99075-91-9

Basic information

• Product Name: methyl N-(4'-methoxybenzyl)carbamate
• Synonyms: methyl N-(4'-methoxybenzyl)carbamate
• CAS NO: 99075-91-9
• Molecular Weight: 195.218
• Mol File: 99075-91-9.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl N-(4'-methoxybenzyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(4'-methoxybenzyl)carbamate(99075-91-9)
• EPA Substance Registry System: methyl N-(4'-methoxybenzyl)carbamate(99075-91-9)

Safety Data

• Hazardous Substances Data: 99075-91-9(Hazardous Substances Data)

Upstream product

• 6343-93-7 2-(4-methoxyphenyl)acetamide 
• 67-56-1 methanol 
• 56651-60-6 4-methoxybenzyl isocyanate 
• 65398-61-0 O-methyl S-p-bromophenyl thiocarbonate 
• 2393-23-9 4-methoxy-benzylamine 
• 3186-52-5 O-methyl-S-phenyl thiolcarbonate 
• 3186-65-0 O-methyl S-p-chlorophenyl thiocarbonate 
• 3186-53-6 O-methyl S-p-methylphenyl thiocarbonate 
• 87721-45-7 (4-Methoxy-phenyl)-acetyl azide 
• 123-11-5 4-methoxy-benzaldehyde 
• 598-55-0 methyl carbamate 
• 100-46-9 benzylamine 
• 79-22-1 methyl chloroformate 

Downstream Products

• 2393-23-9 4-methoxy-benzylamine 
• 67-56-1 methanol 
• 243636-61-5 N-but-2-enyl-N-(4-methoxy-benzyl)-malonamic acid methyl ester 
• 243636-71-7 (E)-N-(4-methoxybenzyl)but-2-en-1-amine 
• 348620-16-6 methyl N-crotyl-N-(4'-methoxybenzyl)malonylamide 
• 348620-09-7 N-(4-methoxybenzyl)but-2-en-1-amine 
• 243636-76-2 diethyl N-{4-[2-(2-amino-3,4-dihydro-4-oxo-7-(4'-methoxybenzyl)pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamate 
• 348620-53-1 2-amino-4-oxo-5-vinyl-7-(4'-methoxybenzyl)-3,4,5,6-tetrahydropyrrolo[2,3-d]pyrimidine 
• 348620-42-8 1-(4'-methoxybenzyl)-3-methoxycarbonyl-4-vinyl-2-pyrrolidinethione 
• 348620-03-1 methyl N-crotyl-N-(4'-methoxybenzyl)carbamate 
• 243637-18-5 ((E)-But-2-enyl)-(4-methoxy-benzyl)-carbamic acid methyl ester 
• 152898-96-9 C₁₅H₂₁NO₅ 

Relevant articles and documents

Iodoarene-catalyzed oxidative transformations using molecular oxygen

Molecular oxygen serves as a useful oxidant for the glycol scission of 1,2-diols and the Hofmann rearrangement of primary amides using pentamethyliodobenzene as a catalyst. The use of isobutyraldehyde and Lewis basic nitriles under O2 enabled the iodine(i)/(iii) catalytic cycle, where in situ-generated peracid acts as a terminal oxidant.

Kinetics and mechanism of the aminolysis of O-methyl S-aryl thiocarbonates in acetonitrile

The aminolysis of O-methyl S-aryl thiocarbonates with benzylamines are studied in acetonitrile at -45.0°C. The βX (βnuc) values are in the range 0.62-0.80 with a negative cross-interaction constant, ρXZ = -0.42, which are interpreted to indicate a concerted mechanism. The kinetic isotope effects involving deuterated benzylamine nucleophiles (XC6H 4CH2ND2) are large, kH/kD = 1.29-1.75, suggesting that the N-H(D) bond is partially broken in the transition state by forming a hydrogen-bonded four-center cyclic structure. The concerted mechanism is enforced by the strong push provided by the MeO group which enhances the nucleofugalities of both benzylamine and arenethiolate from the putative zwitterionic tetrahedral intermediate.

Facile preparation of protected benzylic and heteroarylmethyl amines via room temperature Curtius rearrangement

A step-wise, room temperature procedure for acyl azide formation and the subsequent Curtius rearrangement of phenyl and heteroaryl acetic acids is described. We have developed a protocol for room temperature Curtius rearrangement in MeOH or CHCl3 that provides an improvement over standard conditions, avoiding the use of additives or heat. This room temperature optimization of the Curtius rearrangement prevents the formation of side products often observed with benzylic acids, allowing access to a variety of benzylic and heteroarylmethyl amines.