67228-76-6

Basic information

• Product Name: 2-Propynal, 3-(4-chlorophenyl)-
• CAS NO: 67228-76-6
• Molecular Formula: C9H5ClO
• Molecular Weight: 164.591
• Mol File: 67228-76-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Propynal, 3-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propynal, 3-(4-chlorophenyl)-(67228-76-6)
• EPA Substance Registry System: 2-Propynal, 3-(4-chlorophenyl)-(67228-76-6)

Safety Data

• Hazardous Substances Data: 67228-76-6(Hazardous Substances Data)

Upstream product

• 873-73-4 4-n-chlorophenylacetylene 
• 68-12-2 N,N-dimethyl-formamide 
• 637-87-6 1-Chloro-4-iodobenzene 
• 104-88-1 4-chlorobenzaldehyde 
• 37614-57-6 3-(4-chlorophenyl)prop-2-yn-1-ol 
• 77295-59-1 1-chloro-4-(2,2-dibromovinyl)benzene 

Downstream Products

• 133793-08-5 benzyl 4-chlorocinnamate 
• 1071813-78-9 C₉H₆ClN₃O 
• 1228931-76-7 methyl 5-(4-chlorophenyl)-3-hydroxy-2-methylene-pent-4-ynoate 
• 1258886-23-5 C₁₁H₁₀ClNO₃ 
• 1257518-26-5 4-(4-chlorophenylethynyl)oxetan-2-one 
• 1392207-19-0 p-chlorophenylbuta-1,3-diynyl methyl sulfide 
• 1446871-26-6 (E)-1-methylthio-1-phenylsulphonyl-(4-(4-chloro)phenyl)-1-butene-3-yne 
• 1604677-06-6 C₁₈H₁₂ClNO₃ 

Relevant articles and documents

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

Organocatalytic Regio- and Enantioselective N-Alkylation of Isoxazol-5-ones

A chiral phosphoric acid catalyzed regio- and enantioselective reaction between 1-acylamino-3-arylprop-2-yn-1-ols and isoxazol-5-ones has been developed for the first time. With the established protocol, N-alkylation of isoxazol-5-ones was achieved, affording enantioenriched N,N-acetals in 74–99 % yield with 72–88 % ee.

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.

Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes

A copper-catalyzed silylation of propargyl dichlorides was developed to access chloro-substituted allenylsilanes under mild reaction conditions. Moreover, enantioenriched chloro-substituted allenylsilanes can be synthesized in moderate to high yields and good enantioselectivities with this protocol.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Applications of Thermal Activation, Ball-milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides

Stereoselective addition of nitromethane to conjugated en-ynones was performed through the application of chiral squaramides. Three non-classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball-milling. Hydrogen-bonding catalysis was effective in all these methods, providing 1,4-addition products in high yields and stereoselectivities of up to 98% requiring 1–5 mol% of Cinchona alkaloid squaramide. (Figure presented.).

Base-Promoted Tandem Cyclization for the Synthesis of Benzonitriles by C?C Bond Construction

A facile synthesis of benzonitriles via a base-promoted tandem cyclization reaction of α,β-unsaturated enones having electron-withdrawing group (EWG) and 2-acyl-acrylonitriles was developed. This new synthetic method to access benzonitriles is suitable for a wide range of substrates. A plausible reaction mechanism is proposed on the basis of previous literature and our own investigations. (Figure presented.).

Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles to Construct a Pyrrole Core

This work reports gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles or benzisoxazoles to yield pyrrole derivatives. The reaction chemoselectivity is controlled by an initial attack of an isoxazole at a less hindered alkyne to form gold carbenes, further inducing a 1,2-migration of a second alkyne group. A broad substrate scope of 1,4-diyn-3-ols, isoxazoles and even benzisoxazoles highlighted the reaction utility.

Regioselective Synthesis of Indene from 3-Aryl Propargylic gem-Dipivalates Catalyzed by N-Heterocyclic Carbene Gold(I) Complexes

1-Aryl-3,3-bis(pivaloyloxy)propynes can be converted in good to high yields into either 1,3- or 1,2-bis(pivaloyloxy)indenes, depending on the N-heterocyclic carbene (NHC) gold(I) hexafluoroantimonate catalyst used. Almost exclusive formation of 1,3-di(oxycarbonyl)indene derivatives was achieved with cationic gold complexes containing the embracing N,N′-1,3-bis(9-butylfluorenyl)benzimidazolylidene ligand (nBuFNHC). The regioselective issue of the reaction was rationalized by the specific spatial distribution of the steric bulk in the nBuFNHC ligand. In contrast, only modest selectivities in favor of 1,2-disubstituted indenes were observed with more classical NHC gold complexes, the best selectivity being then obtained with N,N′-1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolylidene gold chloride (SIPrAuCl) as precatalyst. (Figure presented.).