Tert-butyl 4-fluoro-3-nitrophenylcarbamate

Base Information

• Chemical Name: Tert-butyl 4-fluoro-3-nitrophenylcarbamate
• CAS No.: 332370-72-6
• Molecular Formula: C11H13FN2O4
• Molecular Weight: 256.234
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID00455899
• Wikidata: Q82278058
• Mol file: 332370-72-6.mol

Synonyms:332370-72-6;TERT-BUTYL 4-FLUORO-3-NITROPHENYLCARBAMATE;TERT-BUTYL N-(4-FLUORO-3-NITROPHENYL)CARBAMATE;tert-butyl (4-fluoro-3-nitrophenyl)carbamate;543708-58-3;Propanamide, N-(4-fluoro-3-nitrophenyl)-2,2-dimethyl-;TERT-BUTYL4-FLUORO-3-NITROPHENYLCARBAMATE;SCHEMBL1885546;DTXSID00455899;AEIHOUCJAIZEFV-UHFFFAOYSA-N;AKOS014313136;AB44743;AT33365;BS-25230;CS-0208920;EN300-84831;(4-Fluoro-3-nitro-phenyl)-carbamic acid tert-butyl ester

Chemical Property of Tert-butyl 4-fluoro-3-nitrophenylcarbamate

Chemical Property:

• PSA: 84.15000
• LogP: 3.67710
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 256.08593506
• Heavy Atom Count: 18
• Complexity: 324

Purity/Quality:

98%min ^*data from raw suppliers

(4-Fluoro-3-nitrophenyl)carbamic acid tert-butyl ester 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=CC(=C(C=C1)F)[N+](=O)[O-]

Technology Process of Tert-butyl 4-fluoro-3-nitrophenylcarbamate

There total 5 articles about Tert-butyl 4-fluoro-3-nitrophenylcarbamate 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: 93.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-Fluoro-3-nitroaniline (364-76-1) → N-(tert-butoxycarbonyl)-4-fluoro-3-nitroaniline (332370-72-6)

Guidance literature:

In tetrahydrofuran; for 48.5h; Reflux; Inert atmosphere;

Reference yield:

4-Fluorobenzoic acid (456-22-4) → N-(tert-butoxycarbonyl)-4-fluoro-3-nitroaniline (332370-72-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / KNO₃; conc. H₂SO₄ / 20 °C

2: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

3: sodium azide / CH₂Cl₂; dimethylformamide / 20 °C

4: CH₂Cl₂; dimethylformamide / Heating

With sodium azide; oxalyl dichloride; sulfuric acid; potassium nitrate; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0205090

Reference yield:

3-nitro-4-fluorobenzoic acid (453-71-4) → N-(tert-butoxycarbonyl)-4-fluoro-3-nitroaniline (332370-72-6)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride; DMF / CH₂Cl₂ / 20 °C

2: sodium azide / CH₂Cl₂; dimethylformamide / 20 °C

3: CH₂Cl₂; dimethylformamide / Heating

With sodium azide; oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm0205090

upstream raw materials:

di-tert-butyl dicarbonate

4-Fluoro-3-nitroaniline

4-Fluorobenzoic acid

3-nitro-4-fluorobenzoic acid

Downstream raw materials:

1-(3-amino-4-fluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

ethyl 1-(3-tert-butoxycarbonylamino-4-fluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Refernces

• 1、 -. "INHIBITOR OF BTK AND MUTANTS THEREOF". Page/Page column 233. . Retrieved 2020/09/12.
• 2、 Huggins, William M.,Vu Nguyen,Hahn, Nicholas A.,Baker, James T.,Kuo, Laura G.,Kaur, Darpan,Melander, Roberta J.,Gunn, John S.,Melander, Christian. "2-Aminobenzimidazoles as antibiofilm agents against Salmonella enterica serovar Typhimurium". supporting information. p. 1547 - 1552. Retrieved 2018/10/02.