Ethyl N-phenylcarbamate

Base Information

• Chemical Name: Ethyl N-phenylcarbamate
• CAS No.: 101-99-5
• Molecular Formula: C9H11 N O2
• Molecular Weight: 165.192
• Hs Code.: 29242990
• European Community (EC) Number: 202-995-9
• NSC Number: 3245
• UNII: TWP7W286IF
• DSSTox Substance ID: DTXSID0059243
• Nikkaji Number: J4.998K
• Wikidata: Q3742461
• ChEMBL ID: CHEMBL2235373
• Mol file: 101-99-5.mol

Synonyms:ethyl N-phenylcarbamate;ethylcarbanilate;phenylurethane

Chemical Property of Ethyl N-phenylcarbamate

Chemical Property:

• Appearance/Colour: colorless to almost white needles
• Vapor Pressure: 0.0434mmHg at 25°C
• Melting Point: 47-51 °C
• Refractive Index: 1.5375
• Boiling Point: 237 °C
• PKA: 13.86±0.70(Predicted)
• Flash Point: 79.2°C
• PSA: 38.33000
• Density: 1.136g/cm³
• LogP: 2.32800
• Storage Temp.: 2-8°C
• Water Solubility.: Practically insoluble in water
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

99% ^*data from raw suppliers

Phenylurethane >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: CCOC(=O)NC1=CC=CC=C1

Technology Process of Ethyl N-phenylcarbamate

There total 203 articles about Ethyl N-phenylcarbamate 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: 94.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + aniline (62-53-3) → quinoline (91-22-5) + 2-methylquinoline (91-63-4) + N-carboethoxyaniline (101-99-5)

Guidance literature:

With oxygen; Sulfate; zirconium(IV) oxide; palladium dichloride; at 170 ℃; for 1h; under 45003.6 Torr; Title compound not separated from byproducts;

DOI:10.1006/jcat.2001.3350

Reference yield: 78.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + nitrobenzene (98-95-3,26969-40-4) → N-carboethoxyaniline (101-99-5) + aniline (62-53-3)

Guidance literature:

With bis(triphenylphosphine)platinum(II) dichloride; tin(IV) chloride; triethylamine; at 180 ℃; for 4h; under 45600 Torr;

DOI:10.1246/cl.1982.105

Reference yield: 53.0%

triethyl borane (97-94-9) + phenyl isocyanate (103-71-9) + N,N-diethylaniline (91-66-7) → 2-(ethylphenylamino)-N-phenylpropanamide + 1-(2-(ethylphenylamino)propanoyl)-1,3-diphenylurea + N-carboethoxyaniline (101-99-5) + 1-ethyl-1,3-diphenyl urea (64544-71-4)

Guidance literature:

With air; at 20 ℃; for 23h; Further byproducts.;

DOI:10.1021/ol7023295

upstream raw materials:

1,2,4,4-tetrachlorohexafluorobutane

2,4-diphenyl-allophanic acid ethyl ester

ethanol

phenylcarbonimidic dichloride

Downstream raw materials:

ethoxycarbonyl-phenyl-oxalamic acid

N,N-diphenylurea

Phenetole

bis(diphenyl)urea

Refernces

• 1、 Lu, Yuhua,Taylor, Richard T.. "Preparation and applications of a polymer-supported phosphoryl azide". . p. 9267 - 9269. Retrieved 2003.
• 2、 Lapidus, A. L.,Lunin, A. F.,Pirozhkov, S. D.,Leonchik, N. B.,Neittsel', P.,Shvetlik, K.. "SYNTHESIS OF PHENYLURETHANES BY CARBONYLATION OF NITROBENZENE IN THE PRESENCE OF PALLADIUM CATALYSTS". . p. 1068 - 1070. Retrieved 1981.
• 3、 Manov-Yuvenskii, V. I.,Nefedov, B. K.,Khoshdurdyev, Kh. O.. "SOME FEATURES OF THE SYNTHESIS OF URETHANES BY THE CARBONYLATION OF NITROBENZENES IN ALCOHOLIC SOLUTION". . p. 1176 - 1178. Retrieved 1982.
• 4、 Watanabe, Yoshihisa,Tsuji, Yasushi,Suzuki, Naoki. "THE PLATINUM COMPLEX CATALYZED REDUCTIVE CARBONYLATION OF NITROARENE TO URETHANE". . p. 105 - 106. Retrieved 1982.
• 5、 Sagandira, Cloudius R.,Watts, Paul. "Synthesis of Amines, Carbamates and Amides by Multi-Step Continuous Flow Synthesis". . p. 6554 - 6565. Retrieved 2017.
• 6、 Casadei, Maria A.,Inesi, Achille,Moracci, Franco Micheletti,Rossi, Leucio. "Electrochemical activation of carbon dioxide: Synthesis of carbamates". . p. 2575 - 2576. Retrieved 1996.
• 7、 Barani, Marco,Fioravanti, Stefania,Antonietta Loreto,Pellacani, Lucio,Tardella, Paolo A.. "Improved amination by ethyl n-(4-nitrophenyl)sulphonyloxy carbamate in the presence of inorganic oxides or carbonates". . p. 3829 - 3834. Retrieved 1994.
• 8、 Entenmann. "-". . p. 377. Retrieved 1975.
• 9、 Haenig, K.,Grosse-Ruyken, H.,Ruehlmann, K.,Schlapa, J.. "UEBER DIE Si-N-BINDUNG. XLIII. KINETISCHE UNTERSUCHUNGEN ZUR HYDROLYSE VON SILYLURETHANEN DES TYPS (p-XC6H4)Me2SiN(Ph)COOEt". . p. 145 - 158. Retrieved 1984.
• 10、 Zhang, Qiao,Yuan, Hao-Yu,Fukaya, Norihisa,Yasuda, Hiroyuki,Choi, Jun-Chul. "Direct synthesis of carbamate from CO2 using a task-specific ionic liquid catalyst". . p. 5614 - 5624. Retrieved 2017.