666-16-0

Basic information

• Product Name: fluorocyclobutane
• CAS NO: 666-16-0
• Molecular Formula: C₄H₇F
• Molecular Weight: 74.0968
• Mol File: 666-16-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 33.846°C at 760 mmHg
• Flash Point: -38.941°C
• Density: 0.915g/cm³
• Vapor Pressure: 553.212mmHg at 25°C
• Refractive Index: 1.377
• CAS DataBase Reference: fluorocyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: fluorocyclobutane(666-16-0)
• EPA Substance Registry System: fluorocyclobutane(666-16-0)

Safety Data

• Hazardous Substances Data: 666-16-0(Hazardous Substances Data)

Usage

General Description

Fluorocyclobutane is a chemical compound with the molecular formula C4H7F. It is a fluorinated derivative of cyclobutane, with a four-membered ring containing one fluorine atom. It is a colorless, flammable gas with a faint odor, and is primarily used as a refrigerant in propellant and blowing agent applications. Fluorocyclobutane has low toxicity and is considered to have low environmental impact. It is also used in the production of pharmaceuticals, agrochemicals, and specialty chemicals due to its stability and reactivity. Additionally, it is being researched for its potential applications in the development of new materials and technologies.

Upstream product

• 1003-13-0 cyclopropylmethyl methyl ether 
• 822-35-5 cyclobutene 
• 1120-57-6 chlorocyclobutane 
• 1015-45-8 cyclopropylmethyl tosylate 
• 2919-23-5 cyclobutanol 
• 33574-02-6 cyclopropylmethyl iodide 

Downstream Products

• 118523-82-3 1-chloro-1-fluorocyclobutane 
• 145801-44-1 trans-1-chloro-3-fluorocyclobutane 
• 145801-45-2 cis-1-chloro-3-fluorocyclobutane 

Relevant articles and documents

Conformational stability, r0 structural parameters, and vibrational assignments of mono-substituted cyclobutanes: Fluorocyclobutane

Variable temperature (-55 to -100 °C) studies of the infrared spectra (3500-400 cm-1) of fluorocyclobutane, c-C4H7F, dissolved in liquid xenon have been carried out as well as the infrared spectra of the gas. By utilizing eight pairs of conformers at 10 different temperatures, the enthalpy difference between the more stable equatorial conformer and the axial form has been determined to be 496 ± 40 cm-1 (5.93 ± 0.48 kJ/mol). The percentage of the axial conformer present at ambient temperature is estimated to be 8 ± 1%. The ab initio MP2(full) average predicted energy difference from a variety of basis sets is 732 ± 47 cm-1 (9.04 ± 0.44 kJ/mol) and the average value of 602 ± 20 cm-1 from density functional theory predictions by the B3LYP method are significantly larger than the experimentally determined enthalpy value. By utilizing previously reported microwave rotational constants for the equatorial and axial conformers combined with ab initio MP2(full)/6-311+G(d,p) predicted structural values, adjusted r0 parameters have been obtained. The determined heavy atom structural parameters for the equatorial [axial] conformer are: distances () C-F = 1.383(3) [1.407(3)], Cα-Cβ = 1.543(3) [1.546(3)], C β-Cγ = 1.554(3) [1.554(3)] and angles (°) ∠CαCβCγ = 85.0(5) [89.2(5)], ∠CβCαCβ = 89.3(5) [89.2(5)], ∠F-(CβCαC β) = 117.4(5) [109.2(5)] and a puckering angle of 37.4(5) [20.7(5)]. The conformational stabilities, harmonic force fields, infrared intensities, Raman activities, depolarization ratios and vibrational frequencies have been obtained for both conformers from MP2(full)/6-31G(d) ab initio calculations and compared to experimental values where available. The results are discussed and compared to the corresponding properties of some other monosubstituted cyclobutanes with halogen and pseudo-halogen substituents.

Rearrangement and double fluorination in the deiodinative fluorination of neopentyl iodide with xenon difluoride

Alkyl iodides give products from the neopentyl rearrangement on reaction with xenon difluoride. Neopentyl iodide performs a double rearrangement and yields a gem-difluoro product, 2,2-difluoro-3-methylbutane. Studies of the mechanism show that an alkene intermediate is involved in the double rearrangement process. Alkenes can be substituted as substrates in reaction with xenon difluoride-iodine to give gem-difluoro products. 13C Labeling verifies the skeletal rearrangement process.