622-46-8

Basic information

• Product Name: Phenyl carbamate
• Synonyms: PHENYL CARBAMATE;Phenylcarbamate,98+%;CARBAMICACID,PHENYLESTER;o-Phenyl carbamate;Phenyl carbamate,97%;Phenyl carbaMate 97%
• CAS NO: 622-46-8
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14
• EINECS: 210-737-1
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Protected Amines
• Mol File: 622-46-8.mol

Chemical Properties

• Melting Point: 149-152 °C(lit.)
• Boiling Point: 251.96°C (rough estimate)
• Flash Point: 159.3 °C
• Appearance: white to very slightly pink crystalline flakes
• Density: 1.2528 (rough estimate)
• Vapor Pressure: 0.00416mmHg at 25°C
• Refractive Index: 1.5030 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.33±0.50(Predicted)
• Water Solubility: Soluble in water.
• BRN: 2042627
• CAS DataBase Reference: Phenyl carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl carbamate(622-46-8)
• EPA Substance Registry System: Phenyl carbamate(622-46-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 622-46-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Phenyl carbamate is used as a prodrug for protecting phenolic drugs against first-pass metabolism following oral administration. It is utilized in the preparation of various phenyl carbamate esters derived from amino acids, dipeptides, and amino acid esters and amides, which serve as potential prodrugs.
2. Used in Chemical Synthesis:
Phenyl carbamate is used as a robust, inert reagent in Pd-catalyzed reactions, which are useful for arene functionalization and site-selective cross-coupling reactions. This application takes advantage of its mild reaction conditions and broad functional-group tolerance, allowing for efficient and selective synthesis of target compounds.
3. Used in Organic Chemistry:
Phenyl carbamate is employed in the tin-catalyzed transcarbamoylation of primary and secondary alcohols, generating the corresponding carbamates in good yields. This method is particularly useful for the synthesis of various organic compounds, as it proceeds smoothly in toluene at 90℃.

InChI:InChI=1/C7H7NO2/c8-7(9)10-6-4-2-1-3-5-6/h1-5H,(H2,8,9)

Upstream product

• 64-17-5 ethanol 
• 24721-92-4 1-Dimethylamino-ethanol 
• 103-71-9 phenyl isocyanate 
• 420-33-7 carbamic acid fluoride 
• 108-95-2 phenol 
• 1885-14-9 phenyl chloroformate 
• 60-29-7 diethyl ether 
• 17759-97-6 carbamic acid bromide 
• 463-72-9 carbamic chloride 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 7664-41-7 ammonia 
• 144-55-8 sodium hydrogencarbonate 
• 101258-79-1 1,2,2-Trimethylpiperidin 

Downstream Products

• 954-67-6 benzhydryl acetate 
• 34197-71-2 Phenyl N-(benzhydryl)carbamate 
• 638-42-6 pentyl carbamate 
• 41177-26-8 N-(cyclohex-2-enyl) phenyl carbamate 
• 1065638-85-8 2-{{[(2Z)-3-butyl-5-tert-butyl-1,3-thiazol-2(3H)-ylidene]amino}[(phenoxycarbonyl)imino]methyl}-4-chlorophenyl acetate 
• 1010408-55-5 C₁₇H₂₂FN₅O₄ 
• 1017034-89-7 3-ureidophenyl acetylene 
• 103-50-4 dibenzyl ether 
• 65141-19-7 (3,5-bis-trifluoromethylphenyl)carbamic acid phenyl ester 
• 1152171-49-7 1-{(2S,3R)-2-[(S)-3-(4-Fluoro-benzyl)-piperidine-1-carbonyl]-tetrahydro-pyran-3-yl}-3-[3-(1-methyl-1H-tetrazol-5-yl)-phenyl]-urea 
• 30094-69-0 (2,2,2-Trimethoxy-5-phenyl-2λ⁵-[1,3,2]dioxaphosphole-4-carbonyl)-carbamic acid phenyl ester 
• 30094-68-9 (2,2,2-Trimethoxy-5-methyl-2λ⁵-[1,3,2]dioxaphosphole-4-carbonyl)-carbamic acid phenyl ester 
• 33236-30-5 5-methyl-1-oxo-3,6-dihydro-1H-1λ⁴-[1,2]thiazine-2-carboxylic acid phenyl ester 
• 33236-29-2 1-oxo-3,6-dihydro-1H-1λ⁴-[1,2]thiazine-2-carboxylic acid phenyl ester 

Relevant articles and documents

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Triazinetriamine-derived porous organic polymer-supported copper nanoparticles (Cu-NPs@TzTa-POP): an efficient catalyst for the synthesis of: N -methylated products via CO2fixation and primary carbamates from alcohols and urea

