17101-98-3

Basic information

• Product Name: Carbamic acid, [(4-methylphenyl)methyl]-, ethyl ester
• CAS NO: 17101-98-3
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Mol File: 17101-98-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(4-methylphenyl)methyl]-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(4-methylphenyl)methyl]-, ethyl ester(17101-98-3)
• EPA Substance Registry System: Carbamic acid, [(4-methylphenyl)methyl]-, ethyl ester(17101-98-3)

Safety Data

• Hazardous Substances Data: 17101-98-3(Hazardous Substances Data)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 104-84-7 para-methylbenzylamine 
• 64-17-5 ethanol 
• 263746-53-8 O-ethyl-S-(4-bromophenyl)thiocarbonate 
• 78725-88-9 O-ethyl S-(4-methylphenyl) thiocarbonate 
• 107701-35-9 O-ethyl S-(4-chlorophenyl) thiocarbonate 
• 78725-90-3 S-phenyl-O-ethyl thiolcarbonate 
• 22719-89-7 ethyl m-nitrophenyl carbonate 
• 22719-86-4 1-(4-ethoxycarbonyloxy-phenyl)-ethanone 
• 6132-45-2 ethyl 4-nitrophenyl carbonate 
• 622-47-9 4-tolylacetic acid 

Downstream Products

• 41789-95-1 1-(3-methoxyphenyl)-N-methylmethanamine 
• 699-04-7 N-methyl-p-methylbenzylamine 

Relevant articles and documents

Urethanes synthesis from oxamic acids under electrochemical conditions

Urethane synthesis via oxidative decarboxylation of oxamic acids under mild electrochemical conditions is reported. This simple phosgene-free route to urethanes involves an in situ generation of isocyanates by anodic oxidation of oxamic acids in an alcoholic medium. The reaction is applicable to a wide range of oxamic acids, including chiral ones, and alcohols furnishing the desired urethanes in a one-pot process without the use of a chemical oxidant.

Preparation and applications of a polymer-supported phosphoryl azide

A polymer-supported diphenylphosphoryl azide was prepared. This polymer-supported version of DPPA is useful due to its lower toxicity, moisture tolerance and ease of workup after reaction. The synthetic application of this solid-phase reagent was explored by conversion of a variety of carboxylic acids to urethanes and ureas through Curtius rearrangement reactions. Carboxylic acids bearing different functional groups (aromatic, aliphatic and heterocyclic carboxylic acids) were subjected to the reaction. The corresponding products were isolated with satisfactory yields.

Kinetics and mechanism of the aminolysis of ethyl aryl carbonates in acetonitrile

The aminolysis reactions of ethyl aryl carbonates with benzylamines in acetonitrile at 25.0°C are investigated. The base-catalyzed path, k2, disappears when strong nucleophiles (X = p-CH3O and p-CH3) react with a substrate activated by a strong nucleofuge (Z = p-NO2). The large magnitude of ρ(x) (-1.7 to -2.5), ρ(z) (3.4 to 4.3), and ρ(xz) (1.4) values, and relatively large k(H)/k(D) (1.6 to 1.8) found for the uncatalyzed path (k1) can be accounted for in terms of a stepwise mechanism with rate-limiting expulsion of the phenoxide leaving group. The catalyzed process (k2) is characterized by the much smaller magnitude of ρ(x) (-1.0 to -1.7), ρ(z) (0.4 to 0.7), and ρ(xz) (0.2), the larger k(H)/k(D) (2.1 to 2.5) values, and the lower ΔH(+) values (1.8-1.9 kcal mol-1) than those of the uncatalyzed process (k1) with large negative ΔS(+) values (-65 to -67 cal K-1 mol- 1). These results are consistent with four- and six-centered transition states for the two processes, k1 and k2, respectively.