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449458 Sigma-Aldrich

(tert-Butyldimethylsilyloxy)acetaldehyde

90%

  • CAS Number 102191-92-4

  • Linear Formula (CH3)3CSi(CH3)2OCH2CHO

  • Molecular Weight 174.31

  •  MDL number MFCD01321229

  •  PubChem Substance ID 24868481

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Building Blocks, C8, Carbonyl Compounds, Chemical Synthesis,
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.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
UN 1989C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
140.0 °F - closed cup
Flash Point(C) 
60 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles
Peer-Reviewed Papers
15

References

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