tert-Butyl 8-quinolyl carbonate

Base Information

• Chemical Name: tert-Butyl 8-quinolyl carbonate
• CAS No.: 18595-55-6
• Molecular Formula: C14H15 N O3
• Molecular Weight: 245.278
• Hs Code.: 2933499090
• European Community (EC) Number: 242-434-5
• DSSTox Substance ID: DTXSID90171819
• Nikkaji Number: J222.248E
• Wikidata: Q83041968
• Mol file: 18595-55-6.mol

Synonyms:tert-Butyl 8-quinolyl carbonate;18595-55-6;tert-butyl quinolin-8-yl carbonate;EINECS 242-434-5;DTXSID90171819;tert-butyl 8-quinolinyl carbonate;AKOS008227726;Carbonic acid 8-quinolyl tert-butyl ester

Chemical Property of tert-Butyl 8-quinolyl carbonate

Chemical Property:

• Vapor Pressure: 1.21E-05mmHg at 25°C
• Boiling Point: 369.2°Cat760mmHg
• Flash Point: 177.1°C
• PSA: 48.42000
• Density: 1.166g/cm³
• LogP: 3.54870
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 298

Purity/Quality:

98%Min ^*data from raw suppliers

TERT-BUTYL 8-QUINOLINYL CARBONATE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)OC1=CC=CC2=C1N=CC=C2

Technology Process of tert-Butyl 8-quinolyl carbonate

There total 4 articles about tert-Butyl 8-quinolyl 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: 95.0%

8-quinolinol (148-24-3,24804-14-6) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (quinolin-8-yl)carbonate (18595-55-6)

Guidance literature:

With 6,7-dimethoxyisoquinoline; In dichloromethane; at 20 ℃; for 10h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.10.114

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline → tert-butyl (quinolin-8-yl)carbonate (18595-55-6)

Guidance literature:

8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline; With sodium peroxoborate tetrahydrate; In tetrahydrofuran; water; at 20 ℃; for 3h; Inert atmosphere;

di-tert-butyl dicarbonate; With dmap; In tetrahydrofuran; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/asia.201301423

Reference yield:

quinoline (91-22-5) → tert-butyl (quinolin-8-yl)carbonate (18595-55-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tert-butyl methyl ether / 12 h / 60 °C / Inert atmosphere; Glovebox; Sealed tube

2.1: sodium peroxoborate tetrahydrate / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; sodium peroxoborate tetrahydrate; In tetrahydrofuran; tert-butyl methyl ether; water;

DOI:10.1002/asia.201301423

upstream raw materials:

8-quinolinol

di-tert-butyl dicarbonate

quinoline

Downstream raw materials:

L-N-Boc-Ala

t-Boc-L-valine

(S)-N-(tert-butoxycarbonyl)serine

N-tert-butoxycarbonyl-L-leucine

Refernces

• 1、 Saito, Yukako,Yoshimura, Yuichi,Takahata, Hiroki. "Chemoselective O-tert-butoxycarbonylation of phenols using 6,7-dimethoxyisoquinoline as a novel organocatalyst". experimental part. p. 6915 - 6917. Retrieved 2011/03/18.