449458

(tert-Butyldimethylsilyloxy)acetaldehyde

90%

• Synonym(s): (tert-Butyldimethylsiloxy)acetaldehyde, 2-(tert-Butyldimethylsilyloxy)acetaldehyde, 2-[(tert-Butyl)dimethylsiloxy]acetaldehyde, 2-[(tert-Butyldimethylsilanyl)oxy]acetaldehyde, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]acetaldehyde, Dimethyl-tert-butylsilyloxyacetaldehyde
• Linear Formula: (CH₃)₃CSi(CH₃)₂OCH₂CHO
• CAS Number: 102191-92-4
• Molecular Weight: 174.31
• MDL number: MFCD01321229
• UNSPSC Code: 12352100
• PubChem Substance ID: 24868481
• NACRES: NA.22

Properties

• Assay: 90%
• refractive index: n20/D 1.432 (lit.)
• bp: 165-167 °C (lit.)
• density: 0.915 g/mL at 25 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: CC(C)(C)[Si](C)(C)OCC=O
• InChI: 1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3
• InChI key: MEBFFOKESLAUSJ-UHFFFAOYSA-N

Description

Application

(tert-Butyldimethylsilyloxy)acetaldehyde is a versatile reagent commonly used in synthetic glycobiology. It can act both as an aldol donor and an aldol acceptor in the stereocontrolled production of erythrose. It is used as an important reagent in the total synthesis of (+)-ambruticin, (−)-laulimalide, (−)-salinosporamide A, and (+)-leucascandrolide A.

Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Warning
• Hazard Statements: H226 - H315 - H319 - H335
• Precautionary Statements: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 140.0 °F - closed cup
• Flash Point(C): 60 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves