19115-29-8

Basic information

• Product Name: 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL
• Synonyms: 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL
• CAS NO: 19115-29-8
• Molecular Formula: C₉H₇ClO
• Molecular Weight: 166.60428
• Mol File: 19115-29-8.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL(19115-29-8)
• EPA Substance Registry System: 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL(19115-29-8)

Safety Data

• Hazardous Substances Data: 19115-29-8(Hazardous Substances Data)

Usage

General Description

1-(2-Chloro-phenyl)-prop-2-yn-1-ol, also known as 2-Chlorophenylpropargyl alcohol, is a chemical compound with the molecular formula C9H7ClO. It is an organic compound with a molecular weight of 166.6 g/mol. 1-(2-CHLORO-PHENYL)-PROP-2-YN-1-OL is an alkyne and contains both an alcohol and a chloro group. It is commonly used in organic synthesis and as a building block in the production of pharmaceuticals and agrochemicals. It is also used as a reagent in chemical reactions, particularly in the formation of carbon-carbon triple bonds. Additionally, it has applications in the production of fine chemicals and as a precursor in the synthesis of various chemical compounds.

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 1066-54-2 trimethylsilylacetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-26-8 sodium acetylide 

Downstream Products

• 1008132-31-7 4-(2-chlorophenyl)-2,5-dimethyl-1-phenylpyrrole-3-carboxylic acid ethyl ester 
• 1261268-15-8 methyl (E)-3-(1-(2-chlorophenyl)prop-2-ynyloxy)acrylate 
• 1262149-00-7 1-(2-chlorophenyl)-2-oxopropyl acetate 
• 1186338-21-5 1-(2-chlorophenyl)prop-2-ynyl acetate 
• 1307885-90-0 1-(2-chlorophenyl)-5-methylhex-5-en-2-yn-1-ol 
• 1352957-92-6 (3-(2-chlorophenyl)pent-1-en-4-yne-1,1-diyl)dibenzene 
• 1443225-38-4 (1-benzyl-1H-1,2,3-triazol-4-yl)(2-chlorophenyl)methanone 
• 1582792-93-5 1-(2-chlorophenyl)prop-2-yn-1-yl morpholine-4-carboxylate 
• 1794-45-2 (E)-3-(2-chlorophenyl)propenal 
• 1361251-86-6 (R)-1-(2-chlorophenyl)buta-2,3-dien-1-ol 
• 141077-51-2 (R)-2-(2-chlorophenyl)-2,5-dihydrofuran 
• 141077-51-2 (S)-2-(2-chlorophenyl)-2,5-dihydrofuran 

Relevant articles and documents

Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(i)/Pd(0) catalysts in a similar reaction pathway.

A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles

A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.