Tert-butyl furan-3-ylcarbamate

Base Information

• Chemical Name: Tert-butyl furan-3-ylcarbamate
• CAS No.: 56267-48-2
• Molecular Formula: C9H13NO3
• Molecular Weight: 183.20442
• Hs Code.: 2932190090
• European Community (EC) Number: 878-834-7
• DSSTox Substance ID: DTXSID20480461
• Nikkaji Number: J1.804.767E
• Wikidata: Q72503239
• Mol file: 56267-48-2.mol

Synonyms:TERT-BUTYL FURAN-3-YLCARBAMATE;56267-48-2;tert-butyl N-(furan-3-yl)carbamate;3-(BOC-AMINO)-FURAN;TERT-BUTYL 3-FURYLCARBAMATE;MFCD09839085;3-(Boc-amino)furan;Carbamic acid, 3-furanyl-, 1,1-dimethylethyl ester;N-boc-3-furanamine;BOC-3-AMINOFURAN;CARBAMIC ACID, 3-FURANYL-, 1,1-DIMETHYLETHYL ESTER (9CI);tert-butylfuran-3-ylcarbamate;SCHEMBL190015;OSM-S-425;DTXSID20480461;SBFLPNJYWRKWFT-UHFFFAOYSA-N;AKOS006328566;AB53464;CS-W009061;AC-29685;DS-10939;SY039806;A8082;FT-0601829;EN300-97484;Z1198234151

Chemical Property of Tert-butyl furan-3-ylcarbamate

Chemical Property:

• Vapor Pressure: 0.251mmHg at 25°C
• Melting Point: 135-137 °C
• Refractive Index: 1.512
• Boiling Point: 205.3 °C at 760 mmHg
• PKA: 13.52±0.70(Predicted)
• Flash Point: 78 °C
• PSA: 51.47000
• Density: 1.136 g/cm³
• LogP: 2.69960
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 183.08954328
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

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

3-Aminofuran, N-Boc protected ^*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=COC=C1

Technology Process of Tert-butyl furan-3-ylcarbamate

There total 3 articles about Tert-butyl furan-3-ylcarbamate 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: 97.0%

3-bromofurane (22037-28-1) + tert-butyl carbazate (4248-19-5) → N-(3-furyl)carbamic acid tert-butyl ester (56267-48-2)

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; at 110 ℃; for 24h;

DOI:10.1016/S0040-4039(02)01725-2

Reference yield: 78.0%

3-Furoic acid (488-93-7) + tert-butyl alcohol (75-65-0) → N-(3-furyl)carbamic acid tert-butyl ester (56267-48-2)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In toluene; at 20 ℃; Reflux;

Reference yield:

3-bromofurane (22037-28-1) + lithium t-butyl N-tosyloxycarbamate → N-(3-furyl)carbamic acid tert-butyl ester (56267-48-2)

Guidance literature:

With n-butyllithium; dimethylsulfide; copper(I) bromide; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 to -60 deg C, 1 h, 3.) THF, hexane, -78 deg C, 2 h;

upstream raw materials:

3-bromofurane

3-Furoic acid

tert-butyl alcohol

tert-butyl carbazate

Downstream raw materials:

ethyl furo[3,2-b]pyridine-6-carboxylate

N-(2-formyl-3-furyl)carbamic acid tert-butyl ester

methyl 3-((tert-butoxycarbonyl)amino)furan-2-carboxylate

Refernces

• 1、 Wu, Zhengyang,Bai, Ying,Jin, Jiaming,Jiang, Teng,Shen, Hui,Ju, Qiurong,Zhu, Qihua,Xu, Yungen. "Discovery of novel and potent PARP/PI3K dual inhibitors for the treatment of cancer". . . Retrieved 2021/03/19.
• 2、 Heffron, Timothy P.,Wei, Binqing,Olivero, Alan,Staben, Steven T.,Tsui, Vickie,Do, Steven,Dotson, Jennafer,Folkes, Adrian J.,Goldsmith, Paul,Goldsmith, Richard,Gunzner, Janet,Lesnick, John,Lewis, Cristina,Mathieu, Simon,Nonomiya, Jim,Shuttleworth, Stephen,Sutherlin, Daniel P.,Wan, Nan Chi,Wang, Shumei,Wiesmann, Christian,Zhu, Bing-Yan. "Rational design of phosphoinositide 3-kinase inhibitors that exhibit selectivity over the phosphoinositide 3-kinase isoform". experimental part. p. 7815 - 7833. Retrieved 2012/01/05.