4-[(Trimethylsilyl)ethynyl]benzaldehyde

Base Information

• Chemical Name: 4-[(Trimethylsilyl)ethynyl]benzaldehyde
• CAS No.: 77123-57-0
• Molecular Formula: C12H14OSi
• Molecular Weight: 202.328
• Hs Code.: 2931900090
• European Community (EC) Number: 878-916-2
• DSSTox Substance ID: DTXSID90377990
• Nikkaji Number: J1.067.536G
• Wikidata: Q72514463
• Mol file: 77123-57-0.mol

Synonyms:77123-57-0;4-[(Trimethylsilyl)ethynyl]benzaldehyde;4-(Trimethylsilyl)ethynylbenzaldehyde;4-((Trimethylsilyl)ethynyl)benzaldehyde;4-(2-trimethylsilylethynyl)benzaldehyde;4-[2-(trimethylsilyl)ethynyl]benzaldehyde;4-(trimethylsilylethynyl)benzaldehyde;MFCD02093765;4-(2-(trimethylsilyl)ethynyl)benzaldehyde;Benzaldehyde, 4-[(trimethylsilyl)ethynyl]-;SCHEMBL701214;DTXSID90377990;p-trimethylsilylethynylbenzaldehyde;4-trimethylsilylethynylbenzaldehyde;UZQDUXAJFTWMDT-UHFFFAOYSA-N;4-trimethylsilylethynyl benzaldehyde;BCP18367;AB7791;BBL103651;STL557461;4-trimethylsilanylethynyl-benzaldehyde;4-(trime-thylsilylethynyl)benzaldehyde;AKOS005175105;DS-7065;2-ethynyl-4-(trimethylsilyl)benzaldehyde;SY081454;CS-0126636;FT-0649138;T3827;4-[(Trimethylsilyl)ethynyl]benzaldehyde, 97%;A19157;4-(2-(TRIMETHYLSILYL)ETHYNYL) BENZALDEHYDE;Isopropyl3-oxo-2,3-dihydrospiro[indene-1,4-piperidine]-1-carboxylate

Chemical Property of 4-[(Trimethylsilyl)ethynyl]benzaldehyde

Chemical Property:

• Vapor Pressure: 0.0111mmHg at 25°C
• Melting Point: 66-70 °C(lit.)
• Refractive Index: 1.514
• Boiling Point: 262.1 °C at 760 mmHg
• Flash Point: 112.3 °C
• PSA: 17.07000
• Density: 0.98 g/cm³
• LogP: 2.72800
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 202.081391600
• Heavy Atom Count: 14
• Complexity: 255

Purity/Quality:

98%, ^*data from raw suppliers

4-?(Trimethylsilyl)?ethynylbenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)C#CC1=CC=C(C=C1)C=O
• Uses: 4-?(Trimethylsilyl)?ethynylbenzaldehyde is a useful reactant for the synthesis of acetylene-?substituted naphthalene diimides in polar solvents.

Technology Process of 4-[(Trimethylsilyl)ethynyl]benzaldehyde

There total 14 articles about 4-[(Trimethylsilyl)ethynyl]benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-bromo-benzaldehyde (1122-91-4) + trimethylsilylacetylene (1066-54-2) → 4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0)

Guidance literature:

With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/adsc.200606135

Reference yield: 99.0%

4-bromo-benzaldehyde (1122-91-4) + trimethylsilylacetylene (1066-54-2) → 1,4-bis(trimethylsilyl)-1,3-butadiyne (4526-07-2) + 4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 25 ℃; Yields of byproduct given;

DOI:10.1021/jo9808021

Reference yield: 99.0%

4-trimethylsilylethynylbenzaldehyde ethylene acetal (193903-54-7) → 4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0)

Guidance literature:

With trifluoroacetic acid; In water; at 25 ℃; for 10h;

DOI:10.1039/c9cc06916j

upstream raw materials:

4-bromo-benzaldehyde

trimethylsilylacetylene

N,N-dimethyl-formamide

p-(iodophenyl)carboxaldehyde

Downstream raw materials:

meso-<4-(trimethylsilylethynyl)phenyl>dipyrromethane

Refernces

• 1、 Huang, Hao,Li, Fumin,Zhang, Ying,Chen. "Two-dimensional graphdiyne analogue Co-coordinated porphyrin covalent organic framework nanosheets as a stable electrocatalyst for the oxygen evolution reaction". . p. 5575 - 5582. Retrieved 2019.
• 2、 Eisterhold, Andrew M.,Puangsamlee, Thamon,Otterbach, Steffen,Br?se, Stefan,Weis, Patrick,Wang, Xiqu,Kutonova, Ksenia V.,Miljani?, Ognjen ?.. "Expanded Cyclotetrabenzoins". supporting information. p. 781 - 785. Retrieved 2021/01/26.
• 3、 Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel. "α-Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1-(Dialkylamino)-1,2,3-triazoles". supporting information. p. 6943 - 6948. Retrieved 2021/02/26.