28685-60-1

Basic information

• Product Name: Carbamic acid, methylphenyl-, methyl ester
• CAS NO: 28685-60-1
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Mol File: 28685-60-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: Carbamic acid, methylphenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, methylphenyl-, methyl ester(28685-60-1)
• EPA Substance Registry System: Carbamic acid, methylphenyl-, methyl ester(28685-60-1)

Safety Data

• Hazardous Substances Data: 28685-60-1(Hazardous Substances Data)

Upstream product

• 87463-11-4 O-methyl N-methyl-N-phenylcarbamothioate 
• 67-56-1 methanol 
• 2621-79-6 ethyl N-methyl-N-phenylcarbamate 
• 19009-45-1 N-methyl-N-phenylthiocarbamoyl chloride 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 100-61-8 N-methylaniline 
• 616-38-6 carbonic acid dimethyl ester 
• 100244-44-8 (ethoxydichloromethyl)(methylphenylcarbamoyl)disulfane 
• 100244-43-7 (methoxydichloromethyl)(methylphenylcarbamoyl)disulfane 
• 100244-48-2 ((N-methyl-N-phenylcarbamoyl)dithio)carbonyl chloride 
• 100244-53-9 (N-methyl-N-phenylcarbamoyl)sulfenyl chloride 
• 51480-12-7 Bis(N-methyl-N-phenylcarbamoyl)disulfane 
• 87463-00-1 O-ethyl N-methyl-N-phenylthiocarbamate 
• 36602-08-1 (N-methylanilino)acetonitrile 

Downstream Products

• 10252-27-4 p-Nitrophenyl-N-methyl-carbamidsaeure-methylester 
• 121-69-7 N,N-dimethyl-aniline 
• 67-56-1 methanol 
• 100-61-8 N-methylaniline 
• 5882-44-0 N,N-dimethylaniline hydrochloride 
• 93-61-8 N-methyl-N-phenylformamide 
• 95569-16-7 methyl N-(2,4,6-trinitrophenyl)carbamate 
• 88889-00-3 N-methyl-N-(methyl-d₃)aniline 

Relevant articles and documents

Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates

A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.

Formation of defect site on ZIF-7 and its effect on the methoxycarbonylation of aniline with dimethyl carbonate

The Zeolitic Imidazole Framework ZIF-7, (Zn(benzimidazole)2), is known to exhibit a unique gate-opening property depending on the temperature and pressure in the presence of guest molecules, making it useful for H2, CO2, and paraffine separation technology. Besides this distinctive gas adsorption property, ZIF-7 can be used as a catalyst because it contains a Lewis acid site on Zn, and a Lewis basic site on the benzimidazole. In this study, for the first time, we demonstrate that ZIF-7 is a very promising material as a catalyst for the methoxycarbonylation of aniline with dimethyl carbonate (DMC) to produce methyl phenyl carbamate (MPC), an isocyanate precursor. Fresh ZIF-7 showed a high aniline conversion of over 95% at 190 °C for 2 h, and the yield MPC was 60–70% due to the formation of methylated side products, such as N-methyl aniline and N,N′-dimethylaniline. However, interestingly, when the ZIF-7 was reused, the yield of MPC gradually increased and reached over 94.7% by the catalyst's 6th run. SEM and TEM images revealed the crystalline structure of ZIF-7 collapsed during the reaction due to the leaching of benzimidazole from the ZIF-7, which created defect sites on the Lewis acidic zinc center. Based on 1H NMR and XPS studies, it can be assumed that the DMC binds to the Zn defect sites on the ZIF-7, activating the carbonyl groups on DMC, resulting in the increased selectivity to methoxycarbonylation compared to methylation. Pretreating ZIF-7 with DMC at 190 °C for 6 h could directly activated the ZIF-7 for this methoxycarbonylation reaction. The activated ZIF-7 showed 91.0% MPC yield and the catalyst was reusable.

Aniline carbamates: A versatile and removable motif for palladium-catalyzed directed c-h activation

The aniline carbamate is introduced as a new removable directing group for C-H activation. Its versatility and ability as a directing group are demonstrated by its use in the ortho-arylation of a wide variety of aniline derivatives under palladium(II) catalysis, with symmetric diaryliodonium salts as aryl donors. The reaction differs from previously reported arylations in its selectivity and its mechanism, as elucidated by kinetic and isotopic experiments. The directing group can also be easily removed under a variety of conditions.