ChemicalBook > CAS DataBase List > Iodotrimethylsilane

Iodotrimethylsilane

Product Name
Iodotrimethylsilane
CAS No.
16029-98-4
Chemical Name
Iodotrimethylsilane
Synonyms
TRIMETHYLSILYL IODIDE;TMIS;TMS iodide;CT3610;IodotrimethyL;Trimethylsilyl io;Iodotrmethylsilane;trimethyiodosilane;Co-Formula CFS-710;IODOTRIMETHYLSILANE
CBNumber
CB0478159
Molecular Formula
C3H9ISi
Formula Weight
200.09
MOL File
16029-98-4.mol
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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
Specific Gravity
1.47
color 
Clear colorless to reddish
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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
195529
Product name
Iodotrimethylsilane
Purity
97%
Packaging
5g
Price
$48.8
Updated
2024/03/01
Sigma-Aldrich
Product number
195529
Product name
Iodotrimethylsilane
Purity
97%
Packaging
25g
Price
$126
Updated
2024/03/01
TCI Chemical
Product number
I0308
Product name
Trimethylsilyl Iodide (stabilized with Aluminum)
Purity
>95.0%(T)
Packaging
5g
Price
$33
Updated
2024/03/01
TCI Chemical
Product number
I0308
Product name
Trimethylsilyl Iodide (stabilized with Aluminum)
Purity
>95.0%(T)
Packaging
25g
Price
$90
Updated
2024/03/01
Alfa Aesar
Product number
A12902
Product name
Iodotrimethylsilane, 97%, stab. with copper
Packaging
5g
Price
$45
Updated
2024/03/01
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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.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.

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.

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.

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.]

Iodotrimethylsilane Preparation Products And Raw materials

Raw materials

Hexamethyldisiloxane Aluminum

Preparation Products

4-Fluorothiophenol 1-FLUORO-4-(TRIFLUOROMETHYLTHIO)BENZENE (2S)-2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid N,N-DiMethylMethyleneaMMoniuM Iodide 5-Methyl-L-tryptophan
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View Lastest Price from Iodotrimethylsilane manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Iodotrimethylsilane 16029-98-4
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2024-12-06
R&D Scientific Inc.
Product
Trimethylsilyl Iodide 16029-98-4
Price
US $1450.00/Kg
Min. Order
0.100Kg
Purity
98
Supply Ability
500 Kg
Release date
2024-11-18
Hebei Chuanghai Biotechnology Co,.LTD
Product
Iodotrimethylsilane 16029-98-4
Price
US $100.00-50.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20

16029-98-4, IodotrimethylsilaneRelated Search:

N-(Trimethylsilyl)acetamide Trimethylsilyl cyanide Trimethoxysilane tert-Butyldimethylsilyl chloride Methyltris(methylethylketoxime)silane Methyltriacetoxysilane TRIMETHYLSILANE Bromotrimethylsilane 3-Chloropropyltrimethoxysilane Vinyltrimethoxysilane Propidium iodide Isobutyltrimethoxysilane Potassium iodide Azidotrimethylsilane Tetramethylsilane SILANE COUPLING AGENT Trimethoxyphenylsilane (Trifluoromethyl)trimethylsilane

  • IODOTRIMETHYLSILANE
  • IODOTRIMETHYLSILYL IODIDE
  • TMIS
  • CT3610
  • iodotrimethyl-silan
  • Silane, iodotrimethyl-
  • trimethyliodosilane(tmis)
  • TRIMETHYLIODOSILANE
  • TRIMETHYLSILYL IODIDE
  • Iodotrmethylsilane
  • TMS iodide
  • Trimethyliodosilanestabilizedwithcoppergranules
  • IODOTRIMETHYLSILANE , STABILIZED WITH COPPER
  • IODO TRIMETHYL SILYL
  • trimethyiodosilane
  • Iodotrimethylsilane, 97%, stab. with copper
  • Trimethylsilyl Iodide (stabilized with Aluminum)
  • IODOTRIMETHYLSILANE, STAB.
  • Iodotrimethylsilane, stabilised with copper, 95%
  • Iodotrimethylsilane, stabilized, 95-97%
  • Trimethyl iodo silane Iodotrimethylsilane
  • Iodotrimethylsilane, 95+%, packaged under Argon in resealable ChemSeal bottles
  • TMIS, Trimethyliodosilane
  • Iodotrimethylsilane, 95-97%, stabilized
  • Iodotrimethylsilane, stabilized
  • Iodotrimethylsilane ,95% [stabilized with copper]
  • Iodotrimethylsilane, stabilized, AcroSeal, 95-97%
  • TriMethyl silane iodine
  • IodotriMethylsilane, 95-97%, stabilized, AcroSeal
  • IodotriMethylsilane, stabilized, 95-97% 100ML
  • Trimethylsilysiodide
  • IodotriMethylsilane, stabilized, 95-97% 25ML
  • IodotriMethylsilane, stabilized, 95-97% 5ML
  • IodotriMethylsilane, stabilized, AcroSeal, 95-97% 100ML
  • Iodotrimethylsilane Trimethyliodosilane
  • IODOTRIMETHYLSILANE FOR SYNTHESIS
  • Trimethylsilyl iodide, TMIS
  • IodotriMethylsilane (>90%)
  • Three Methyl iodide silane
  • Iodotrimethylsilane, 97%, stabilized
  • Iodotrimethylsilane, 95-97%
  • Iodotrimethylsilane, 1.0 M solution in methylene chloride
  • Iodotrimethylsilane, 98%, stabilized with copper, J&KSeal
  • IodotrimethyL
  • IodotriMethylsilane, stabilized, AcroSeal
  • Trimethylsilyl io
  • Co-Formula CFS-710
  • Trimethylsilyl iodide（TMSI)
  • Iodotrimethylsilane, TMIS
  • TrimethylsilylIodide(stabilizedwithAluminum)&gt
  • trimethyl iodide silane
  • Iodotrimethylsilane, 95-97%, stabilized, AcroSeal&trade
  • lodotrimethylsilane
  • 16029-98-4
  • 1302039
  • C3H9Sil
  • CH33SiI
  • C3H9ISi