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523380

Sigma-Aldrich

4-[(Trimethylsilyl)ethynyl]benzaldehyde

97%

Synonym(s):

4-(Trimethylsilylethynyl)benzaldehyde, 4-[2-(Trimethylsilyl)ethynyl]benzaldehyde, p-[(Trimethylsilyl)ethynyl]benzaldehyde

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About This Item

Linear Formula:
(CH3)3SiC≡CC6H4CHO
CAS Number:
77123-57-0
Molecular Weight:
202.32
MDL number:
MFCD02093765
UNSPSC Code:
12352100
PubChem Substance ID:
24874332
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Linear porphyrin dimers with fluorenyl arms linked by an ethynyl bridge.
Merhi A, et al.
Tetrahedron, 69(34), 7112-7124 (2013)
On the potential of porphyrin-spiked triarylamine stars for bulk heterojunction solar cells.
Kengthanomma T, et al.
Journal of Material Chemistry A, 1(35), 10524-10531 (2013)
Facile synthesis of ethynylated benzoic acid derivatives and aromatic compounds via ethynyltrimethylsilane.
Austin WB, et al.
The Journal of Organic Chemistry, 46(11), 2280-2286 (1981)
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)
Synthesis of covalently bonded nanostructure from two porphyrin molecular wires leading to a molecular tube.
Ishida T, et al.
Tetrahedron Letters, 47(30), 5265-5268 (2006)

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