4-(Trimethylsilyl)ethynylbenzaldehyde
- CAS No.
- 77123-57-0
- Chemical Name:
- 4-(Trimethylsilyl)ethynylbenzaldehyde
- Synonyms
- DK902;4-[(TriMethylsilyl)ethynyl]benzaldehy;4-(TRIMETHYLSILYL)ETHYNYLBENZALDEHYDE;4-[(trimethylsilyl)ethynyl]bezaldehyde;4-[(Trimethysilyl)-ethynyl]benzaldehyde;4-[2-(triMethylsilyl)ethynyl]benzaldehyde;Benzaldehyde, 4-[(triMethylsilyl)ethynyl]-;4-[(TriMethylsilyl)ethynyl]benzaldehyde 97%;Benzaldehyde, 4-[2-(trimethylsilyl)ethynyl]-;4-((Trimethylsilyl)ethynyl)benzaldehyde - [T55948]
- CBNumber:
- CB9237605
- Molecular Formula:
- C12H14OSi
- Molecular Weight:
- 202.32
- MDL Number:
- MFCD02093765
- MOL File:
- 77123-57-0.mol
- MSDS File:
- SDS
| Product description | Number | Pack Size | Price |
| 4-[(Trimethylsilyl)ethynyl]benzaldehyde 97% | 523380 | 5g | $272 |
| 4-(Trimethylsilylethynyl)benzaldehyde min. 98.0 % | T3827 | 1G | $57 |
| 4-(Trimethylsilylethynyl)benzaldehyde min. 98.0 % | T3827 | 5G | $226 |
| 4-(Trimethylsilyl)ethynylbenzaldehyde >99% | OR01513 | 5g | $21 |
| 4-(Trimethylsilyl)ethynylbenzaldehyde >99% | OR01513 | 25g | $89 |
| Melting point | 66-70 °C(lit.) |
|---|---|
| Boiling point | 262.1±32.0 °C(Predicted) |
| Density | 0.98±0.1 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| Appearance | Light brown to brown Solid |
| InChI | 1S/C12H14OSi/c1-14(2,3)9-8-11-4-6-12(10-13)7-5-11/h4-7,10H,1-3H3 |
| InChIKey | UZQDUXAJFTWMDT-UHFFFAOYSA-N |
| SMILES | C[Si](C)(C)C#Cc1ccc(C=O)cc1 |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| PPE | Eyeshields, Gloves, type N95 (US) | |||||||||
| Hazard Codes | T | |||||||||
| WGK Germany | 3 | |||||||||
| HazardClass | IRRITANT | |||||||||
| HS Code | 2931900090 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| NFPA 704 |
|
4-(Trimethylsilyl)ethynylbenzaldehyde price More Price(52)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 523380 | 4-[(Trimethylsilyl)ethynyl]benzaldehyde 97% | 77123-57-0 | 5g | $272 | 2026-04-30 | Buy |
| TCI Chemical | T3827 | 4-(Trimethylsilylethynyl)benzaldehyde min. 98.0 % | 77123-57-0 | 1G | $57 | 2026-04-30 | Buy |
| TCI Chemical | T3827 | 4-(Trimethylsilylethynyl)benzaldehyde min. 98.0 % | 77123-57-0 | 5G | $226 | 2026-04-30 | Buy |
| Apolloscientific | OR01513 | 4-(Trimethylsilyl)ethynylbenzaldehyde >99% | 77123-57-0 | 5g | $21 | 2026-06-04 | Buy |
| Apolloscientific | OR01513 | 4-(Trimethylsilyl)ethynylbenzaldehyde >99% | 77123-57-0 | 25g | $89 | 2026-06-04 | Buy |
4-(Trimethylsilyl)ethynylbenzaldehyde Chemical Properties,Uses,Production
Uses
4-(Trimethylsilyl)ethynylbenzaldehyde is a useful reactant for the synthesis of acetylene-substituted naphthalene diimides in polar solvents.
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.
Synthesis
1122-91-4
1066-54-2
77123-57-0
To a solution of 4-bromobenzaldehyde (3.70 g, 20.0 mmol), cuprous iodide (CuI, 380 mg, 2.00 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 924 mg, 800 μmol) in tetrahydrofuran (THF, 60 mL) was added triethylamine (Et3N, 11.2 mL, 80.3 mmol) and tris methylsilylacetylene (4.24 mL, 30.0 mmol). The reaction mixture was stirred at room temperature under argon (Ar) protection overnight, followed by filtration and washing of the solid with ethyl acetate (EtOAc, 30 mL). The filtrate and washings were combined and concentrated under reduced pressure, and the residue was purified by fast column chromatography (silica gel, petroleum ether, gradient elution to petroleum ether:EtOAc = 98:2) to afford 4-((trimethylsilyl)ethynyl)benzaldehyde as a light brown solid (4.04 g, 100%). Thin layer chromatography (TLC) Rf value (petroleum ether:EtOAc = 4:1) was 0.87. The melting point was 66-67°C (literature [7] reported a melting point of 70°C). Infrared spectra (IR) νmax/cm-1: 2960, 2899, 2832, 2733, 2159, 1702, 1600, 1563, 1412, 1384, 1303, 1251, 1205, 1165, 862, 842.1H NMR (300 MHz, CDCl3) δ: 0.19 (s, 9H, Si( CH3)3), 7.47 (d, 2H, J = 8.1 Hz, Ph-H), 7.68 (d, 2H, J = 7.8 Hz, Ph-H), 9.87 (s, 1H, CHO).13C NMR (75 MHz, CDCl3) δ: 0.3, 98.8, 103.8, 129.1, 129.3, 132.3, 135.5, 191.0 (four carbon signals overlapped or blurred). Mass spectra (MS, GC-EI): 187.1 ([M-CH3]+, 100%), 202.0 (M+, 8%). The spectral data are in agreement with those reported in the literature [7].
References
[1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 15, p. 2101 - 2113
[2] Beilstein Journal of Organic Chemistry, 2014, vol. 11, p. 37 - 41
[3] PLoS ONE, 2015, vol. 10, # 6,
[4] Chemistry - A European Journal, 2010, vol. 16, # 25, p. 7389 - 7394
[5] Chemical Communications, 2011, vol. 47, # 4, p. 1282 - 1284
4-(Trimethylsilyl)ethynylbenzaldehyde Preparation Products And Raw materials
Raw materials
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Preparation Products
4-(Trimethylsilyl)ethynylbenzaldehyde Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
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View Lastest Price from 4-(Trimethylsilyl)ethynylbenzaldehyde manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2019-12-20 | 4-(Trimethylsilyl)ethynylbenzaldehyde
77123-57-0
|
$1.00 | 100g | 99% | Career Henan Chemical Co | ||
 |
2019-12-20 | 4-(Trimethylsilyl)ethynylbenzaldehyde
77123-57-0
|
$1.00 | 100g | 99% | Career Henan Chemical Co |
-
- 4-(Trimethylsilyl)ethynylbenzaldehyde
77123-57-0
- $1.00
- 99%
- Career Henan Chemical Co
-
- 4-(Trimethylsilyl)ethynylbenzaldehyde
77123-57-0
- $1.00
- 99%
- Career Henan Chemical Co
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