2-(trimethylsilyl)ethan-1-ol

• ChemBase ID: 22413
• Molecular Formular: C5H14OSi
• Molecular Mass: 118.24956
• Monoisotopic Mass: 118.0813916
• SMILES: C[Si](C)(C)CCO
• Canonical SMILES: OCC[Si](C)(C)C
• InChI: InChI=1S/C5H14OSi/c1-7(2,3)5-4-6/h6H,4-5H2,1-3H3
• InChIKey: ZNGINKJHQQQORD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(trimethylsilyl)ethan-1-ol
• IUPAC Traditional name: 2-(trimethylsilyl)ethanol
• Synonyms: 2-(Trimethylsilyl)ethanol; 2-Trimethylsilylethanol; (2-Hydroxyethyl)trimethylsilane; 2-(Trimethylsilyl)ethan-1-ol; 2-(Trimethylsilyl) ethanol; 2-Hydroxyethyltrimethylsilane; 2-(Trimethylsilyl)ethanol; (2-羟基乙基)三甲基硅烷; 2-(三甲基硅基)乙醇

Database IDs

• CAS Number: 2916-68-9
• EC Number: 220-844-5
• MDL Number: MFCD00002825
• Beilstein Number: 1732034
• PubChem SID: 160985720; 24853596; 24889708
• PubChem CID: 18013

CALCULATED PROPERTIES

• Acid pKa: 15.533852
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.2768
• LogD (pH = 7.4): 1.2768
• Log P: 1.2768
• Molar Refractivity: 28.6919 cm^3
• Polarizability: 13.48985 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 71-72°C/10mm; 71-72°C/10mm; 71-73 °C/35 mmHg(lit.); 71-73°C
• Flash Point: 132.8 °F; 50°C(122°F); 56 °C; 56°C
• Density: 0.825; 0.825 g/mL at 25 °C(lit.)
• Refractive Index: 1.4250; n20/D 1.423; n20/D 1.423(lit.)
• Hydrophobicity(logP): 1.386

Safety Information

• Storage Warning: FLAMMABLE; Flammable/Irritant/Light Sensitive/Moisture Sensitive/Keep Cold/Store under Argon
• RTECS: KM5480000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1987; UN1987
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10; 10-36/37/38
• Safety Statements: 16; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1987 3/PG 3

Product Information

• Purity: ≥98.0% (GC); 95%; 97%; 98%; 98+%; 99%
• Grade: purum
• Linear Formula: (CH3)3SiCH2CH2OH

DETAILS

Sigma Aldrich - 226890

Application
Protecting reagent for carboxyl1 and phosphate2,3,4 groups.
Used to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates.
Packaging
1, 10, 50 g in glass bottle

Sigma Aldrich - 92747

Other Notes
Component for protecting groups cleavable with fluoride ion1,2,3; Anomeric protection of carbohydrates4,5

REFERENCES

• Carboxyl groups can be protected as 2-(trimethylsilyl)ethyl (TMSE) esters by carbodiimide coupling: Helv. Chim. Acta, 60, 2711 (1977); J. Org. Chem., 62, 93 (1997), from the acid chloride in pyridine: Helv. Chim. Acta, 60, 3039 (1977), or refluxing the acid in THF in the presence of TMS chloride: J. Am. Chem. Soc., 106, 3030 (1984). The TMSE protecting group is useful in peptide synthesis. Cleavage is readily effected with TBAF in DMF or DMSO: Helv. Chim. Acta, 60, 2711 (1977); Bioorg. Med. Chem. Lett., 3, 437 (1993).