Iodotrimethylsilane Property

Melting point:

<0°C

Boiling point:

106 °C(lit.)

Density 

1.406 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.471(lit.)

Flash point:

−25 °F

storage temp. 

-20°C

solubility 

reacts

form 

Liquid

color 

Clear colorless to reddish

Specific Gravity

1.47

Water Solubility 

reacts

Sensitive 

Moisture & Light Sensitive

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

BRN 

1731136

Stability:

Moisture Sensitive (Reactive)

InChIKey

CSRZQMIRAZTJOY-UHFFFAOYSA-N

CAS DataBase Reference

16029-98-4(CAS DataBase Reference)

NIST Chemistry Reference

Iodotrimethylsilane(16029-98-4)

EPA Substance Registry System

Silane, iodotrimethyl- (16029-98-4)

Safety

Hazard Codes 

F,C

Risk Statements 

11-14-34

Safety Statements 

16-26-36/37/39-43-45-25

RIDADR 

UN 2924 3/PG 2

WGK Germany 

3

F 

8-21

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29310095

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Iodotrimethylsilane Chemical Properties,Usage,Production

Chemical Properties

Straw liquid

Uses

Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.

Preparation

Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.

Application

Iodotrimethylsilane can be used as a versatile reagent for the mild dealkylation of ethers, carboxylic esters, lactones, carbamates, acetals, phosphonate and phosphate esters; cleavage of epoxides, cyclopropyl ketones; conversion of vinyl phosphates to vinyl iodides; neutral nucleophilic reagent for halogen exchange reactions, carbonyl and conjugate addition reactions; use as a trimethylsilylating agent for formation of enol ethers, silyl imino esters, and N-silylenamines, alkyl, alkenyl and alkynyl silanes; Lewis acid catalyst for acetal formation, α- alkoxymethylation of ketones, for reactions of acetals with silyl enol ethers and allylsilanes; reducing agent for epoxides, enediones, α-ketols, sulfoxides, and sulfonyl halides; dehydrating agent for oximes.

Reactions

Trimethylsilyl iodide reacts under mild conditions in the absence of a catalyst with alkyl fluorides as well as with benzyl and tertiary alkyl chlorides and bromides to give good yields of alkyl iodides and the corresponding trimethylsilyl halides.

General Description

Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

Synthesis

This procedure describes a convenient method for the preparation of Iodotrimethylsilane: A 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60°C as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°C, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140°C to 210°C, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°C.

Purification Methods

Add a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]