22082-78-6

Basic information

• Product Name: Trifluoromethyl hypochlorite
• Synonyms: Trifluoromethyl hypochlorite
• CAS NO: 22082-78-6
• Molecular Formula: CClF₃O
• Molecular Weight: 120.4583096
• Mol File: 22082-78-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: -46.99°C (rough estimate)
• Appearance: /
• CAS DataBase Reference: Trifluoromethyl hypochlorite(CAS DataBase Reference)
• NIST Chemistry Reference: Trifluoromethyl hypochlorite(22082-78-6)
• EPA Substance Registry System: Trifluoromethyl hypochlorite(22082-78-6)

Safety Data

• Hazardous Substances Data: 22082-78-6(Hazardous Substances Data)

Usage

General Description

Trifluoromethyl hypochlorite is a highly reactive inorganic compound with the chemical formula CF3OCl. It is a colorless gas or liquid at room temperature and is primarily used as a reagent in organic synthesis, particularly in the introduction of trifluoromethyl groups into molecules. Trifluoromethyl hypochlorite is a strong oxidizing agent and can react violently with a wide range of organic compounds, making it a potentially hazardous material to handle. Proper precautions should be taken when working with this chemical, including wearing appropriate protective equipment and conducting reactions in a well-ventilated area.

Upstream product

• 16566-10-2 Fluorocarbonyl hypofluorite 
• 353-50-4 Carbonyl fluoride 
• 7790-89-8 chlorine monofluoride 

Downstream Products

• 1645-95-0 1-chloro-2-(trifluoromethoxy)ethane 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 1493-11-4 trifluoromethanol 
• 338-65-8 1-chloro-2,2-difluoroethane 
• 84011-37-0 2-Chloro-1-fluoro-1-trifluoromethoxy-ethane 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 25957-33-9 Trifluormethyl-1,1-difluor-2-chloraethylaether 
• 151-67-7 1,1,1-trifluoro-2-bromo-2-chloroethane 
• 84011-25-6 2-Bromo-2-chloro-1,1-difluoro-1-trifluoromethoxy-ethane 
• 353-50-4 Carbonyl fluoride 
• 84011-40-5 cis-1-Chloro-2-(trifluoromethoxy)cyclohexane 
• 421-14-7 methyltrifluoromethyl ether 
• 21811-29-0 trifluoroketone 
• 75-72-9 chlorotrifluoromethane 

Relevant articles and documents

From hypochlorites to perfluorinated dialkyl peroxides

The synthesis and characterization of the new perfluorinated hypochlorite, undecafluoro-tert-pentyl hypochlorite, (C2F5)(F3C)2COCl, is reported. Its gas-phase infrared, UV/Vis and NMR spectra have been recorded and its spectroscopic properties are discussed and compared with quantum-chemical predictions and those of other known perfluorinated hypochlorites such as RFOCl [RF = F3C, (F3C)3C, (C2F5)(F3C)2C]. A synthetic route to otherwise difficult to access perfluorinated dialkyl peroxides, RFOORF, is also provided by low-temperature photolysis of the corresponding hypochlorite.

A photoionization study of trifluoromethanol, CF3OH, trifluoromethyl hypofluorite, CF3OF, and trifluoromethyl hypochlorite, CF3OCl

CF3OH, an important and controversial by-product of atmospheric decomposition of CF3CFH2 (HFC-134a) and other hydrofluorocarbons, has been examined by photoionization mass spectrometry. The ionization onset is characterized by a broad Franck-Condon distribution, arising primarily from a substantial elongation of the C-O bond upon ionization. An upper limit to the adiabatic ionization potential (IP) of ≤ 13.08 ± 0.05 eV has been established. The appearance potentials (APs) of the first two fragments have been accurately determined by fitting with appropriate model functions as AP0(CF2OH+/CF 3OH)≤13.830±0.005 eV and AP0(CF+3/CF 3OH)≤13.996±0.005 eV. While the exact nature of the lowest-energy fragment (nominally CF2OH+) is not clear, the CF+3 fragment threshold leads unambiguously to ΔH°f 298(CF3OH)≥-217.2±0.9 kcal/mol and D298(CF3-OH)≤115.2±0.3 kcal/mol. With previously derived ΔH°f 298(CF3O)=-151.8+1.7-1.1 kcal/mol, this yields D298(CF3O-H) =117.5+1.9-1.4 kcal/mol, very close to, or only slightly weaker than the O-H bond energy in water: D298(CF3O-H)-D298(HO-H)=-1.8 +1.9-1.4 kcal/mol≈0 kcal/mol. Similarly, with the recently redetermined value for ΔH°f(CF2O), this implies a 298 K reaction enthalpy for the 1,2-elimination of HF from CF3OH of 2.81+1.7-1.1 kcal/mol. CF3OF and CF3OCl have also been examined by photoionization. CF3OF produces a very weak parent, with an apparent adiabatic IP(CF3OF) ≤12.710±0.007 eV. An analysis of the CF+3 and CF2O+ fragments from CF3OF, when combined with literature data, suggests ΔH°f 298(CF3OF)=-176.9+1.8-1.3 kcal/mol. The fitted value for the appearance potential of CF+3 from CF3OCl, AP0(CF+3/CF 3OCl)≤12.85±0.01 eV, leads to ΔH°f 298(CF3OCl)≥-175.6±1.0 kcal/mol, D298(CF3-OCl)≤88.4±0.3 kcal/mol, and D298(CF3O-Cl)≤52.8+2.0-1.5 is kcal/mol.