176910-67-1

Basic information

• Product Name: Benzaldehyde, 2-[(4-Methoxyphenyl)ethynyl]-
• Synonyms: Benzaldehyde, 2-[(4-Methoxyphenyl)ethynyl]-;2-[2-(4-methoxyphenyl)ethynyl]- benzaldehyde
• CAS NO: 176910-67-1
• Molecular Formula: C₁₆H₁₂O₂
• Molecular Weight: 236.26528
• EINECS: -0
• Mol File: 176910-67-1.mol
• Article Data: 80

Chemical Properties

• Melting Point: 46-47 °C
• Boiling Point: 404.0±30.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Benzaldehyde, 2-[(4-Methoxyphenyl)ethynyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2-[(4-Methoxyphenyl)ethynyl]-(176910-67-1)
• EPA Substance Registry System: Benzaldehyde, 2-[(4-Methoxyphenyl)ethynyl]-(176910-67-1)

Safety Data

• Hazardous Substances Data: 176910-67-1(Hazardous Substances Data)

Usage

General Description

Benzaldehyde, 2-[(4-methoxyphenyl)ethynyl]- is a chemical compound that belongs to the class of aromatic aldehydes. It is composed of a benzene ring with an aldehyde functional group and a phenyl group attached to a carbon atom by a triple bond. The 4-methoxyphenyl group attached to the alkyne carbon provides the compound with its distinct properties. This chemical is commonly used in the synthesis of organic compounds and pharmaceuticals and also has applications in the flavor and fragrance industry due to its characteristic almond-like odor. Additionally, it is used in the production of dyes and pesticides.

Upstream product

• 38846-64-9 2-ethynylbenzaldehyde 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 696-62-8 para-iodoanisole 
• 26260-02-6 2-iodobenzaldehyde 
• 768-60-5 4-methoxyphenylacetylen 
• 123-11-5 4-methoxy-benzaldehyde 
• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 5159-41-1 2-iodobenzyl alcohol 
• 405198-79-0 {2-[2-(4-methoxyphenyl)ethynyl]phenyl}methanol 

Downstream Products

• 391611-15-7 tert-Butyl-[1-[2-(4-methoxy-phenylethynyl)-phenyl]-meth-(E)-ylidene]-amine 
• 1155382-45-8 C₁₉H₂₀O₃ 
• 1229244-32-9 3-(3-(4-methoxyphenyl)-1H-isochromen-1-yl)-1H-indole 
• 1229244-51-2 (5H-benzo[b]carbazol-6-yl)(4-methoxyphenyl)methanone 
• 1244036-12-1 (4-methoxyphenyl)(2-p-tolylnaphthalen-1-yl)methanone 
• 1239320-77-4 tert-butyl 6-(4-methoxyphenyl)indolo[2,1-a]isoquinoline-12-carboxylate 
• 1256498-47-1 1-((4-methoxyphenyl)ethynyl)-2-(2-methylprop-1-en-1-yl)benzene 
• 1185881-61-1 3'-(4-methoxyphenyl)-2,2-dimethyl-3',4'-dihydro-1'H-spiro[[1,3]dioxane-5,2'-naphthalene]-4,6-dione 
• 1185881-68-8 dimethyl 3-(4-methoxyphenyl)-3,4-dihydronaphthalene-2,2(1H)-dicarboxylate 
• 1185881-52-0 5-(2-(4-methoxyphenethyl)benzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1185881-57-5 dimethyl 2-(2-(4-methoxyphenethyl)benzylidene)malonate 
• 1370697-49-6 2-(4-chlorophenyl)-1,3-diiodonaphthalene 
• 6938-39-2 n-propyl 4-methoxybenzoate 
• 1370697-25-8 3-(4-chlorophenyl)-1-(2-((4-methoxyphenyl)ethynyl)phenyl)prop-2-yn-1-ol 

Relevant articles and documents

B(C6F5)3: A lewis acid that brings the light to the solid state

The straightforward coordination of the Lewis acid B(C6F5)3 to classical, non-emitting aldehydes results in solid-state photoluminescence. Variation of the electronic properties of the carbonyl moieties lead to the modulation of the solid-state emission colors, covering the entire visible spectrum with quantum yields up to 0.64. Steady-state spectroscopy in combination with X-ray diffraction analysis and DFT calculations confirm that intermolecular interactions between the Lewis adducts are responsible for the observed luminescence. Alteration of the latter interactions induces, moreover, remarkable solid-state phenomena such as piezochromism. The versatility and simplicity of our approach facilitate the future development of solid-state emitting materials. Turn on the light: A straightforward methodology can be used to "switch on" the solid-state fluorescence of non-emitting carbonyl compounds. Subtle electronic changes in the aldehyde moieties lead to a variety of emission colors that cover the entire visible spectrum. The materials also display pressure-dependent luminescent properties (piezochromism).

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

Synthesis of N-(isoquinolin-1-yl)sulfonamides via Ag2O-catalyzed tandem reaction of ortho-alkynylbenzaldoximes with benchtop stabilized ketenimines

In this project, a moderately efficient approach to multisubstituted N-(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing ortho-alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of Ag2O, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline N-oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.