2-[(tert-butyldimethylsilyl)oxy]acetaldehyde

• ChemBase ID: 146379
• Molecular Formular: C8H18O2Si
• Molecular Mass: 174.31282
• Monoisotopic Mass: 174.10760635
• SMILES: CC(C)(C)[Si](C)(C)OCC=O
• Canonical SMILES: O=CCO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3
• InChIKey: MEBFFOKESLAUSJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(tert-butyldimethylsilyl)oxy]acetaldehyde
• IUPAC Traditional name: 2-[(tert-butyldimethylsilyl)oxy]acetaldehyde
• Synonyms: (tert-Butyldimethylsilyloxy)acetaldehyde; (叔丁基二甲基硅氧基)乙醛

Database IDs

• CAS Number: 102191-92-4
• MDL Number: MFCD01321229
• PubChem SID: 24868481; 162240577
• PubChem CID: 4187788

CALCULATED PROPERTIES

• Acid pKa: 16.031727
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4282
• LogD (pH = 7.4): 1.4282
• Log P: 1.4282
• Molar Refractivity: 43.2686 cm^3
• Polarizability: 19.165934 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 165-167 °C(lit.)
• Flash Point: 140 °F; 60 °C
• Density: 0.915 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.432(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 1989
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1989 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 90%
• Linear Formula: (CH3)3CSi(CH3)2OCH2CHO

DETAILS

Sigma Aldrich - 449458

Application
Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (-)-dactylodide.1
This acetaldehyde yields addition products in good yields and ee′s in various total syntheses of biologically active molecules1
Packaging
1, 5 g in glass bottle