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

Flash point:

-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.

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 

T

HazardClass 

2.2

HS Code 

2903780020

MSDS

• Language:English Provider:Iodotrifluoromethane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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 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%.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 5014, 1985 DOI: 10.1021/ja00303a042

Flammability and Explosibility

Not classified

Trifluoromethyl iodide(2314-97-8)Related Product Information

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