iodotrimethylsilane

• ChemBase ID: 77997
• Molecular Formular: C3H9ISi
• Molecular Mass: 200.09353
• Monoisotopic Mass: 199.95182482
• SMILES: [Si](C)(C)(C)I
• Canonical SMILES: C[Si](I)(C)C
• InChI: InChI=1S/C3H9ISi/c1-5(2,3)4/h1-3H3
• InChIKey: CSRZQMIRAZTJOY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: iodotrimethylsilane
• IUPAC Traditional name: iodotrimethylsilane; trimethylsilyl iodide
• Synonyms: TMIS; Trimethyliodosilane; Iodotrimethylsilane; Iodotrimethylsilane; Trimethylsilyl iodide; TRIMETHYLIODOSILANE; Trimethylsilyl iodide; TMS iodide; 碘代三甲硅烷; 三甲基碘硅烷

Database IDs

• CAS Number: 16029-98-4
• EC Number: 240-171-0
• MDL Number: MFCD00001028
• Beilstein Number: 1731136
• PubChem SID: 24851696; 24881036; 162042833
• PubChem CID: 85247
• Chemspider ID: 76879
• Wikipedia Title: Trimethylsilyl_iodide

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3119
• LogD (pH = 7.4): 2.3119
• Log P: 2.3119
• Molar Refractivity: 30.6811 cm^3
• Polarizability: 14.281235 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 105-106°C; 106 °C(lit.); 106°C/760mm
• Flash Point: -2°C(28°F); -24 °F; -31 °C; -31°C
• Density: 1.406 g/mL at 25 °C(lit.); 1.41 g/ml; 1.440
• Refractive Index: 1.4760; n20/D 1.471(lit.)

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen
• Storage Warning: Flammable/Corrosive/Hygroscopic/Store under Argon/Store at -20°C; Moisture & Light Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-14-34
• Safety Statements: 16-26-36/37/39-43.11-45; 16-26-36/37/39-43-45; 8-9-16-23-26-36/37/39-45-60
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: -20°C

Product Information

• Purity: ≥90%; ≥98.0% (AT); 97%; 97%, stab. with copper
• Grade: purum
• Contains: ~1% copper as stabilizer; copper as stabilizer
• Shipped in: wet ice
• Linear Formula: (CH3)3SiI

DETAILS

MP Biomedicals - 02157076

Purity: >90%
Stabilized with copper
1 ml = approx. 1.41 g

Sigma Aldrich - 195529

Application
Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.1
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.
Packaging
5, 25, 100 g in ampule

Sigma Aldrich - 58118

Other Notes
Versatile reagent, e.g. for the cleavage of ethers, esters, carbamates and ketals, for the deoxygenation of sulfoxides, for the synthesis of iodides, etc. Reviews1,2,3; Powerful silylating agent4,5

REFERENCES

• Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).
• Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).
• Reactive silylating agent for conversion of ketones to silyl enol ethers (see Appendix 4). In triethylamine, the rate of silyl enol ether formation by TMS iodide is 7x10⁹ times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980). In combination with Hexamethyldisilazane, A15139, unsymmetrical ketones give the thermodynamically more stable isomer: Synthesis, 730 (1979).
• Alcohols are converted to alkyl iodides: Tetrahedron Lett., 2659 (1977). ɑɑ-Diaryl alcohols are reduced to the corresponding alkanes: Tetrahedron, 51, 11043 (1995); Synth. Commun., 26, 101 (1996).
• Effective reagent for the O-alkyl cleavage of carboxylic esters: J. Am. Chem. Soc., 99, 968 (1977). The reaction can be catalyzed by iodine: J. Org. Chem., 44, 2185 (1979).
• Alkyl carbamates are cleaved to amines, via the TMS esters: J. Chem. Soc., Chem. Commun., 315 (1978); for application to cleavage of N-Cbz and N-Boc groups, see: J. Chem. Soc., Chem. Commun., 495 (1979).
• Catalyst for the protection of alcohols, under mild neutral conditions, as MOM ethers by trans-acetalization with Dimethoxymethane, A12055: Synthesis, 896 (1983), and as THP ethers by acetalization with dihydropyran: Synthesis, 703 (1985).
• Catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives, effective at lower temperatures than bromotrimethylsilane: Org. Lett., 5, 1661 (2003).
• For reviews of the use of iodotrimethylsilane in organic synthesis, see: Synthesis, 861 (1980); Tetrahedron, 38, 2225 (1982); Adv. Silicon Chem., 1, 1 (1991).