ChemicalBook Product Catalog Chemical Reagents Organic reagents Halogenated aliphatic hydrocarbons Trifluoromethyl iodide

Trifluoromethyl iodide

Product NameTrifluoromethyl iodide
CAS2314-97-8
MFCF3I
MW195.91
EINECS219-014-5
MOL File2314-97-8.mol

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
Flash point	-22.5°C
form	Gas
Water Solubility	Slightly soluble in water.
Specific Heat Capacity	Cp(gas): 0.36 J/(g·K), at 25℃
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.
InChI	1S/CF3I/c2-1(3,4)5
InChIKey	VPAYJEUHKVESSD-UHFFFAOYSA-N
SMILES	FC(F)(F)I
LogP	2.41 at 22.85℃
CAS DataBase Reference	2314-97-8(CAS DataBase Reference)
NIST Chemistry Reference	Methane, trifluoroiodo-(2314-97-8)
EPA Substance Registry System	Trifluoroiodomethane (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
F	27
Hazard Note	Irritant
TSCA	TSCA listed
HazardClass	2.2
HS Code	2903780020
Storage Class	2A - Gases
Hazard Classifications	Muta. 2 Ozone 1 Press. Gas Compr. Gas

MSDS

Provider	Language
Iodotrifluoromethane	English
SigmaAldrich	English
ALFA	English

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 Properties

Trifluoromethyl iodide is a colourless gas, it is stable under normal temperatures and pressure. However, upon decomposition, it may form acid halides such as hydrogen fluoride (HF) and hydrogen iodide. It is incompatible with oxidizing materials.

Uses

Reagent used in the rhodium-catalyzed α-trifluoromethylation of α,-unsaturated ketones.

Preparation

Trifluoromethyl iodide's synthesis method: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