Tert-butyl (2-aminophenyl)carbamate

Base Information

• Chemical Name: Tert-butyl (2-aminophenyl)carbamate
• CAS No.: 146651-75-4
• Molecular Formula: C11H16N2O2
• Molecular Weight: 208.26
• Hs Code.: 2924299090
• European Community (EC) Number: 625-192-9
• DSSTox Substance ID: DTXSID60350275
• Nikkaji Number: J853.089K
• Wikidata: Q82126130
• Mol file: 146651-75-4.mol

Synonyms:146651-75-4;Tert-butyl (2-aminophenyl)carbamate;tert-butyl 2-aminophenylcarbamate;N-Boc-1,2-phenylenediamine;tert-butyl N-(2-aminophenyl)carbamate;(2-Amino-phenyl)-carbamic Acid Tert-butyl Ester;(2-amino-phenyl)carbamic acid tert-butyl ester;MFCD02169707;tert-butyl(2-aminophenyl)carbamate;Carbamic acid, (2-aminophenyl)-, 1,1-dimethylethyl ester;(2-aminophenyl)carbamic acid tert-butyl ester;(2-Aminophenyl)-carbamic acid tert-butyl ester;2-(Boc-amino)aniline;N-boc-o-phenylenediamine;Monoboc phenylene diamine;N-Boc-1,2-phenyldiamine;Oprea1_110611;mono-boc-orthophenylenediamine;Mono-N-Boc-o-phenylenediamine;SCHEMBL211033;mono-boc-ortho-phenylenediamine;tert-butyl-2-aminophenylcarbamate;DTXSID60350275;t-butyl (2-aminophenyl)carbamate;Cl-1149;2-(tert-Butoxycarbonylamino)aniline;CS-M2229;N-Boc-1,2-phenylenediamine, 95%;t-butyl (2-amino-phenyl)-carbamate;BBL101204;STL555000;t-butyl N-(2-aminophenyl)-carbamate;tert-butyl (2-amino phenyl)carbamate;AKOS000169541;N-tertbutoxycarbonyl-o-phenylenediamine;MS-1771;N-tert-butoxycarbonyl phenylene diamine;SB77431;N-tert-butoxycarbonyl-o-phenylenediamine;2-Aminophenylcarbamic acid t-butyl ester;1-(t-butoxycarbonylamino)-2-aminobenzene;2-Aminophenyl carbamic acid t-butyl ester;SY030513;n1-(t-butoxycarbonyl)-1,2-benzenediamine;1-(N-t-butoxycarbonylamino)-2-aminobenzene;AM20060866;B4238;FT-0651828;1-(N-t-butyloxycarbonylamino)-2-aminobenzene;1-(N-tert-butoxycarbonylamino)-2-aminobenzene;EN300-40842;N-(tert-Butoxycarbonyl)-1,2-phenylenediamine;(2-amino-phenyl)-carbamic acid tertbutyl ester;(2-amino-phenyl) -carbamic acid tert-butyl ester;A808534;SR-01000308444;J-008237;SR-01000308444-1;Z285919682;Carbamic acid,N-(2-aminophenyl)-,1,1-dimethylethyl ester

Chemical Property of Tert-butyl (2-aminophenyl)carbamate

Chemical Property:

• Vapor Pressure: 0.00375mmHg at 25°C
• Melting Point: 109-114 °C
• Refractive Index: 1.582
• Boiling Point: 280.6 °C at 760 mmHg
• PKA: 13.47±0.70(Predicted)
• Flash Point: 123.5 °C
• PSA: 64.35000
• Density: 1.152 g/cm³
• LogP: 3.27000
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 208.121177757
• Heavy Atom Count: 15
• Complexity: 223

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Boc-1,2-phenyldiamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=CC=CC=C1N
• Uses: Protected 1,2-Phenyldiamine, an intermediate in the synthesis of histone deacetylase agents and antitumor agents.

Technology Process of Tert-butyl (2-aminophenyl)carbamate

There total 19 articles about Tert-butyl (2-aminophenyl)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: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 1,2-diamino-benzene (95-54-5) → tert–butyl (2–aminophenyl)carbamate (146651-75-4)

Guidance literature:

In neat (no solvent); at 80 ℃; for 0.166667h; chemoselective reaction; Green chemistry;

DOI:10.1007/s11164-016-2702-9

Reference yield: 91.0%

(2-nitro-phenyl)-carbamic acid tert-butyl ester (54614-93-6) → tert–butyl (2–aminophenyl)carbamate (146651-75-4)

Guidance literature:

With iron(III) chloride; hydrazine hydrate; In methanol; at 90 ℃; for 3h;

Reference yield: 87.0%

→ tert–butyl (2–aminophenyl)carbamate (146651-75-4)

Guidance literature:

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

1,2-diamino-benzene

di-tert-butyl dicarbonate

{[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile

Downstream raw materials:

C₂₉H₃₃N₅O₆

C₂₃H₃₇N₇O₈

3-[2-(N-tert-Butoxycarbonylamino)anilino]-5-chloro-4H-1,2,6-thiadiazin-4-one

N-(2-N,N-dimethylaminophenyl)-1,1-dimethylethyl ester carbamic acid

Refernces

• 1、 Neisen, Benjamin D.,Solntsev, Pavlo V.,Halvagar, Mohammad R.,Tolman, William B.. "Secondary Sphere Hydrogen Bonding in Monocopper Complexes of Potentially Dinucleating Bis(carboxamide) Ligands". . p. 5856 - 5863. Retrieved 2015.
• 2、 Wang, Yanxin J.,Szantai-Kis, D. Miklos,Petersson, E. James. "Chemoselective modifications for the traceless ligation of thioamide-containing peptides and proteins". . p. 6262 - 6269. Retrieved 2016.
• 3、 Zhang, Zhijun,Han, Xuemei,Wang, Zhimin,Yang, Zhe,Zhang, Wenmin,Li, Juan,Yang, Huanghao,Ling, Xing Yi,Xing, Bengang. "A live bacteria SERS platform for the: In situ monitoring of nitric oxide release from a single MRSA". . p. 7022 - 7025. Retrieved 2018.
• 4、 Ocasio, Cory A.,Sansook, Supojjanee,Jones, Rhiannon,Roberts, Justin M.,Scott, Thomas G.,Tsoureas, Nikolaos,Coxhead, Peter,Guille, Matthew,Tizzard, Graham J.,Coles, Simon J.,Hochegger, Helfrid,Bradner, James E.,Spencer, John. "Pojamide: An HDAC3-Selective Ferrocene Analogue with Remarkably Enhanced Redox-Triggered Ferrocenium Activity in Cells". . p. 3276 - 3283. Retrieved 2017.
• 5、 Li, Shun-Lai,Zhou, Run,Zhao, Wei-Jing,Du, Hong-Guang. "Synthesis of novel acyclic and multiple phenyl iron tetraamino ligand catalysts and its catalytic activity for degradation of dye wastewater by H2O2". . . Retrieved 2021/05/07.
• 6、 Gingrich, Phillip W.,Olson, David E.,Tantillo, Dean J.,Tombari, Robert J.,Tuck, Jeremy R.,Yardeny, Noah. "Calculated oxidation potentials predict reactivity in Baeyer-Mills reactions". supporting information. p. 7575 - 7580. Retrieved 2021/09/22.