2579-22-8

Basic information

• Product Name: Phenylpropiolaldehyde
• Synonyms: 2-Propynal, 3-phenyl-;3-Phenylpropynal;Benzenepropiolaldehyde;Phenylacetylenecarboxaldehyde;Phenylpropynal;Propiolaldehyde, phenyl-;PHENYLPROPARGYL ALDEHYDE;PHENYLPROPIOLALDEHYDE
• CAS NO: 2579-22-8
• Molecular Formula: C₉H₇N₃O
• Molecular Weight: 130.14
• EINECS: 219-942-0
• Product Categories: Aldehydes;Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 2579-22-8.mol

Chemical Properties

• Melting Point: 139-140 °C (decomp)
• Boiling Point: 118 °C13 mm Hg(lit.)
• Flash Point: 202 °F
• Appearance: /
• Density: 1.064 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0428mmHg at 25°C
• Refractive Index: n20/D 1.604(lit.)
• Storage Temp.: 2-8°C
• BRN: 1099281
• CAS DataBase Reference: Phenylpropiolaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylpropiolaldehyde(2579-22-8)
• EPA Substance Registry System: Phenylpropiolaldehyde(2579-22-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 9-19
• Hazardous Substances Data: 2579-22-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Phenylpropiolaldehyde is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs and enhance the properties of existing ones.
Used in Fragrance Industry:
It serves as a key component in the creation of fragrances, leveraging its strong and distinctive odor to contribute to the unique scents of perfumes and other scented products.
Used in Chemical Synthesis:
Phenylpropiolaldehyde is utilized as a reagent in organic synthesis, playing a crucial role in the production of a wide range of chemical compounds.
Used in Food Industry:
It is employed as a flavoring agent, adding unique taste and aroma profiles to various food products, enhancing their overall sensory appeal.
However, due to its potential health and environmental risks, Phenylpropiolaldehyde is considered a hazardous substance and should be handled with care to mitigate any associated risks.

InChI:InChI=1/C9H6O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,8H

Upstream product

• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 536-74-3 phenylacetylene 
• 64-17-5 ethanol 
• 1004-22-4 (phenylethynyl)sodium 
• 109-94-4 formic acid ethyl ester 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 84452-21-1 2-hydroxy-4-phenyl-3-butynenitrile 
• 622-76-4 1-phenyl-1-butyne 
• 93-61-8 N-methyl-N-phenylformamide 
• 10025-87-3 trichlorophosphate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 32569-87-2 4-methoxyl-phenylacetylene 
• 923026-40-8 4-phenyl-1-[(3-phenylprop-2-yn-1-yl)oxy]but-3-yn-2-one 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 1071813-66-5 C₁₅H₁₀N₆OS₂ 
• 5807-05-6 3-(morpholin-4-yl)-3-phenyl-2-propenal 
• 18669-44-8 3-phenylpropynal 2,4-dinitrophenylhydrazone 
• 109254-47-9 2-[2]naphthyl-5-phenyl-pent-2-en-4-ynoic acid 
• 16807-58-2 C₂₁H₂₀O₄ 
• 75989-95-6 2-phenyl-4-phenylpropargyliden-2-oxazolin-5-on 
• 139713-00-1 (E)-1-(5-phenyltetrazol-1-yl)-4-phenyl-1-aza-1-buten-3-yne 
• 112403-24-4 phenylethynylbis(dimedonyl)methane 
• 118673-10-2 Allyl-[3-phenyl-prop-2-yn-(E)-ylidene]-amine 
• 169274-92-4 ((4S,5S)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-[3-phenyl-prop-2-yn-(E)-ylidene]-amine 
• 169274-93-5 ((4R,5R)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-[3-phenyl-prop-2-yn-(E)-ylidene]-amine 
• 77889-98-6 (E)-3-phenoxy-3-phenylacrylaldehyde 
• 1006-67-3 5-phenylisoxazole 

Relevant articles and documents

P-Stereogenic Phosphines Directed Copper(I)-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions

A new pair of P-stereogenic ligands with multiple chiral centers were synthesized and used in the copper(I)-catalyzed enatioselective [3 + 2] cycloaddition of iminoesters with alkenes. A variety of highly functionalized pyrrolidines were obtained in excellent yield and enatioselectivity. This is the first example of a pair of P-stereogenic ligands working as pseudoenantiomers to tune the enantio- and diastereoselective 1,3-dipolar cycloaddition, and providing a pair of enantiomerically pure pyrrolidines, respectively.

