Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI)
• CAS No.: 19972-88-4
• Molecular Formula: C14H13NO3
• Molecular Weight: 243.262
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90173772
• Nikkaji Number: J42.847G
• Wikidata: Q83043790
• Mol file: 19972-88-4.mol

Synonyms:19972-88-4;Benzyl m-hydroxycarbanilate;Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI);benzyl N-(3-hydroxyphenyl)carbamate;m-Hydroxycarbanilic acid benzyl ester;Phenylmethyl (3-hydroxyphenyl)carbamate;BRN 4451293;CARBANILIC ACID, m-HYDROXY-, BENZYL ESTER;Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester;SCHEMBL8984657;3-(Benzyloxycarbonylamino)phenol;DTXSID90173772;LS-51308;EN300-7243439

Chemical Property of Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI)

Chemical Property:

• Vapor Pressure: 2.9E-06mmHg at 25°C
• Boiling Point: 378.4°C at 760 mmHg
• PKA: 9.68±0.10(Predicted)
• Flash Point: 182.6°C
• PSA: 62.05000
• Density: 1.293g/cm³
• LogP: 3.15450
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 243.08954328
• Heavy Atom Count: 18
• Complexity: 264

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC2=CC(=CC=C2)O

Technology Process of Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI)

There total 5 articles about Carbamic acid, (3-hydroxyphenyl)-, phenylmethyl ester (9CI) 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: 100.0%

benzyl chloroformate (501-53-1,94274-21-2) + m-Hydroxyaniline (591-27-5) → 3-Hydroxycarbanilic Acid Benzyl Ester (19972-88-4)

Guidance literature:

In diethyl ether; for 18h; Ambient temperature;

DOI:10.1021/jo01300a003

Reference yield: 75.0%

m-tetrahydropyran-2-yloxy-N-(benzyloxycarbonyl)aminobenzene (515163-28-7) → 3-Hydroxycarbanilic Acid Benzyl Ester (19972-88-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1h; Heating;

DOI:10.3987/com-02-s27

Reference yield:

meta-nitrophenol (554-84-7) → 3-Hydroxycarbanilic Acid Benzyl Ester (19972-88-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / TsOH*H₂O / benzene / 1 h / 50 °C

2: hydrogen / 10 percent Pd/C / ethanol / 4 h / 20 °C / 760 Torr

3: 14.39 g / CHCl₃ / 2 h / 20 °C

4: 75 percent / TsOH*H₂O / methanol / 1 h / Heating

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; chloroform; benzene;

DOI:10.3987/com-02-s27

upstream raw materials:

benzyl chloroformate

m-Hydroxyaniline

m-tetrahydropyran-2-yloxy-N-(benzyloxycarbonyl)aminobenzene

meta-nitrophenol

Downstream raw materials:

2-allyl-5-N-(benzyloxycarbonyl)aminophenol

2-allyl-3-N-(benzyloxycarbonyl)aminophenol

allyl 3-N-(benzyloxycarbonyl)aminophenyl ether

Refernces

• 1、 Pan, Le,Lei, Dongyu,Jin, Lu,He, Yuan,Yang, Qingqing. "Promising fungicides from allelochemicals: Synthesis of umbelliferone derivatives and their structure–activity relationships". . . Retrieved 2018/11/24.
• 2、 Sekizaki, Haruo,Itoh, Kunihiko,Toyota, Eiko,Tanizawa, Kazutaka. "A facile synthesis of benzofuran derivatives: A useful synthon for preparation of trypsin inhibitor". . p. 237 - 243. Retrieved 2007/10/03.