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523380 Sigma-Aldrich

4-[(Trimethylsilyl)ethynyl]benzaldehyde

97%

  • CAS Number 77123-57-0

  • Linear Formula (CH3)3SiC≡CC6H4CHO

  • Molecular Weight 202.32

  •  MDL number MFCD02093765

  •  PubChem Substance ID 24874332

  •  NACRES NA.22

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Properties

Related Categories Aldehydes, Building Blocks, C10-C12, Carbonyl Compounds, Chemical Synthesis,
assay   97%
mp   66-70 °C (lit.)
storage temp.   room temp
SMILES string   C[Si](C)(C)C#Cc1ccc(C=O)cc1
InChI   1S/C12H14OSi/c1-14(2,3)9-8-11-4-6-12(10-13)7-5-11/h4-7,10H,1-3H3
InChI key   UZQDUXAJFTWMDT-UHFFFAOYSA-N

Description

General description

4-[(Trimethylsilyl)ethynyl]benzaldehyde can be synthesized by reacting 4-bromobenzaldehyde and triphenylphosphine in anhydrous triethylamine with ethynyltrimethylsilane and then with palladium(II) acetate under argon. It can also be prepared by Sonogashira coupling reaction between 4-bromobenzaldehyde and (trimethylsilyl) ethynyl.

Application

4-[(Trimethylsilyl)ethynyl]benzaldehyde may be used in the preparation of the following:
• 4,4,5,5-tetramethyl-2-{4-[(trimethylsilyl)ethynyl]phenyl}imidazolidine-1,3-diol
• 5,10,15-triphenyl-20-{4-[2-(trimethylsilyl)ethynyl]phenyl}porphyrin

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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