80151-16-2

Basic information

• Product Name: 4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE
• Synonyms: AKOS PRN-0103;4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE;4-(3-HYDROXY-1-PROPYNYL)BENZONITRILE;3-(4-CYANOPHENYL)PROP-2-YN-1-OL
• CAS NO: 80151-16-2
• Molecular Formula: C₁₀H₇NO
• Molecular Weight: 157.17
• Mol File: 80151-16-2.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 324.2 °C at 760 mmHg
• Flash Point: 149.8 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 0.000102mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(80151-16-2)
• EPA Substance Registry System: 4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE(80151-16-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 80151-16-2(Hazardous Substances Data)

Usage

General Description

4-(3-Hydroxy-prop-1-ynyl)-benzonitrile is a chemical compound with the molecular formula C10H7NO. It is a yellowish crystalline powder that is insoluble in water but soluble in organic solvents. 4-(3-HYDROXY-PROP-1-YNYL)-BENZONITRILE is used in organic synthesis as a building block for the preparation of various biologically active compounds and pharmaceuticals. It is also used as a precursor for the synthesis of heterocyclic compounds and as a reagent in chemical research. Additionally, it has been studied for its potential biological activities, including its anti-inflammatory and antiproliferative properties. Overall, 4-(3-Hydroxy-prop-1-ynyl)-benzonitrile is a versatile chemical with diverse applications in both research and industry.

InChI:InChI=1/C10H7NO/c11-8-10-5-3-9(4-6-10)2-1-7-12/h3-6,12H,7H2

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 107-19-7 propargyl alcohol 
• 3058-39-7 4-iodobenzonitrile 
• 5582-62-7 1-trimethylsilyloxy-2-propyne 
• 623-03-0 4-Cyanochlorobenzene 
• 19070-80-5 n-<(trimethylsiloxy)methyl>phthalimide 
• 75867-40-2 4-[2-(trimethylsilyl)ethynyl]benzonitrile 

Downstream Products

• 3032-92-6 4-cyanophenylacetylene 
• 210885-01-1 4-(3-bromoprop-1-yn-1-yl)benzonitrile 
• 207119-82-2 4-(furan-3-yl)benzonitrile 
• 62043-82-7 4-Cyanobenzylhydroxymethylketon 
• 83101-12-6 4-(3-Hydroxypropyl)benzonitrile 
• 1268381-70-9 4-(3-(3-p-tolylprop-2-ynylthio)prop-1-ynyl)benzonitrile 
• 1268381-65-2 4-(3-(3-p-tolylprop-2-ynylsulfonyl)prop-1-ynyl)benzonitrile 
• 1190060-36-6 4-(3-oxo-1-propyn-1-yl)benzonitrile 

Relevant articles and documents

Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions

A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-

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.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.