16744-99-3

Basic information

• Product Name: Carbamic acid, (4-fluorophenyl)-, methyl ester
• Synonyms: (4-Fluoro-phenyl)-carbamic acid methyl ester;N-<4-Fluor-phenyl>-methylurethan;N-(4-Fluor-phenyl)-methylurethan;methyl (4-fluorophenyl)carbamate;Methyl-N-p-fluorphenyl-carbamat;ethyl 4-fluorophenylcarbamate;methyl (4-fluorophenyl)-carbamate
• CAS NO: 16744-99-3
• Molecular Formula: C8H8FNO2
• Molecular Weight: 169.155
• Mol File: 16744-99-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 92 - 94 °C
• Boiling Point: 185.5±23.0 °C(Predicted)
• Density: 1.270±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Carbamic acid, (4-fluorophenyl)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (4-fluorophenyl)-, methyl ester(16744-99-3)
• EPA Substance Registry System: Carbamic acid, (4-fluorophenyl)-, methyl ester(16744-99-3)

Safety Data

• Hazardous Substances Data: 16744-99-3(Hazardous Substances Data)

Upstream product

• 681-84-5 tetramethylorthosilicate 
• 124-38-9 carbon dioxide 
• 371-40-4 4-fluoroaniline 
• 74-88-4 methyl iodide 
• 6294-89-9 hydrazinecarboxylic acid methyl ester 
• 67-56-1 methanol 
• 824-75-9 p-fluorobenzamide 
• 201230-82-2 carbon monoxide 
• 1195-45-5 para-fluorophenyl isocyanate 
• 590-28-3 potassium cyanate 
• 1765-93-1 4-fluoroboronic acid 
• 79-22-1 methyl chloroformate 

Downstream Products

• 50844-60-5 3-(4-fluorophenyl)-6-(trifluoromethyl)pyrimidine-2,4-(1H,3H)-dione 
• 146423-48-5 3-(4-fluorophenyl)-1-methyl-6-(trifluorometheyl)pyrimidine-2,4(1H,3H)-dione 
• 1357510-75-8 2-(5-fluoro-2,4-dinitrophenoxy)-N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)propanamide 
• 1048953-53-2 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)-2-(4-nitrophenoxy)acetamide 
• 1048953-57-6 2-(biphenyl-4-yloxy)-N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)propanamide 
• 1048953-56-5 2-(2-fluoro-4-nitrophenoxy)-N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)propanamide 
• 1048953-78-1 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-(4-(methylthio)phenoxy)propanamide 
• 1357510-59-8 2-(2,4-dichlorophenoxy)-N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)acetamide 
• 1048953-72-5 2-(4-chloro-3-methylphenoxy)-N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)propanamide 
• 1048953-70-3 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-phenoxypropanamide 
• 1048953-50-9 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-(3-fluorophenoxy)propanamide 
• 1048953-52-1 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-(para-tolyloxy)propanamide 
• 1048953-51-0 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-(m-tolyloxy)propanamide 
• 1048953-54-3 N-(2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydro-pyrimidin-1(6H)-yl)phenyl)-2-(2-methoxyphenoxy)propanamide 

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.

N-Aryl and N-Alkyl Carbamates from 1 Atmosphere of CO2

We have successfully isolated and characterized the zinc carbamate complex (phen)Zn(OAc)(OC(=O)NHPh) (1; phen=1,10-phenanthroline), formed as an intermediate during the Zn(OAc)2/phen-catalyzed synthesis of organic carbamates from CO2, amines, and the reusable reactant Si(OMe)4. Density functional theory calculations revealed that the direct reaction of 1 with Si(OMe)4 proceeds via a five-coordinate silicon intermediate, forming organic carbamates. Based on these results, the catalytic system was improved by using Si(OMe)4 as the reaction solvent and additives like KOMe and KF, which promote the formation of the five-coordinated silicon species. This sustainable and effective method can be used to synthesize various N-aryl and N-alkyl carbamates, including industrially important polyurethane raw materials, starting from CO2 under atmospheric pressure.

Calcium carbide as a dehydrating agent for the synthesis of carbamates, glycerol carbonate, and cyclic carbonates from carbon dioxide

Carbon dioxide (CO2) is a nontoxic and inexpensive C1 building block, which can be used for the synthesis of valuable chemicals such as aromatic carbamates from anilines and methanol (MeOH), glycerol carbonate from glycerol, and cyclic carbonates from diols. However, these reactions generate water as the byproduct and suffer from thermodynamic limits, which lead to low yields. Calcium carbide (CaC2) is a renewable chemical, which can be recycled from calcium that is abundant in the Earth's crust. Furthermore, CaC2 rapidly reacts with water. In this work, we used CaC2 as a dehydrating agent for the direct synthesis of carbamates (including polyurethane precursors) from amines, CO2, and MeOH. All reagents were commercially available. In addition, CaC2 was employed for the synthesis of glycerol carbonate from glycerol and CO2 with a zinc catalyst and N-donor ligand. A similar protocol was applied to synthesize cyclic carbonates from diols and CO2.