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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

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

523380-BULK:
523380-5G:
523380-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC3902V
BGBC3097V
BGBC2196V
BGBB8895
BGBB6134V

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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)
Linear porphyrin dimers with fluorenyl arms linked by an ethynyl bridge.
Merhi A, et al.
Tetrahedron, 69(34), 7112-7124 (2013)
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)
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)
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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