523380
4-[(Trimethylsilyl)ethynyl]benzaldehyde
97%
Sinónimos:
4-(Trimethylsilylethynyl)benzaldehyde, 4-[2-(Trimethylsilyl)ethynyl]benzaldehyde, p-[(Trimethylsilyl)ethynyl]benzaldehyde
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About This Item
Fórmula lineal:
(CH3)3SiC≡CC6H4CHO
Número de CAS:
Peso molecular:
202.32
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
97%
mp
66-70 °C (lit.)
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
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
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Cascade Reactions of Me3Si-Substituted Imidazolidine-1, 3-Diols with PbO2, Including Oxidation of the Corresponding Diol and Subsequent Elimination of the Trimethylsilyl Fragment.
Tretyakov E, et al.
European Journal of Organic Chemistry, 2007(22), 3639-3647 (2007)
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