chlorotriethylsilane

• ChemBase ID: 88299
• Molecular Formular: C6H15ClSi
• Molecular Mass: 150.7218
• Monoisotopic Mass: 150.06315469
• SMILES: [Si](CC)(CC)(CC)Cl
• Canonical SMILES: CC[Si](CC)(CC)Cl
• InChI: InChI=1S/C6H15ClSi/c1-4-8(7,5-2)6-3/h4-6H2,1-3H3
• InChIKey: DCFKHNIGBAHNSS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorotriethylsilane
• IUPAC Traditional name: chlorotriethylsilane
• Synonyms: Chlorotriethylsilane solution; TESCl; Triethylchlorosilane; Chlorotriethylsilane; TRIETHYLCHLOROSILANE; Triethylsilyl chloride; Chlorotriethylsilane; Silane E3; 三乙基氯硅烷 溶液; 三乙基氯硅烷; 硅烷 E3

Database IDs

• CAS Number: 994-30-9
• EC Number: 213-615-6
• MDL Number: MFCD00000507
• Beilstein Number: 1732860
• PubChem SID: 24886910; 24854077; 162075275; 24889361; 24863184
• PubChem CID: 13819

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.9347
• LogD (pH = 7.4): 2.9347
• Log P: 2.9347
• Molar Refractivity: 37.639 cm^3
• Polarizability: 16.519722 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -75°C; ca -75°C
• Boiling Point: 142-144 °C(lit.); 142-147°C; 145-147°C
• Flash Point: 1.4 °F; -17 °C; 29°C(84°F); 30 °C; 30°C; 86 °F
• Density: 0.886 g/mL at 25 °C; 0.898; 0.898 g/mL at 25 °C(lit.); 0.899
• Refractive Index: 1.4310; n20/D 1.43(lit.)
• Hydrophobicity(logP): 2.195

Safety Information

• Storage Warning: Corrosive/Flammable/Toxic/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 2924; 2986; UN2986
• German water hazard class: 1
• Hazard Class: 3; 8
• Packing Group: 2; II
• Risk Statements: 10-14-22-35; 11-14-19-35-37
• Safety Statements: 16-26-36/37/39-43-45; 16-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H314-H335; H226-H301-H314; H301-H314-H318-H226
• GHS Precautionary statements: P210-P261-P280-P305 + P351 + P338-P310; P280-P301 + P310-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310-P403
• 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; UN 2986 8/PG 2
• Supplemental Hazard Statements: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.

Product Information

• Purity: ≥97.0% (GC); ≥99.0%; 95%; 97%; 98+%; 99%
• Concentration: 1.0 M in THF
• Grade: for GC derivatization; produced by Wacker
• Linear Formula: (C2H5)3SiCl

DETAILS

MP Biomedicals - 05221548

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 372943

Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 235067

Application
Employed together with Grignard reagents in a palladium-catalyzed carbosilylation of allenes. The Grignard attacks the allene central carbon and the terminal carbon is silylated.1
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 75986

Other Notes
prices for bulk quantities on request
Packaging
5 kg in ss drum

Sigma Aldrich - 90383

Other Notes
Silylating agent with some advantage over the trimethylsilylating agents for synthetic and analytical applications1,2,3

Toronto Research Chemicals - C421750

Chlorotriethylsilane is used in the preparation of potent silylating agent and lewis acid catalyst. Chlorotriethylsilane derivatived ethers have been shown to be more stable towards hydrolysis than are trimethyl ethers.

REFERENCES

• Alvisi, C. et al.: J. Org. Chem., 63, 1330 (1998): Higashiya, S. et al.: J. Org. Chem., 69, 6326 (2004)
• Hicks, J.D. et al.: Org. Lett., 9, 5621 (2004)
• Silylation reagent (see Appendix 4). Generally, triethylsilyl (TES) ethers are 10-100x more stable to hydrolysis than their TMS (see Chlorotrimethylsilane, A13651) counterparts but much less so than TBDMS (see tert-Butyldimethylchlorosilane, A13064): J. Org. Chem., 48, 1970 (1983).
• Silylation of alcohols in the presence of e.g. pyridine: J. Chem. Soc., Chem. Commun., 156 (1979); imidazole-DMF: Helv. Chim. Acta, 64, 2002 (1981); or catalyzed by DMAP: J. Org. Chem., 52, 598 (1987) have been reported. The TES group is readily cleaved with TBAF or other F^- reagents. Catalytic amounts of FeCl₃ in MeOH has also been recommended: Synlett, 1260 (2006). Selective cleavage in the presence of TBDMS has been achieved with aqueous AcOH in THF: Liebigs Ann. Chem., 1281 (1986), or 2% HF in acetonirile: Tetrahedron Lett., 26, 5239 (1985).