Tert-butyl o-tolylcarbamate

Base Information

• Chemical Name: Tert-butyl o-tolylcarbamate
• CAS No.: 74965-31-4
• Molecular Formula: C12H17 N O2
• Molecular Weight: 207.272
• Hs Code.: 2924299090
• European Community (EC) Number: 800-205-2
• DSSTox Substance ID: DTXSID20431175
• Nikkaji Number: J416.448B
• Wikidata: Q82244993
• Mol file: 74965-31-4.mol

Synonyms:tert-butyl o-tolylcarbamate;74965-31-4;o-Tolyl-carbamic acid tert-butyl ester;Tert-butyl N-(2-methylphenyl)carbamate;N-(tert-Butoxycarbonyl)-2-methylaniline;tert-butyl?o-tolylcarbamate;SCHEMBL1534089;DTXSID20431175;AMY15414;FD7306;MFCD09031443;AKOS014476257;SB77108;SS-4564;tert-Butyl-N-(2-methylphenyl)carbamate;AC-20606;CS-0315615;FT-0663999;A849981;N-(2-Methylphenyl)-carbamic acid tert-butyl ester;J-524809

Chemical Property of Tert-butyl o-tolylcarbamate

Chemical Property:

• Vapor Pressure: 0.022mmHg at 25°C
• Melting Point: 82-83 °C
• Refractive Index: 1.539
• Boiling Point: 250.447°C at 760 mmHg
• PKA: 13.87±0.70(Predicted)
• Flash Point: 105.267°C
• PSA: 38.33000
• Density: 1.064g/cm³
• LogP: 3.41500
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 220

Purity/Quality:

98%min ^*data from raw suppliers

N-(tert-Butoxycarbonyl)-2-methylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC(=O)OC(C)(C)C

Technology Process of Tert-butyl o-tolylcarbamate

There total 12 articles about Tert-butyl o-tolylcarbamate 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%

di-tert-butyl dicarbonate (24424-99-5) + o-toluidine (95-53-4) → N-(tert-butoxycarbonyl)-o-toluidine (74965-31-4)

Guidance literature:

copper(II) bis(tetrafluoroborate); at 30 - 33 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.12.044

Reference yield: 94.0%

tert-butyl carbazate (4248-19-5) + 2-methylphenyl bromide (95-46-5) → N-(tert-butoxycarbonyl)-o-toluidine (74965-31-4)

Guidance literature:

With ?di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); triisopropylsilanol; potassium hydroxide; In water; at 50 ℃; for 24h; Inert atmosphere; Green chemistry;

DOI:10.1039/c3gc42188k

Reference yield: 86.0%

t-butyl [(2-methylbenzoyl)oxy]carbamate → N-(tert-butoxycarbonyl)-o-toluidine (74965-31-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate; In chlorobenzene; at 85 ℃; for 1h; Reagent/catalyst; Solvent; regioselective reaction; Catalytic behavior; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b02724

upstream raw materials:

di-tert-butyl dicarbonate

o-toluidine

tert-butyl phenylcarbamate

methyl iodide

Downstream raw materials:

[2-(2-Oxo-propyl)-phenyl]-carbamic acid tert-butyl ester

2-tert-butylthiomethyl-N-tert-butoxycarbonylaniline

4-(2-aminophenyl)-2-butanol

N-allyl-o-toluidine

Refernces

• 1、 Pise, Ashok S.,Ingale, Ajit P.,Dalvi, Navnath R.. "Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate". supporting information. p. 3768 - 3780. Retrieved 2021/10/26.
• 2、 Ingale, Ajit P.,Garad, Dnyaneshwar N.,Ukale, Dattatraya,Thorat, Nitin M.,Shinde, Sandeep V.. "Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines". supporting information. p. 3791 - 3804. Retrieved 2021/11/04.