4-(3-Hydroxyprop-1-ynyl)benzonitrile

Base Information

• Chemical Name: 4-(3-Hydroxyprop-1-ynyl)benzonitrile
• CAS No.: 80151-16-2
• Molecular Formula: C10H7NO
• Molecular Weight: 157.172
• European Community (EC) Number: 675-131-5
• DSSTox Substance ID: DTXSID70384925
• Nikkaji Number: J1.224.610B
• Wikidata: Q82177385
• Mol file: 80151-16-2.mol

Synonyms:4-(3-hydroxyprop-1-ynyl)benzonitrile;80151-16-2;4-(3-hydroxyprop-1-yn-1-yl)benzonitrile;4-(3-Hydroxy-prop-1-ynyl)-benzonitrile;3-(4-cyanophenyl)-2-propyne-1-ol;4-(3-hydroxy-1-propynyl)benzonitrile;SCHEMBL78831;DTXSID70384925;WUBRVKKUJQPDQN-UHFFFAOYSA-N;CCG-49276;MFCD00219780;AKOS004118138;FS-1809;CS-0331031;FT-0613661;J-513391;SR-01000638743-1

Chemical Property of 4-(3-Hydroxyprop-1-ynyl)benzonitrile

Chemical Property:

• Vapor Pressure: 0.000102mmHg at 25°C
• Refractive Index: 1.604
• Boiling Point: 324.2 °C at 760 mmHg
• Flash Point: 149.8 °C
• PSA: 44.02000
• Density: 1.2 g/cm³
• LogP: 0.90208
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 157.052763847
• Heavy Atom Count: 12
• Complexity: 241

Purity/Quality:

98%, ^*data from raw suppliers

4-(3-Hydroxyprop-1-yn-1-yl)benzonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#CCO)C#N

Technology Process of 4-(3-Hydroxyprop-1-ynyl)benzonitrile

There total 11 articles about 4-(3-Hydroxyprop-1-ynyl)benzonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

4-bromobenzenecarbonitrile (623-00-7) + propargyl alcohol (107-19-7) → 3-(4-cyanophenyl)-2-propyne-1-ol (80151-16-2)

Guidance literature:

With copper(l) iodide; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); Tedicyp; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/j.tetlet.2003.12.128

Reference yield: 96.0%

4-iodobenzonitrile (3058-39-7) + propargyl alcohol (107-19-7) → 3-(4-cyanophenyl)-2-propyne-1-ol (80151-16-2)

Guidance literature:

With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In toluene; at 35 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo1025578

Reference yield: 95.0%

1-trimethylsilyloxy-2-propyne (5582-62-7) + 4-iodobenzonitrile (3058-39-7) → 3-(4-cyanophenyl)-2-propyne-1-ol (80151-16-2)

Guidance literature:

With potassium carbonate; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 0.166667h; microwave irradiation;

DOI:10.1016/j.tetlet.2007.05.086

upstream raw materials:

4-bromobenzenecarbonitrile

propargyl alcohol

4-iodobenzonitrile

1-trimethylsilyloxy-2-propyne

Downstream raw materials:

4-(furan-3-yl)benzonitrile

4-(3-(3-p-tolylprop-2-ynylthio)prop-1-ynyl)benzonitrile

4-(3-(3-p-tolylprop-2-ynylsulfonyl)prop-1-ynyl)benzonitrile

4-(1H-pyrazol-3-yl)-benzonitrile

Refernces

• 1、 Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong. "Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes". supporting information. p. 6041 - 6045. Retrieved 2021/08/03.
• 2、 Díaz-Marta, Antonio S.,Ya?ez, Susana,Lasorsa, Eliana,Pacheco, Patricia,Tubío, Carmen R.,Rivas, José,Pi?eiro, Yolanda,Gómez, Manuel A. Gonzalez,Amorín, Manuel,Guitián, Francisco,Coelho, Alberto. "Integrating Reactors and Catalysts through Three-Dimensional Printing: Efficiency and Reusability of an Impregnated Palladium on Silica Monolith in Sonogashira and Suzuki Reactions". . p. 1762 - 1771. Retrieved 2020/02/15.