Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI)
• CAS No.: 108714-89-2
• Molecular Formula: C15H15NO2
• Molecular Weight: 241.29
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90358441
• Nikkaji Number: J3.163.755D
• Wikidata: Q82139003
• ChEMBL ID: CHEMBL1463374
• Mol file: 108714-89-2.mol

Synonyms:Benzyl o-tolylcarbamate;108714-89-2;benzyl N-(2-methylphenyl)carbamate;Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI);Benzylo-tolylcarbamate;benzyl 2-methylphenylcarbamate;MLS001000903;SCHEMBL5853278;CHEMBL1463374;benzyl (2-methylphenyl)carbamate;DTXSID90358441;HMS2817D10;AKOS003351344;SMR000497757;CS-0329689;AG-205/04687058;SR-01000267784;SR-01000267784-1

Chemical Property of Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI)

Chemical Property:

• PSA: 41.82000
• LogP: 3.75730
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 241.110278721
• Heavy Atom Count: 18
• Complexity: 261

Purity/Quality:

Benzylo-tolylcarbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC(=O)OCC2=CC=CC=C2

Technology Process of Carbamic acid, (2-methylphenyl)-, phenylmethyl ester (9CI)

There total 10 articles about Carbamic acid, (2-methylphenyl)-, 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: 99.0%

ortho-toluoyl chloride (933-88-0) + benzyl alcohol (100-51-6,185532-71-2) → N-benzyloxycarbonyl-2-methylaniline (108714-89-2)

Guidance literature:

ortho-toluoyl chloride; With pyridine; trimethylsilylazide; In N,N-dimethyl-formamide; at 20 ℃; Microflow reaction; Inert atmosphere;

benzyl alcohol; With acetic acid; In N,N-dimethyl-formamide; at 110 ℃; Microflow reaction; Inert atmosphere;

DOI:10.1002/ejoc.201100074

Reference yield: 84.0%

carbon dioxide (124-38-9,18923-20-1) + 2-methyl-N-(triphenylphosphanylidene)anilinium bromide + benzyl alcohol (100-51-6,185532-71-2) → N-benzyloxycarbonyl-2-methylaniline (108714-89-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 85 ℃;

DOI:10.1039/d1cc01016f

Reference yield: 72.0%

C16H15NO4 → N-benzyloxycarbonyl-2-methylaniline (108714-89-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In chlorobenzene; at 120 ℃; for 2.5h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b02724

upstream raw materials:

2-tolyl isocyanate

benzyl alcohol

o-toluene-diazonium chloride

ortho-toluoyl chloride

Downstream raw materials:

iodomethylbenzene

benzyl ((2-methyloxiran-2-yl)methyl)(o-tolyl)carbamate

methyl o-tolyl carbamic acid 1-benzyl ester

2-tolyl isocyanate

Refernces

• 1、 Sardarian, Ali Reza,DindarlooInaloo, Iman,Zangiabadi, Milad. "Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids". . p. 642 - 652. Retrieved 2018/01/11.
• 2、 Dai, Qipu,Li, Peihe,Ma, Nuannuan,Hu, Changwen. "Palladium-Catalyzed Decarboxylative Synthesis of Arylamines". supporting information. p. 5560 - 5563. Retrieved 2016/11/17.