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Perchloryl fluoride

Perchloryl fluoride
Perchloryl fluoride
Perchloryl-fluoride-3D-vdW.png
Names
IUPAC name
Perchloryl fluoride
Other names
Chlorine oxyfluoride, Perchlorofluoride, Chlorine fluorine oxide, Trioxychlorofluoride, Perchloric acid fluoride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.660
EC Number 231-526-0
PubChem CID
RTECS number SD1925000
Properties
ClO3F
Molar mass 102.4496 g/mol
Appearance Colorless gas
Odor sweet odor
Density 1.434 g/cm3
Melting point −147.8 °C (−234.0 °F; 125.3 K)
Boiling point −46.7 °C (−52.1 °F; 226.5 K)
0.06 g/100 ml (20 °C)
Vapor pressure 10.5 atm (20°C)
Viscosity 3.91 x 10−3 Pa.s (@ melting point)
Structure
Tetrahedral
Thermochemistry
−5.7
Hazards
Main hazards Corrosive, oxidizing, toxic
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g., fluorine Special hazard OX: Oxidizer. E.g., potassium perchlorateNFPA 704 four-colored diamond
3 ppm
Lethal dose or concentration (LD, LC):
385 ppm (rat, 4 hr)
451 ppm (dog, 4 hr)
2000 ppm (rat, 40 min)
451 ppm (dog, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 3 ppm (13.5 mg/m3)
REL (Recommended)
 TWA 3 ppm (14 mg/m3) ST 6 ppm (28 mg/m3)
IDLH (Immediate danger)
 100 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3F. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

In spite of its small enthalpy of formation (ΔHfO = −5.7), it is stable, decomposing only at 400 °C. It is quite reactive towards reducing agents and anions, however, with the chlorine atom acting as an electrophile. It reacts explosively with reducing agents such as amides, metals, hydrides, etc. Its hydrolysis in water occurs very slowly, unlike that of chloryl fluoride.

Perchloryl fluoride is produced primarily by the fluorination of perchlorates. Antimony pentafluoride is a commonly used fluorinating agent:

ClO
3F reacts with alcohols to produce alkyl perchlorates, which are extremely shock-sensitive explosives. Using Friedel-Crafts catalysts, it can be used for introducing the –ClO
3 group into aromatic rings via electrophilic aromatic substitution.

Perchloryl fluoride is used in organic chemistry as a mild fluorinating agent. It was the first industrially relevant electrophilic fluorinating agent, used since the 1960s for producing fluorinated steroids. In the presence of aluminum trichloride, it has also been used as a electrophilic perchlorylation reagent for aromatic compounds.


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