Phenyl carbamate

Base Information

• Chemical Name: Phenyl carbamate
• CAS No.: 622-46-8
• Molecular Formula: C7H7NO2
• Molecular Weight: 137.138
• Hs Code.: 29242998
• European Community (EC) Number: 210-737-1
• NSC Number: 66509
• UNII: JKB257U27V
• DSSTox Substance ID: DTXSID20211237
• Nikkaji Number: J126.337D
• Wikidata: Q27281550
• ChEMBL ID: CHEMBL173183
• Mol file: 622-46-8.mol

Synonyms:Phenyl carbamate;622-46-8;Carbamic acid, phenyl ester;Carbamic acid phenyl ester;phenol carbamate;CCRIS 5071;EINECS 210-737-1;NSC 66509;UNII-JKB257U27V;AI3-50866;JKB257U27V;MFCD00007961;NSC-66509;O-Phenyl carbamate;mono-phenylcarbamate;mono-phenol carbamate;Phenyl carbamate, 97%;SCHEMBL7566;CHEMBL173183;SCHEMBL11857065;DTXSID20211237;CHEBI:195069;NSC66509;Carbamic acid, phenyl ester (8CI);STK368404;AKOS005444173;CS-16342;NCI60_022430;SY109407;LS-188181;CS-0095625;FT-0632612;EN300-94219;A833672;Q27281550;Z33547080

Chemical Property of Phenyl carbamate

Chemical Property:

• Appearance/Colour: white to very slightly pink crystalline flakes
• Vapor Pressure: 0.00416mmHg at 25°C
• Melting Point: 149-152 °C(lit.)
• Refractive Index: 1.551
• Boiling Point: 278.9 °C at 760 mmHg
• PKA: 12.33±0.50(Predicted)
• Flash Point: 159.3 °C
• PSA: 52.32000
• Density: 1.2 g/cm³
• LogP: 1.84440
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 137.047678466
• Heavy Atom Count: 10
• Complexity: 119

Purity/Quality:

98%,99%, ^*data from raw suppliers

Phenyl carbamate 97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC(=O)N
• Uses: Phenyl carbamate is used as various phenyl carbamate esters derived from amino acids, a dipeptide and amino acid esters and amides were prepared and assessed as potential prodrugs with the aim of protecting phenolic drugs against first-pass metabolism following per oral administration. A tin-catalyzed transcarbamoylation of primary and secondary alcohols with phenyl carbamate proceeds smoothly in toluene at 90℃ to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance. Y. Ichikawa, Y. Morishita, S. Kusaba, N. Sakiyama, Y. Matsuda, K. Nakano, H. Kotsuki, Synlett, 2010, 1815-1818. http://dx.doi.org/10.1055/s-0030-1258102 Phenyl Carbamate is a robust, inert to Pd-catalysis reagent which are useful for arene functionalization/site-selective cross-coupling reactions.

Technology Process of Phenyl carbamate

There total 39 articles about Phenyl carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

DMAE phenylcarbamate + diethyl ether (60-29-7,927820-24-4) + methyl iodide (74-88-4) → carbamic acid phenyl ester (622-46-8)

Guidance literature:

In acetone;

Reference yield: 84.0%

phenyl chloroformate (1885-14-9) → carbamic acid phenyl ester (622-46-8)

Guidance literature:

With ammonia; In dichloromethane; water; at 0 ℃;

DOI:10.1055/s-0030-1258102

Reference yield: 83.0%

(1R,2R)-7-[4-(4-Aminophenyl)-1-piperazinyl]-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]quinazolin-4(3H)-one + sodium hydrogencarbonate (144-55-8) + phenyl chloroformate (1885-14-9) → carbamic acid phenyl ester (622-46-8)

Guidance literature:

In pyridine;

upstream raw materials:

phenyl chloroformate

diethyl ether

carbamic chloride

phenol

Downstream raw materials:

cyanic acid

phenol

N,N'-Methylen-bis-

phenyl isocyanatoformate

Refernces

• 1、 Lapidus, A. L.,Pirozhkov, S. D.,Antipov, Yu. V.. "SYNTHESIS OF CARBAMATES BY CARBONYLATION OF NITRO COMPOUNDS IN THE PRESENCE OF THIOUREA". . p. 2177. Retrieved 1983.
• 2、 -. "TETRAHYDROPYRAN (THP)-SUBSTITUTED BICYCLIC-PYRIMIDINEDIONE COMPOUNDS". Paragraph 0153. . Retrieved 2020/05/28.
• 3、 Inaloo, Iman Dindarloo,Majnooni, Sahar,Esmaeilpour, Mohsen. "Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas". . p. 3481 - 3488. Retrieved 2018/07/29.