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Iodotrimethylsilane

Description Uses Preparation
Iodotrimethylsilane
Iodotrimethylsilane structure
CAS No.
16029-98-4
Chemical Name:
Iodotrimethylsilane
Synonyms
TMIS;CT3610;TMS iodide;IodotrimethyL;Trimethylsilyl io;trimethyiodosilane;Iodotrmethylsilane;Co-Formula CFS-710;IODOTRIMETHYLSILANE;TRIMETHYLIODOSILANE
CBNumber:
CB0478159
Molecular Formula:
C3H9ISi
Formula Weight:
200.09
MOL File:
16029-98-4.mol

Iodotrimethylsilane Properties

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
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
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS05
Signal word  Danger
Hazard statements  H225-H314-H318
Precautionary statements  P260h-P303+P361+P353-P501a-P233-P240-P241+P242+P243-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405-P501-P210-P280-P305+P351+P338-P310
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
8-21
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29310095
NFPA 704
3
3 2
W

Iodotrimethylsilane price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 195529 Iodotrimethylsilane 97% 16029-98-4 5g $37.8 2019-12-02 Buy
Sigma-Aldrich 195529 Iodotrimethylsilane 97% 16029-98-4 25g $96.6 2019-12-02 Buy
TCI Chemical I0308 Trimethylsilyl Iodide (stabilized with Aluminum) >95.0%(T) 16029-98-4 5g $26 2020-06-24 Buy
TCI Chemical I0308 Trimethylsilyl Iodide (stabilized with Aluminum) >95.0%(T) 16029-98-4 25g $74 2020-06-24 Buy
Alfa Aesar A12902 Iodotrimethylsilane, 97%, stab. with copper 16029-98-4 25g $92.8 2020-06-24 Buy

Iodotrimethylsilane Chemical Properties,Uses,Production

Description

Iodotrimethylsilane which has a hard acid (Me3Si) -soft base (I) bond displays a strong oxygenophilicity towards ethers, esters, lactones, acetals, and other molecules involving oxygen atom as a functional group.
The use of iodotrimethylsilane as the agent brought about a facile cleavage of the tert-butyl ester, giving the corresponding carboxylic acid in excellent yield.
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.
Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.
For the introduction of the TMS group, e.g., TMS enol ethers.
Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.

Uses

Trimethylsilyliodide is a typical blocking agent in pharmaceutical manufacturing, widely used in the syntheses of drugs. It can protect or deprotect functional groups selectively, act as silane blocking agent.

Preparation

Iodotrimethylsilane, prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes.
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.

Chemical Properties

Straw liquid

Uses

Iodotrimethylsilane is an efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage.

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.

Chemical Synthesis

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° 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°, 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° to 210°, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°.

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

Preparation Products


Iodotrimethylsilane Suppliers

Global( 313)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21837 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22625 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1365 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24754 60
Anhui Royal Chemical Co., Ltd.
+86-025-86655873
marketing@royal-chem.com CHINA 537 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30043 58
Win-Win Chemical CO., Limited
0086-577-64498589
0086-577-56994596 sales@win-winchemical.com CHINA 999 58
Kingfirst chemical (nanjing) co.,ltd
86-25-84522992
86-25-84774616 or 1617 marketing@kingfirstchem.com CHINA 95 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23977 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 10154 58

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View Lastest Price from Iodotrimethylsilane manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-12 Iodotrimethylsilane
16029-98-4
US $1.00 / KG 1G 99% 100kg career henan chemical co

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