid 1-methyl-1,2-diphenyl-ethyl ester 
• 126404-89-5 tert-Butyl-carbamic acid 5-chloro-1-phenyl-pentyl ester 
• 126404-95-3 tert-Butyl-carbamic acid 4-bromo-1-phenyl-pentyl ester 
• 126404-93-1 tert-Butyl-carbamic acid 2-hydroxy-4-iodo-3,3-dimethyl-1-phenyl-butyl ester 
• 126404-88-4 tert-Butyl-carbamic acid 4-chloro-1-phenyl-butyl ester 
• 126404-84-0 tert-Butyl-carbamic acid 1,2-diphenyl-ethyl ester 
• 126404-86-2 tert-Butyl-carbamic acid 3-chloromethyl-1-phenyl-but-3-enyl ester 
• 126405-01-4 tert-Butyl-carbamic acid 4-chloro-1-methyl-1-phenyl-butyl ester 
• 126404-87-3 tert-Butyl-carbamic acid (E)-5-chloro-1-phenyl-pent-3-enyl ester 
• 126404-98-6 tert-Butyl-carbamic acid 1-phenyl-1-trimethylsilanyl-ethyl ester 
• 126404-90-8 tert-Butyl-carbamic acid phenyl-trimethylsilanyl-methyl ester 

Relevant articles and documents

Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds

We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.

Organic photoredox catalyst with substrate-capture ability: A perylene derivative bearing urethane moiety for reductive coupling of ketones and aldehydes under visible light

A perylene derivative bearing a urethane moiety served as an efficient photoredox catalyst for the reductive coupling of ketones and aldehydes under visible light, implicating that the urethane moiety captured substrates through hydrogen bonds to lower the LUMO levels of the captured substrates, thus promoting single electron transfer from the reductant anion radical of the perylene moiety to the substrates.

A Simple, efficient, Catalyst-Free and Solvent-Less Microwave-Assisted process for N-Cbz Protection of Several amines

A simple, green and chemo-selective method for the N-benzyloxycarbonylation of amines, β-amino alcohols, α-amino esters and sulfonamides has been developed under microwave irradiation. Good to excellent yields of the N-benzyloxy-carbamates compounds were obtained in short times without any side products.

Oximes as reusable templates for the synthesis of ureas and carbamates by an: In situ generation of carbamoyl oximes

Oximes have been identified as reusable templates for the synthesis of ureas and carbamates by an in situ generation of carbamoyl oximes under metal-free conditions. The recovered oxime has been utilised for three trials in the synthesis of urea derivatives without any loss in the yield and efficiency. In addition, this template approach could override the usage of hazardous and less stable isocyanates as substrates.

A high-yielding, expeditious, and multicomponent synthesis of urea and carbamate derivatives by using triphenylphosphine/trichloroisocyanuric acid system

An efficient method for the synthesis of urea and carbamate derivatives from amines and alcohols is described by using triphenylphosphine (PPh3)/trichloroisocyanuric acid system. The protocol allows for the preparation of symmetrical, unsymmetrical di, tri-, and tetra-substituted ureas and carbamates and is tolerant of a wide range of functional groups. To optimize the reaction conditions, experimental variables including temperature, the concentration of amine and alcohol, solvent, and reaction time were studied. Satisfactory yields were obtained at the optimized conditions. The present methodology is experimentally simple, mild, and represents a valuable alternative to the existing methods.

Synthesis, X-ray crystallography, and reactions of N-acyl and N-carbamoyl succinimides

A collection of N-acyl and N-carbamoyl succinimides were prepared by acylation of succinimide with acyl chlorides or by ethylene dichloride (EDC) coupling of carboxylic acids. The x-ray crystal structures of N-benzoyl and N-p-nitrobenzoyl succinimides were determined. The N-acyl succinimides were effective in acylating primary amines, a secondary amine, and an aromatic amine. Copyright

BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional hetercyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

Chemoselective alkoxycarbonylation reagent having trifluoromethylsulfonyl-4-trifluoromethylanilide as a leaving group

N-Benzyloxy- and N-tert-butoxycarbonyltrifluoromethylsulfonyl-4-trifluoromethylanilides were prepared and were found to be chemoselective and shelf-storable alkoxycarbonylation reagents.

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.

Highly Selective Generation of Urethanes from Amines, Carbon Dioxide and Alkyl Chlorides

Generation of carbamate anions from either a primary or secondary amine, carbon dioxide and a stoichiometric amount of a pentaalkylguanidine followed by the addition of alkyl chlorides gives high yields of urethanes.