5-amino-2,4-di-tert-butylphenyl methyl carbonate

Base Information

• Chemical Name: 5-amino-2,4-di-tert-butylphenyl methyl carbonate
• CAS No.: 1182822-31-6
• Molecular Formula: C16H25NO3
• Molecular Weight: 279.379
• Hs Code.: 2922199090
• Mol file: 1182822-31-6.mol

Synonyms:5-amino-2,4-di-tert-butylphenyl methyl carbonate;QC-4868;

Chemical Property of 5-amino-2,4-di-tert-butylphenyl methyl carbonate

Chemical Property:

• Boiling Point: 372 oC
• PKA: 3.07±0.10(Predicted)
• Flash Point: 116 oC
• PSA: 61.55000
• Density: 1.038
• LogP: 4.59020
• Storage Temp.: 2-8°C

Purity/Quality:

99.9% ^*data from raw suppliers

5-Amino-2,4-di-tert-butylphenylmethylcarbonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-amino-2,4-di-tert-butylphenyl methyl carbonate

There total 6 articles about 5-amino-2,4-di-tert-butylphenyl methyl carbonate 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: 29.0%

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester (873055-55-1) → 5-amino-2,4-di-tert-butylphenyl methyl carbonate (1182822-31-6)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In ethanol; for 2h; Reflux;

DOI:10.1016/j.bmcl.2014.10.071

Reference yield:

5-amino-2-4-di-tert-butyl-phenol (873055-58-4) + methyl chloroformate (79-22-1) → 5-amino-2,4-di-tert-butylphenyl methyl carbonate (1182822-31-6)

Guidance literature:

With triethylamine; In diethyl ether; at 0 - 20 ℃;

Reference yield:

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester (873055-54-0) → 5-amino-2,4-di-tert-butylphenyl methyl carbonate (1182822-31-6)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid; sulfuric acid / 1 h / 0 - 20 °C

2: hydrogen / 5%-palladium/activated carbon / methanol / 20 - 30 °C / 1500.15 Torr / Inert atmosphere

With sulfuric acid; hydrogen; nitric acid; 5%-palladium/activated carbon; In methanol;

upstream raw materials:

carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester

2,4-di-tert-Butylphenol

carbonic acid 2,4-di-tert-butyl-phenyl ester methyl ester

2,4-di-tert-butyl-5-nitro-phenol

Downstream raw materials:

2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate

ivacaftor

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

Refernces

• 1、 Lewandowski, Bérénice L.,Looker, Adam R.,Roeper, Stefanie,Ryan, Michael P.,Wilde, Nathan,Ye, Zhifeng. "Utilizing o-Quinone Methide Chemistry: Synthesis of d9-Ivacaftor". . . Retrieved 2020/01/22.
• 2、 -. "Industrial Process for Making an Ivacaftor and its Intermediates". . . Retrieved 2017/04/23.