6142-95-6

Basic information

• Product Name: PHENYLPROPIOLALDEHYDE DIETHYL ACETAL
• Synonyms: (3,3-Diethoxy-1-propynyl)benzene;3-Phenylpropynal diethyl acetal;Propiolaldehyde, phenyl-, diethyl acetal;PHENYLPROPIOLALDEHYDE DIETHYL ACETAL;PHENYLPROPIOLIC ALDEHYDE DIETHYLACETAL;PHENYLPROPARGYL ALDEHYDE DIETHYL ACETAL;3-PHENYL-2-PROPYNYL ALDEHYDE DIETHYL ACETAL;(3,3-DIETHOXYPROP-1-YN-1-YL)BENZENE
• CAS NO: 6142-95-6
• Molecular Formula: C13H16O2
• Molecular Weight: 204.26
• EINECS: 228-143-6
• Product Categories: Acetals/Ketals/Ortho Esters;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 6142-95-6.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 99-100 °C2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.991 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00922mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• Storage Temp.: 0-6°C
• BRN: 2049715
• CAS DataBase Reference: PHENYLPROPIOLALDEHYDE DIETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLPROPIOLALDEHYDE DIETHYL ACETAL(6142-95-6)
• EPA Substance Registry System: PHENYLPROPIOLALDEHYDE DIETHYL ACETAL(6142-95-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 6142-95-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Preparation

To a flask equipped with a 12-in. Vigreux column and distillation head is added 74.0 gm (0.50 mole) of triethyl orthoformate, 51.0 gm (0.50 mole)of phenylacetylene, and 3.0 gm of zinc iodide* catalyst. The flask must first be heated to 135°C before ethanol starts to reflux. The ethanol distillate (26.4 gm) boiling at 65°-88°C is removed over a period of 1 hr while the temperature of the reaction mixture is raised to 200°-210°C. The reaction mixture is cooled and filtered, the precipitate washed with 5 ml of ether and the ether combined with the filtrate is distilled to afford 73-80 gm (72-78%), b.p. 99-100°C (2.0 mm Hg). The IR spectrum showed absorption at 4.5-μ (—C=C—) and 9.0-μ region ( - C — O ).

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2031, 1984 DOI: 10.1021/jo00185a045

InChI:InChI=1/C13H16O2/c1-3-14-13(15-4-2)11-10-12-8-6-5-7-9-12/h5-9,13H,3-4H2,1-2H3

Upstream product

• 62761-29-9 3-chloropropargyl aldehyde diethyl acetal 
• 6738-06-3 phenylethynylmagnesium bromide 
• 122-51-0 orthoformic acid triethyl ester 
• 536-74-3 phenylacetylene 
• 14444-77-0 diethyl phenyl orthoformate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 64-17-5 ethanol 
• 115525-21-8 gem-2-bromo-2-phenyl-1,1-dichlorocyclopropane 
• 178425-56-4 1,1,2-tribromo-2-phenylcyclopropane 
• 2579-22-8 Phenylpropargyl aldehyde 
• 10160-87-9 Propiolaldehyde diethyl acetal 
• 2996-92-1 phenyl trimethylsiloxane 
• 20461-86-3 2,2-diethoxy acetic acid 
• 98-81-7 1-bromovinylbenzene 

Downstream Products

• 19307-89-2 1-Phenyl-2-diethoxymethylcyclopropen-2-on 
• 14499-26-4 2-Acetyl-3-ethoxy-2-methyl-5-phenyl-pent-4-ynoic acid methyl ester 
• 16807-58-2 C₂₁H₂₀O₄ 
• 183614-20-2 1-(1,2,4-triazol-1-yl)-3-phenylpropargyl ethyl ether 
• 180967-67-3 1,6-diphenyl-hexa-1,5-diyne-3,4-dione 
• 180967-70-8 1-phenyl-6-triisopropylsilyl-hexa-1,5-diyne-3,4-dione 
• 251481-79-5 rel-(2R,3S,4R)-4,5-dimethyl-2-phenylethylnyl-1,3-dioxolane 
• 195374-93-7 rel-(2S,3S,4R)-4,5-dimethyl-2-phenylethylnyl-1,3-dioxolane 
• 210104-36-2 (S)-3-((1R,2S)-1-Ethyl-2-hydroxy-butoxy)-5-phenyl-pent-4-ynethioic acid S-tert-butyl ester 
• 195374-94-8 (2S,4R,5S)-4,5-Diethyl-2-phenylethynyl-[1,3]dioxolane 
• 210104-28-2 (2S,4R,5S)-2-Phenylethynyl-4,5-dipropyl-[1,3]dioxolane 
• 25226-98-6 trans-cinnamaldehyde diethylacetal 
• 104-53-0 3-phenyl-propionaldehyde 
• 268226-22-8 2,5-diphenyl-3,4-dimethyl-6-formyl-1-phosphanorborna-2,5-diene 

Relevant articles and documents

-

-

Lewis-acid-catalyzed asymmetric alkynylation of alkynyl 1,2-diketones: Controllable formation of 3(2 H)-furanones and α-hydroxy ketones

We report the highly regio- and enantioselective alkynylation of alkynyl 1,2-diketones under Lewis acid catalysis, leading to the formation of a series of biologically important 3(2H)-furanones with high to excellent ee values. Moreover, a slight change of the reaction conditions produces a range of highly functionalized α-hydroxy ketones with a high level of enantioselectivity. A variety of further transformations can be easily achieved, demonstrating the synthetic potential of this protocol.

Blue light photoredox-catalysed acetalation of alkynyl bromides

Herein, we report an organo-photoredox-based protocol using 2,2-diethoxyacetic acid as the acetal source to achieve acetalation of alkynyl bromides to afford various alkynyl acetal products. In addition to arylethynyl bromides, substrates bearing heteroaryl rings (thiophene, pyridine, and indole) smoothly gave the corresponding acetalation products. This mild protocol has potential utility for the synthesis of aldehydes by further protonization.

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.