In recent times, carbon dioxide fixation has received much attention for its potential application as an abundant C1 source and a range of important fine chemicals can be manufactured via this fixation. Here, a copper nanoparticle-decorated porous organic polymer-based (Cu-NPs@TzTa-POP) material was prepared by a simple in situ process. The catalyst was characterized by various techniques such as UV-vis spectra, FTIR spectra, HR-TEM, PXRD, N2 adsorption-desorption, TG-DTA, XPS, and AAS analysis. The synthesized heterogeneous catalyst showed excellent activity in an atmospheric carbon dioxide fixation reaction to produce N-methylated products from aromatic/heterocyclic amines in the presence of polymethyl-hydrosiloxane (PMHS) as the reducing agent at 80 °C within 12 h of the reaction. Through this catalytic N-methylation reaction, we obtained 98% yield of the product with turnover frequency ranging from 18 to 42 h-1. The catalyst is also very stable for the formation of primary carbamates from alcohols using the eco-friendly carbonylating agent, urea. Diverse alcohols (such as benzylic alcohols, phenols, heterocyclic alcohols, as well as aliphatic alcohols) showed much acceptance to this catalytic reaction and produced moderate to excellent yields of the respective carbamate products under ambient reaction conditions. Moreover, Cu-NPs@TzTa-POP is effortlessly recyclable and reusable without the extensive loss of active copper metal centres for many catalytic rounds (up to six catalytic rounds were examined).

TETRAHYDROPYRAN (THP)-SUBSTITUTED BICYCLIC-PYRIMIDINEDIONE COMPOUNDS

The present disclosure provides novel tetrahydropyran (THP)-substituted bicyclic pyrimidinedione compounds that are useful for the treatment of hypertrophic cardiomyopathy (HCM), conditions associated with left ventricular hypertrophy, conditions associated with diastolic dysfunction, and/or symptoms associated thereof. The synthesis and characterization of the compounds is described, as well as methods for treating HCM and other forms of heart disease.

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas

Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.

Reaction method accompanied by production of gas component

The present invention relates to a reaction method comprising a step of supplying a liquid containing at least one raw material compound and a low-boiling compound having a standard boiling point lower than a standard boiling point of the raw material compound to a flow channel, a step of heating the liquid to produce a liquid reaction product and a gas component by a reaction of the raw material compound, and a step of separating a liquid phase containing the reaction product from a gas phase containing the gas component and the low-boiling compound.

SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS

The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas

A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.

FLUORESCENT MARKERS AND USE THEREOF FOR LABELING SPECIFIC PROTEIN TARGETS

Novel fluorescent markers of Formula I: are disclosed herein, wherein X and Y are independently or together absent or are independently selected from R and R1 are independently selected from H and alkyl; Ar is phenyl or heteroaryl; L is absent or a spacer selected from the group consisting of —NH—; —(CH2)nNH—; —NHSO2—; —(CH2)nNHCO—; -(cycloalkyl)NHCO—; —(CH2)nNHSO2—; -(cycloalkyl)NHSO2—; —CONH(CH2)nNHCO—; —CONH(cycloalkyl)NHCO—; —NHCO(CH2)nNHCO—; —NHCO(cycloalkyl)NHCO—; —(CH2)nSO2NH—; -(cycloalkyl)SO2NH—; —(CH2)nNHCSNH—; -(cycloalkyl)NHCSNH—; —CR═CR1—; —C≡C—; —(CH2)nN═CH—; -(cycloalkyl)N═CH—; —N═CH(CH2)—; —N═CH(cycloalkyl)-; n is an integer ranging from 1 to 5; F is a fluorophore selected from the group consisting of fluorescein, rhodamine, eosin, thionine, safranin, coumarin, methoxycoumarin, dansyl, BODIPY and BODIPY derivatives; and wherein X, Y and L may be positioned in a 1,3,5; 1,2,3; 1,3,4 or in a 3,4,5 configuration respectively.

Anilinolysis of reactive aryl 2,4-dinitrophenyl carbonates: Kinetics and mechanism

The reactions of a series of anilines with phenyl 2,4-dinitrophenyl (1), 4-nitrophenyl 2,4-dinitrophenyl (2), and bis(2,4-dinitrophenyl) (3) carbonates are subjected to a kinetic investigation in 44 wt% ethanol-water, at 25.0 ± 0.1°C and an ionic strength of 0.2 M. Under amine excess pseudo-first-order rate coefficients (kobs) are obtained. Plots of kobs against free amine concentration at constant pH are linear, with slopes kN. The BrAnsted plots (log kN vs. anilinium pKa) for the anilinolysis of 1-3 are linear, with slope (β) values of 0.52, 0.61, and 0.63, respectively. The values of these slopes and other considerations suggest that these reactions are ruled by a concerted mechanism. For these reactions, the kN values follow the reactivity sequence: 3 > 2 > 1. Namely, the reactivity increases as the number of nitro groups attached to the nonleaving group increases. Comparison of the reactions of this work with the stepwise pyridinolysis of carbonates 1-3 indicates that the zwitterionic tetrahedral intermediate (T±) formed in the pyridinolysis reactions is destabilized by the change of its pyridino moiety by an isobasic anilino group. This is attributed to the superior leaving ability from the T± intermediate of anilines, relative to isobasic pyridines, which destabilize kinetically this intermediate. The kN values for the anilinolysis of carbonates 1-3 are similar to those found in the reactions of these carbonates with secondary alicyclic amines. With the kinetic data for the anilinolysis of the title substrates and 4-methylphenyl and 4-chlorophenyl 2,4-dinitrophenyl carbonates, a multiparametric equation is derived for log kN as a function of the pKa of the conjugate acids of anilines and nonleaving groups.

An efficient synthesis of carbamates by tin-catalyzed transcarbamoylation reactions of primary and secondary alcohols

A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 ° C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance. Georg Thieme Verlag Stuttgart.