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Iodotrimethylsilane structure
Iodotrimethylsilane structure

Iodotrimethylsilane

Iupac Name:iodo(trimethyl)silane
CAS No.: 16029-98-4
Molecular Weight:200.094
Modify Date.: 2022-11-08 17:07
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
Iodotrimethylsilane
1.2 Synonyms

EINECS 240-171-0 Iodo(trimethyl)silane Me3SiI MFCD00001028 Silane, iodotrimethyl- TMS iodide TMSI Trimethyliodosilane Trimethylsilyl iodide

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1.3 CAS No.
16029-98-4
1.4 CID
85247
1.5 EINECS(EC#)
240-171-0
1.6 Molecular Formula
C3H9ISi (isomer)
1.7 Inchi
InChI=1S/C3H9ISi/c1-5(2,3)4/h1-3H3
1.8 InChIkey
CSRZQMIRAZTJOY-UHFFFAOYSA-N
1.9 Canonical Smiles
C[Si](C)(C)I
1.10 Isomers Smiles
C[Si](C)(C)I
2. Properties
2.1 Density
1.406
2.1 Melting point
<0°C
2.1 Boiling point
106℃
2.1 Refractive index
1.47-1.48
2.1 Flash Point
-31℃
2.1 Precise Quality
199.95200
2.1 PSA
0.00000
2.1 logP
2.25630
2.1 Solubility
reacts
2.2 Appearance
Clear very slight brown liquid.
2.3 Storage
Store at -20°C. Moisture Sensitive. Light Sensitive. Store under Nitrogen.
2.4 Chemical Properties
Straw liquid
2.5 Color/Form
Clear colorless to reddish
2.6 Water Solubility
reacts
2.7 StorageTemp
?20°C
3. Use and Manufacturing
3.1 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 Preparation Products
3.2 Usage
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.
4. Safety and Handling
4.1 Symbol
GHS02, GHS05
4.1 Hazard Codes
C
4.1 Signal Word
Danger
4.1 Risk Statements
R11;R34
4.1 Safety Statements
S16;S25;S36/37/39;S45
4.1 Packing Group
II
4.1 Hazard Class
3
4.1 Hazard Declaration
H225-H314
4.1 RIDADR
UN 2924
4.1 Caution Statement
P210-P280-P305 + P351 + P338-P310
4.1 WGK Germany
3
4.1 Sensitive
Moisture & Light Sensitive
4.2 Specification

The Trimethyliodosilane, with the CAS register number 16029-98-4, has other names as iodotrimethylsilane; iodotrimethylsilyl iodide; tmis; ct3610;iodotrimethyl-silan; silane, iodotrimethyl-; trimethyliodosilane(tmis); trimethyliodosilane.

The characteristics of this chemical could be summarized as: (1)ACD/LogP: 2.83; (2)ACD/LogD(pH5.5): 2.83; (3)ACD/LogD(pH7.4): 2.83; (4)ACD/BCF(pH5.5): 83.47; (5)ACD/BCF(pH7.4): 83.47; (6)ACD/KOC(pH5.5): 826.1; (7)ACD/KOC(pH7.4): 826.1; (8)IndexofRefraction: 1.479; (9)MolarRefractivity: 37.63cm3; (10)MolarVolume: 132.6cm3; (11)Polarizability: 14.91×10-24 cm3; (12)SurfaceTension: 21.2dyne/cm; (13)Density: 1.508g/cm3; (14)FlashPoint: 15.2°C; (15)EnthalpyofVaporization: 32.66kJ/mol; (16)BoilingPoint: 101.5°Cat760mmHg; (17)VapourPressure: 40.5mmHgat25°C.

This is a kind of flammable liquid and is sensitive to light and moisture, so it should be kept with the storage temp. of -20°C. Being among the highly flammable chemicals, it may catch fire in contact with air, only needing brief contact with an ignition source, and it has a very low flash point or evolve highly flammable gases in contact with water. Besides, it is corrosive for it may destroy living tissue on contact. What's more, it may reacts violently with water and then causes burns.

As for so many dangerous possibilities, you should be very careful while dealing with this chemical. First, wear suitable protective clothing, gloves and eye/face protection and then keep away from sources of ignition - No smoking. But if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; If in case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water); And if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Except all these, remember to avoid contacting with eyes, for it is very irritant to our eyes. And you could also go to WGK Germany? 3 to obtain more safety information.

As for its product categories, there are various, including silane compounds; si (classes of silicon compounds); silicon compounds (for synthesis); si-x (f, br, i) compounds; synthetic organic chemistry; alkyl silanes; blocking agents; protective agents; silylating agents, while its preparation products are including 1-fluoro-4-(trifluoromethylthio)benzene, 4-fluorothiophenol, eschenmoser's salt, (2s)-2-amino-3-(5-bromo-1h-indol-3-yl)propanoic acid, 5-methyl-l-tryptophan. Besides, its raw materials are the aluminium and hexamethyldisiloxane.

When comes to its usage, we should say it is widely used in many ways, such as the organic synthesis and other synthsis of medicines. And you could also get this kind of chemical by the below method.

Firstly, react 5.6g(0.21mol) aluminite powder and 16.2g (0.10mol) HMDSO in the reactor and then replace the air with nitrogen; Secondly, heat to 60℃, add 50.8g(0.2mol) iodine while stiring and then
heat up to 140℃ and have the backflow for 1.5h; Thirdly, go through the atmospheric distillation and finally you could get 32.6-35.3g TMSI, with the productivity of 82-88%.

Additionally, you could convert the following data information into the molecular structure:
SMILES:I[Si](C)(C)C
InChI:InChI=1/C3H9ISi/c1-5(2,3)4/h1-3H3
InChIKey:CSRZQMIRAZTJOY-UHFFFAOYAB

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H225 Highly flammable liquid and vapour

H314 Causes severe skin burns and eye damage

Precautionary statement(s)
Prevention

P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.

P233 Keep container tightly closed.

P240 Ground and bond container and receiving equipment.

P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment.

P242 Use non-sparking tools.

P243 Take action to prevent static discharges.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P264 Wash ... thoroughly after handling.

Response

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P370+P378 In case of fire: Use ... to extinguish.

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 BRN
1731136
9.1 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.
9.2 Chemical Properties
Straw liquid
9.3 Uses
An efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage
9.4 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.
9.5 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.]
9.6 Usage
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.
10. Computational chemical data
  • Molecular Weight: 200.094g/mol
  • Molecular Formula: C3H9ISi
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 199.95182
  • Monoisotopic Mass: 199.95182
  • Complexity: 28.4
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Topological Polar Surface Area: 0
  • Heavy Atom Count: 5
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccBAAAgAAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAEBAAAAAAAAAAAABCAAAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
11. Question & Answer
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