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Trifluoromethyl iodide

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Related articles

Trifluoromethyl iodide Basic information
Uses Reactions
Product Name:Trifluoromethyl iodide
Synonyms:PERFLUOROMETHYL IODIDE;Freon13I1;freon13t1;iodotrifluoromethane(trifluoromethyliodide);Methane,trifluoroiodo-;monoiodotrifluoromethane;Trifluoromethyl iodide 99%;R13I1
CAS:2314-97-8
MF:CF3I
MW:195.91
EINECS:219-014-5
Product Categories:organofluorine compounds
Mol File:2314-97-8.mol
Trifluoromethyl iodide Structure
Trifluoromethyl iodide Chemical Properties
Melting point <−78 °C(lit.)
Boiling point −22.5 °C(lit.)
density 2.361
vapor pressure 540.5kPa at 25℃
refractive index 1.379
Fp -22.5°C
form Gas
Water Solubility Slightly soluble in water.
Sensitive Light Sensitive
BRN 1732740
Stability:Stable. Substances to be avoided include strong oxidizing agents. Avoid direct sunlight. Risk of explosion if heated under confinement. Flammable.
LogP2.41 at 22.85℃
CAS DataBase Reference2314-97-8(CAS DataBase Reference)
NIST Chemistry ReferenceMethane, trifluoroiodo-(2314-97-8)
EPA Substance Registry SystemTrifluoroiodomethane (2314-97-8)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 68
Safety Statements 36/37
RIDADR UN 1956 2.2
WGK Germany 1
RTECS PB6975000
27
Hazard Note Irritant
TSCA T
HazardClass 2.2
HS Code 2903780020
MSDS Information
ProviderLanguage
Iodotrifluoromethane English
SigmaAldrich English
ALFA English
Trifluoromethyl iodide Usage And Synthesis
Uses

Trifluoroiodomethane is used as a gaseous fire suppression flooding agent for in-flight aircraft and electronic equipment fires. It is also an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals. It is involved in the rhodium-catalyzed alfa-trifluoromethylation of alfa,beta-unsaturatedketones. It plays an important role as catalyst in the enantioselective alfa -trifluoromethylation of aldehydes through photoredox organocatalysis using a readily available iridium photocatalyst.

Reactions

Trifluoromethyl iodide reacts with [AuMeL] to give [AuMe2(CF3)L] and [AuIL](L = PMe3 or PMe2Ph), or [Au(CF3)L] and Mel (L = PPh3), or a mixture of these products (L = PMePh2). In some cases reaction of [AuMe(PMe3)] with CF3I gives [AuMe(CF3)I(PMe3)]. Evidence is presented that the reactions proceed, at least in part, by a free-radical chain mechanism.

Chemical Propertiescolourless gas
UsesReagent used in the rhodium-catalyzed α-trifluoromethylation of α,?-unsaturated ketones.
UsesTrifluoroiodomethane is used as a gaseous fire suppression flooding agent for in-flight aircraft and electronic equipment fires. It is also an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals. It is involved in the rhodium-catalyzed alfa-trifluoromethylation of alfa,beta-unsaturatedketones. It plays an important role as catalyst in the enantioselective alfa -trifluoromethylation of aldehydes through photoredox organocatalysis using a readily available iridium photocatalyst.
Preparation A glass flask provided with a gas outlet is filled with 80 g. (0.153 mole) of CI4 and 30 g. (0.135 mole) of IF5. The gas outlet is connected via short rubber tubes to several gas traps cooled with liquid nitrogen. Agitation of the vessel produces vigorous evolution of gas. When the reaction subsides, the system is heated for 30 min at 90-100°C. The condensate in the gas traps is then washed with 5% NaOH and fractionated. The yield is 90%. preparation of Trifluoromethyl iodide
Synthesis Reference(s)Journal of the American Chemical Society, 107, p. 5014, 1985 DOI: 10.1021/ja00303a042
Flammability and ExplosibilityNot classified
Tag:Trifluoromethyl iodide(2314-97-8) Related Product Information
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