Methyl 3-chlorocyclobutanecarboxylate

Base Information

• Chemical Name: Methyl 3-chlorocyclobutanecarboxylate
• CAS No.: 15963-46-9
• Molecular Formula: C6H9ClO2
• Molecular Weight: 148.589
• Hs Code.: 2916209090
• DSSTox Substance ID: DTXSID40550392
• Mol file: 15963-46-9.mol

Synonyms:Methyl 3-chlorocyclobutanecarboxylate;15963-46-9;METHYL 3-CHLOROCYCLOBUTANE-1-CARBOXYLATE;177498-41-8;Cyclobutanecarboxylic acid, 3-chloro-, methyl ester;MFCD16657507;methyl 3-chlorocyclobutane-1-carboxylate, cis;Rel-methyl (1s,3s)-3-chlorocyclobutane-1-carboxylate;starbld0036259;3-Chlorocyclobutanecarboxylic acid methyl ester;SCHEMBL15462227;DTXSID40550392;PYLWYAGIWDJBMC-UHFFFAOYSA-N;AMY34166;AKOS016005536;PB19451;DS-18303;SY029205;CS-0043992;EN300-140109;EN300-252500;A846253;methyl (1s,3s)-3-chlorocyclobutane-1-carboxylate

Chemical Property of Methyl 3-chlorocyclobutanecarboxylate

Chemical Property:

• Vapor Pressure: 0.7mmHg at 25°C
• Boiling Point: 185.358oC at 760 mmHg
• Flash Point: 77.051oC
• PSA: 26.30000
• Density: 1.184g/cm3
• LogP: 1.17680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.0291072
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

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

Methyl3-Chlorocyclobutanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(C1)Cl

Technology Process of Methyl 3-chlorocyclobutanecarboxylate

There total 13 articles about Methyl 3-chlorocyclobutanecarboxylate 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: 68.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-chlorocyclobutane-1-carboxylic acid (35207-71-7) → 3-chlorocyclobutanecarboxylic acid methyl ester (15963-46-9,177498-41-8,177498-42-9)

Guidance literature:

DOI:10.1021/jo00392a047

Reference yield:

cyclobutane-1,1'-dicarboxylic acid (5445-51-2) → 3-chlorocyclobutanecarboxylic acid methyl ester (15963-46-9,177498-41-8,177498-42-9)

Guidance literature:

Multi-step reaction with 3 steps

1: SO₂Cl

2: 20 °C

3: 68 percent

With sulfuryl dichloride;

DOI:10.1021/jo00392a047

Reference yield:

methanol (67-56-1) + 3-chlorocyclobutanecarbonitrile (20249-18-7) → 3-chlorocyclobutanecarboxylic acid methyl ester (15963-46-9,177498-41-8,177498-42-9)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction; 1.) reflux, 1 h, 2.) reflux, 22 h;

DOI:10.1021/ja960370g

upstream raw materials:

diazomethane

3-chlorocyclobutane-1-carboxylic acid

methanol

3-chlorobicyclobutane-1-carbonitrile

Downstream raw materials:

3-chlorocyclobutanemethanol

cis-3-aminocyclobutane-1-carboxylic acid

(1r,3r)-3-aminocyclobutane-1-carboxylic acid

methyl (1r,3r)-3-aminocyclobutane-1-carboxylate

Refernces

• 1、 Li, Gang,Dilger, Andrew K.,Cheng, Peter T.,Ewing, William R.,Groves, John T.. "Selective C?H Halogenation with a Highly Fluorinated Manganese Porphyrin". . p. 1251 - 1255. Retrieved 2018.
• 2、 Radchenko, Dmytro S.,Tkachenko, Anton,Grygorenko, Oleksandr O.,Komarov, Igor V.. "Expedient synthesis of cis- and trans-3-aminocyclobutanecarboxylic acids". . p. 1644 - 1649. Retrieved 2011/06/23.