2,2-difluorocyclobutanecarboxylic acid

Base Information

• Chemical Name: 2,2-difluorocyclobutanecarboxylic acid
• CAS No.: 1150518-74-3
• Molecular Formula: C5H6F2O2
• Molecular Weight: 136.098
• Mol file: 1150518-74-3.mol

Synonyms:2,2-difluorocyclobutanecarboxylic acid;Cyclobutanecarboxylic acid, 2,2-difluoro-

Chemical Property of 2,2-difluorocyclobutanecarboxylic acid

Chemical Property:

• Boiling Point: 204.7±40.0 °C(Predicted)
• PKA: 3.29±0.40(Predicted)
• PSA: 37.30000
• Density: 1.37±0.1 g/cm3(Predicted)
• LogP: 1.11630

Purity/Quality:

≥99% ^*data from raw suppliers

2,2-Difluorocyclobutane-1-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,2-difluorocyclobutanecarboxylic acid

There total 4 articles about 2,2-difluorocyclobutanecarboxylic acid 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: 98.0%

racemic (2,2-difluorocyclobutyl)methanol (1419101-11-3) → 2,2-difluorocyclobutanecarboxylic acid (1150518-74-3)

Guidance literature:

With sodium periodate; rhodium(III) chloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.9b00719

Reference yield: 74.0%

(2,2-difluorocyclobutyl)benzene → 2,2-difluorocyclobutanecarboxylic acid (1150518-74-3)

Guidance literature:

With sodium periodate; ruthenium(III)chloride; In tetrachloromethane; acetonitrile; at 20 ℃; for 24h; Solvent;

Reference yield:

(2-oxocyclobutyl)methyl acetate (73680-15-6) → 2,2-difluorocyclobutanecarboxylic acid (1150518-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: morpholinosulfur trifluoride / dichloromethane / 48 h / 20 °C

2: sodium hydroxide / water / 0.5 h / Reflux

3: sodium periodate; rhodium(III) chloride hydrate / acetonitrile; water; tetrachloromethane / 2 h / 20 °C

With sodium periodate; rhodium(III) chloride hydrate; morpholinosulfur trifluoride; sodium hydroxide; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/acs.joc.9b00719

upstream raw materials:

(2-oxocyclobutyl)methyl acetate

racemic (2,2-difluorocyclobutyl)methanol

Downstream raw materials:

C₂₉H₃₉F₂N₅O₃

C₃₁H₄₃F₂N₅O₂

Refernces

• 1、 Lin, Peng-Peng,Huang, Long-Ling,Feng, Si-Xin,Yang, Shuang,Wang, Honggen,Huang, Zhi-Shu,Li, Qingjiang. "Gem-Difluorination of Methylenecyclopropanes (MCPs) Featuring a Wagner-Meerwein Rearrangement: Synthesis of 2-Arylsubstituted gem-Difluorocyclobutanes". supporting information. p. 3088 - 3093. Retrieved 2021/05/05.