Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Base Information

• Chemical Name: Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate
• CAS No.: 796848-80-1
• Molecular Formula: C13H10ClNO3
• Molecular Weight: 263.68
• DSSTox Substance ID: DTXSID10460979
• Wikidata: Q82285183
• Mol file: 796848-80-1.mol

Synonyms:796848-80-1;Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate;phenyl (2-chloro-4-hydroxyphenyl)carbamate;phenyl 2-chloro-4-hydroxyphenylcarbaMate;Carbamic acid, (2-chloro-4-hydroxyphenyl)-, phenyl ester;SCHEMBL1322757;DTXSID10460979;LBDLNHLYEKFAHH-UHFFFAOYSA-N;MFCD21438014;AKOS014117348;AC-33716;phenyl(2-chloro-4-hydroxyphenyl)carbamate;CS-0168591;Phenyl N-?(2-?Chloro-?4-?hydroxyphenyl)?carbamate

Chemical Property of Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

Chemical Property:

• Boiling Point: 392.1±42.0 °C(Predicted)
• PKA: 9.07±0.31(Predicted)
• PSA: 62.05000
• Density: 1.426±0.06 g/cm3(Predicted)
• LogP: 3.67010
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 263.0349209
• Heavy Atom Count: 18
• Complexity: 281

Purity/Quality:

98% ^*data from raw suppliers

PhenylN-?(2-?Chloro-?4-?hydroxyphenyl)?carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC(=O)NC2=C(C=C(C=C2)O)Cl
• Uses: Phenyl N-?(2-?Chloro-?4-?hydroxyphenyl)?carbamate is a reagent used in the prepartion of quinoline-carboxamide compounds including Lenvatinib (L329400), an orally active inhibitor of multiple receptor tyrosine kinases including VEGF, FGF and SCF receptors.

Technology Process of Phenyl N-(2-chloro-4-hydroxyphenyl)carbamate

There total 3 articles about Phenyl N-(2-chloro-4-hydroxyphenyl)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%

4-amino-3-chlorophenol (17609-80-2) + phenyl chloroformate (1885-14-9) → phenyl N-(2-chloro-4-hydroxyphenyl)carbamate (796848-80-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 24h; Cooling with ice;

DOI:10.1016/j.ejmech.2019.111614

Reference yield:

4-amino-3-chloro-phenol hydrochloride + phenyl chloroformate (1885-14-9) → phenyl N-(2-chloro-4-hydroxyphenyl)carbamate (796848-80-1)

Guidance literature:

4-amino-3-chloro-phenol hydrochloride; With sodium hydrogencarbonate; In 2-methyltetrahydrofuran; water; at 0 - 10 ℃; for 0.416667h;

phenyl chloroformate; In 2-methyltetrahydrofuran; water; at 0 - 10 ℃; for 0.583333h;

Reference yield:

6N-HCl + 4-amino-3-chlorophenol (17609-80-2) + phenyl chloroformate (1885-14-9) → phenyl N-(2-chloro-4-hydroxyphenyl)carbamate (796848-80-1)

Guidance literature:

With pyridine; In water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

4-amino-3-chlorophenol

phenyl chloroformate

Downstream raw materials:

lenvatinib

1-(2-chloro-4-hydroxyphenyl)-3-cyclopropyl urea

Refernces

• 1、 -. "Isotope enrichment lenvatinib". Paragraph 0070; 0089; 0094; 0096; 0100; 0105. . Retrieved 2020/03/09.
• 2、 Moi, Davide,Foster, Paul A.,Rimmer, Lucy G.,Jaffri, Alisha,Deplano, Alessandro,Balboni, Gianfranco,Onnis, Valentina,Potter, Barry V.L.. "Synthesis and in vitro evaluation of piperazinyl-ureido sulfamates as steroid sulfatase inhibitors". . . Retrieved 2019/08/20.