80151-33-3

Usage

Uses

Used in Pharmaceutical Synthesis:
3-(3-Chlorophenyl)prop-2-yn-1-ol is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. Its presence in these compounds can contribute to the development of new medications with specific therapeutic properties.
Used in Agrochemical Production:
In the agrochemical industry, 3-(3-Chlorophenyl)prop-2-yn-1-ol serves as a building block for the creation of pesticides and other crop protection agents. Its chemical properties allow it to be a component in the formulation of effective and targeted agrochemicals.
Used in Organic Compounds Production:
3-(3-Chlorophenyl)prop-2-yn-1-ol is utilized as a precursor in the production of organic compounds such as dyes, fragrances, and flavoring agents. Its unique structure lends itself to the creation of a wide array of specialty chemicals used in various consumer products.
Used in Antifungal and Antimicrobial Applications:
3-(3-Chlorophenyl)prop-2-yn-1-ol has been studied for its potential antifungal and antimicrobial properties, making it a candidate for use in applications where control of microbial growth is necessary, such as in medical, food preservation, and industrial settings.

InChI:InChI=1/C9H7ClO/c10-9-5-1-3-8(7-9)4-2-6-11/h1,3,5,7,11H,6H2

Upstream product

• 50-00-0 formaldehyd 
• 766-83-6 m-chlorophenylacetylene 
• 625-99-0 3-iodochlorobenzene 
• 107-19-7 propargyl alcohol 
• 108-37-2 1-bromo-3-chlorobenzene 

Downstream Products

• 1026840-30-1 1-(3-bromoprop-1-ynyl)-3-chlorobenzene 
• 1391710-79-4 6-(1-(3-chlorophenyl)propa-1,2-dienyl)-6-methyltetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent

Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.

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.

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.

Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst

The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions.

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.).

Nickel(II)-Catalyzed Asymmetric Propargyl [2,3] Wittig Rearrangement of Oxindole Derivatives: A Chiral Amplification Effect

A highly enantioselective [2,3] Wittig rearrangement of oxindole derivatives was realized by using a chiral N,N′-dioxide/NiII complex as the catalyst under mild reaction conditions. A strong chiral amplification effect was observed, and allowed access to chiral 3-hydroxy 3-substituted oxindoles bearing allenyl groups in high yields and enantioselectivities (up to 92 % ee) by using a ligand with only 15 % ee. A reasonable explanation was given based on the experimental investigations and X-ray crystal structures of enantiomerically pure and racemic catalysts. Moreover, the first catalytic kinetic resolution of racemic oxindole derivatives by a [2,3] Wittig rearrangement was realized with high efficiency and stereoselectivity.

Gold(I)-Initiated Cycloisomerization/Diels-Alder/Retro-Diels-Alder Cascade Strategy to Biaryls

A unique approach to biaryls was developed on the basis of propargyl vinyl ethers and dienophiles substrates via a gold(I)-initiated cycloisomerization/Diels-Alder/retro-Diels-Alder cascade reaction. The scope and mechanism of the reaction were investigated on the basis of a series of synthetic substrates, control experiments, and DFT calculations.

Facile synthesis of substituted 3-aminofurans through a tandem reaction of N-sulfonyl-1,2,3-triazoles with propargyl alcohols

A relay catalysis strategy for substituted 3-aminofurans synthesis has been developed. This transformation involves a tandem reaction sequence through aza-vinyl-rhodium(ii) carbene O-H bond insertion, thermal propargyl-Claisen rearrangement and gold(i)-catalyzed intramolecular cyclization. More importantly, the current strategy employs simple feedstocks as starting materials, providing substituted 3-aminofurans in a highly efficient manner.

Zinc-catalyzed [4+3] cycloaddition with concomitant furan annulation: Formation of cyclohepta[b]furans

A convenient zinc-promoted [4+3] cycloaddition of a carbonyl ene-yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of C-O bonds and C-C bonds. Go tandem! A first zinc-catalyzed tandem [4+3] cycloaddition is presented herein. Various substituted cyclohepta[b]furans were synthesized from carbonyl ene-yne and diene in moderate to good yield. Furan rings and seven-membered rings were prepared in one single step (see scheme; TBS=tert-butyldimethyl).

Lactone radical cyclizations and cyclization cascades mediated by SmI 2-H2O

Unsaturated lactones undergo reductive radical cyclizations upon treatment with SmI2-H2O to give decorated cycloheptanes in a single highly selective operation during which up to three contiguous stereocenters are generated. Furthermore, cascade processes involving lactones bearing two alkenes, an alkene and an alkyne, or an allene and an alkene allow "one-pot" access to biologically significant molecular scaffolds with the construction of up to four contiguous stereocenters. The cyclizations proceed by the trapping of radical anions formed by electron transfer reduction of the lactone carbonyl.