Repetition of chemistry from a recently retracted paper. A cautionary note

The base-catalyzed condensation reaction between (E)-4-phenylbut-2-enal and phenylpropargyl aldehyde recently reported in the literature to provide formylcyclobutadiene was repeated under the published conditions. The product obtained was identified as (E)-5-phenyl-2-((E)-styryl)pent-2-en-4-ynal rather than the reported 2-phenyl-3-styrylcyclobutadiene-1-carboxaldehyde. The structure assignment is supported by NMR and IR data and a x-ray structure of the crystalline alcohol obtained by Luche reduction.

Copper-catalyzed TEMPO addition to propargyl alcohols for the synthesis of vinylic alkoxyamines

A variety of vinylic alkoxyamines derived from propargyl alcohols and 2, 2, 6,6-tetramethylpiperidine N-oxyl (TEMPO) were synthesized in good yields under copper-catalyzed aerobic conditions. A reaction mechanism was proposed, involving the isomerization of propargyl radicals to allenic radicals, and related mechanistic studies were performed. The kinetic isotope effect on the propargyl C-H bond cleavage (α-deprotonation) reaction was observed (kH/kD = 3.76).

A practical synthesis of phenylpropargyl aldehyde from phenylacetylene and N-formylmorpholine

A synthesis of phenylpropargyl aldehyde is described employing formylation of a phenylacetylenic Grignard reagent with N-formylmorpholine. This method afforded the product in excellent yield.

Highly efficient and mild synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives

Synthesis of variously 5-substituted-4-carbaldehyde-1,2,3-triazole derivatives 2 was accomplished by reacting sodium azide with α,β-acetylenic aldehydes 1 in DMSO at room temperature. Therefore, the reaction remains basic avoiding the generation of the hazardous explosive HN3, resulting in a safe process. This mild and general reaction was instantaneous and was essentially quantitative.

The use of acetylenic aldehydes in Baylis-Hillman reactions: Synthesis of versatile allyl propargyl alcohols

The utility of acetylenic aldehydes in Baylis-Hillman reactions giving allyl propargyl alcohols in moderate to good yields is reported.

Synthesis of 1,3-dioxacyclan-2-yl-substituted 1,2,3-triazoles

A new method for preparing 4-(1,3-dioxacyclan-2-yl)-5-phenyl-1,2,3-triazoles in 30–75% yields has been developed on the basis of azide–alkyne cycloaddition to 2-phenylethinyl-1,3-dioxacyclanes. It has been shown that the best results are achieved when the reaction is carried out at 150–155°C in DMSO.

Ionic liquid [Bmim][AuCl4] encapsulated in ZIF-8 as precursors to synthesize N-decorated Au catalysts for selective aerobic oxidation of alcohols

Here we report a novel approach to synthesize Au NPs immobilized on N-doped carbon materials. In this strategy, an ionic liquid (IL) [Bmim][AuCl4] was selected as the precursor for Au NPs and porous framework of ZIF-8 as the host for the IL. Raman spectroscopy, transmission electron microscopy, N2 physical absorption and Fourier infrared spectra confirmed that the IL was successfully incorporated in the ZIF-8 pores. Followed by a thermal treatment under inert atmosphere, highly dispersed Au NPs were obtained and stabilized by nitrogen species from the carbonization of organic ligand in the metal-organic frameworks (MOFs). The [Bmim][AuCl4]@ZIF-8-6.25percent-T materials exhibited high catalytic activity for the selective aerobic oxidation of alcohols, affording excellent yields (up to >99percent) under atmospheric air and base-free conditions. Catalytic reaction along with catalyst characterization results revealed a strong interaction between Au NPs and N species. TEM, XRD and XPS characterization results further suggested that the N species could not only prevent the Au NPs from aggregation, but also further enhance the reaction activity.

Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride

A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.

Visible Light-Induced Cascade Cyclization of 3-Aminoindazoles, Ynals, and Chalcogens: Access to Chalcogen-Containing Pyrimido[1,2- b]-indazoles

A direct cascade cyclization of 3-aminoindazoles, ynals, and accessible chalcogens facilitated by visible light has been developed. A series of fluoroactive selenium/tellurium-substituted pyrimido[1,2-b]-indazoles were easily accessed in moderate to good yields with a broad scope. Furthermore, we surveyed the spectral properties of selenide pyrimido[1,2-b]-indazoles prepared by this method.