Tert-butyl (6-fluoropyridin-3-yl)carbamate

Base Information

• Chemical Name: Tert-butyl (6-fluoropyridin-3-yl)carbamate
• CAS No.: 171178-41-9
• Molecular Formula: C10H13FN2O2
• Molecular Weight: 212.22
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID60452602
• Nikkaji Number: J763.327K
• Wikidata: Q72448123
• Mol file: 171178-41-9.mol

Synonyms:171178-41-9;tert-butyl (6-fluoropyridin-3-yl)carbamate;N-Boc-5-amino-2-fluoropyridine;Tert-butyl N-(6-fluoropyridin-3-yl)carbamate;tert-butyl 6-fluoropyridin-3-ylcarbamate;tert-butyl(6-fluoropyridin-3-yl)carbamate;(6-Fluoro-pyridin-3-yl)-carbamic acid tert-butyl ester;SCHEMBL392294;Boc-5-Amino-2-fluoropyridine;3-Boc-amino)-6-fluoro-pyridine;DTXSID60452602;FXGNEIOGSGKPFL-UHFFFAOYSA-N;AB2738;MFCD08274661;AKOS000266691;AM803325;AS-44652;CS-0037503;FT-0752500;EN300-3256829;5-[N-(tert-butoxycarbonyl)amino]-2-fluoropyridine;A811298;(6-Fluoro-3-pyridyl)carbamic acid tert-butyl ester;(6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester

Chemical Property of Tert-butyl (6-fluoropyridin-3-yl)carbamate

Chemical Property:

• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.529
• Boiling Point: 258.294 °C at 760 mmHg
• PKA: 11.91±0.70(Predicted)
• Flash Point: 110.013 °C
• PSA: 51.22000
• Density: 1.207 g/cm³
• LogP: 2.64070
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 212.09610582
• Heavy Atom Count: 15
• Complexity: 228

Purity/Quality:

98%min ^*data from raw suppliers

tert-butylN-(6-fluoropyridin-3-yl)carbamate ^*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=CN=C(C=C1)F

Technology Process of Tert-butyl (6-fluoropyridin-3-yl)carbamate

There total 6 articles about Tert-butyl (6-fluoropyridin-3-yl)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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-fluoro-5-aminopyridine (1827-27-6) → (6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester (171178-41-9)

Guidance literature:

In tert-butyl alcohol; at 40 ℃; for 4h;

DOI:10.1016/j.bmcl.2004.01.034

Reference yield: 65.0%

5-bromo-2-fluoropyridine (766-11-0) + tert-butyl carbazate (4248-19-5) → (6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester (171178-41-9)

Guidance literature:

With (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine; In acetonitrile; at 23 ℃; for 48h; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.8b02182

Reference yield:

2-Fluoro-5-nitropyridine (456-24-6) → (6-fluoro-pyridin-3-yl)-carbamic acid, tert-butyl ester (171178-41-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / H₂ / Raney Ni / ethyl acetate

2: 96 percent / 2-methyl-propan-2-ol / 4 h / 40 °C

With hydrogen; nickel; In ethyl acetate; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.01.034

upstream raw materials:

di-tert-butyl dicarbonate

2-fluoro-5-aminopyridine

2-Fluoro-5-nitropyridine

2-chloro-5-nitropyridine

Downstream raw materials:

(E)-N-(4-((3-bromo-4-chlorophenyl)amino)pyrido[3,4-d]pyrimidin-6-yl)-4-(dimethylamino)but-2-enamide

4-chloro-6-fluoro-pyrido[3,4-d]pyrimidine

5-[N-(tert-Butoxycarbonyl)-amino]-2-fluoropyridine-4-carboxylic acid

6-fluoro-4-oxo-3H-pyrido[3,4-d]pyrimidine

Refernces

• 1、 -. "SUBSTITUTED HETEROCYCLIC COMPOUNDS AND THERAPEUTIC USES THEREOF". Page/Page column 168-169. . Retrieved 2022/02/09.
• 2、 -. "HETEROCYCLIC INHIBITORS OF TYROSINE KINASE". Paragraph 0292. . Retrieved 2020/11/03.