Iodotrimethylsilane

ChemicalBook > CAS DataBase List > 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