4-Hex-1-ynylbenzonitrile

Base Information

• Chemical Name: 4-Hex-1-ynylbenzonitrile
• CAS No.: 175203-91-5
• Molecular Formula: C13H13 N
• Molecular Weight: 183.253
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID90381411
• Nikkaji Number: J1.116.557E
• Wikidata: Q82172209
• Mol file: 175203-91-5.mol

Synonyms:4-hex-1-ynylbenzonitrile;175203-91-5;4-(hex-1-yn-1-yl)benzonitrile;Benzonitrile, 4-(1-hexyn-1-yl)-;2,5-Dihydroxy-benzoicacid;4-(1-Hexynyl)benzonitrile;4-Hex-1-ynyl-benzonitrile;SCHEMBL2232067;DTXSID90381411;BUHLQBAAYDTBOA-UHFFFAOYSA-N;Benzonitrile,4-(1-hexyn-1-yl)-;AKOS015908487

Chemical Property of 4-Hex-1-ynylbenzonitrile

Chemical Property:

• Vapor Pressure: 0.00063mmHg at 25°C
• Boiling Point: 309.7oC at 760 mmHg
• Flash Point: 141.6oC
• PSA: 23.79000
• Density: 1g/cm3
• LogP: 3.09998
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

99%min ^*data from raw suppliers

4-HEX-1-YNYLBENZONITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC#CC1=CC=C(C=C1)C#N

Technology Process of 4-Hex-1-ynylbenzonitrile

There total 14 articles about 4-Hex-1-ynylbenzonitrile 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: 99.0%

4-bromobenzenecarbonitrile (623-00-7) + potassium (1-hexyn-1-yl)trifluoroborate → 4-(hex-1-yn-1-yl)benzonitrile (175203-91-5)

Guidance literature:

With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; water; for 12h; Heating;

DOI:10.1021/jo0262356

Reference yield: 93.0%

4-iodobenzonitrile (3058-39-7) + hex-1-yne (693-02-7) → 4-(hex-1-yn-1-yl)benzonitrile (175203-91-5)

Guidance literature:

With C₁₆H₂₀Cl₂N₂O₂Pd; potassium hydroxide; In water; acetonitrile; at 60 ℃; for 3h;

DOI:10.1016/j.tetlet.2015.12.086

Reference yield: 90.0%

4-cyanophenyl trifluoromethanesulfonate (66107-32-2) + potassium (1-hexyn-1-yl)trifluoroborate → 4-(hex-1-yn-1-yl)benzonitrile (175203-91-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; isopropyl alcohol; at 100 ℃; for 0.25h; Microwave irradiation;

DOI:10.1016/j.tetlet.2007.08.002

upstream raw materials:

4-bromobenzenecarbonitrile

4-Cyanochlorobenzene

hex-1-yne

4-iodobenzonitrile

Downstream raw materials:

(E)-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tributylstannyl)hex-1-en-1-yl)benzonitrile

C₁₃H₁₅NO

Refernces

• 1、 Kandasamy, Mohanraj,Huang, Yu- Hsuan,Ganesan, Balaji,Senadi, Gopal Chandru,Lin, Wei-Yu. "In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor". . p. 4349 - 4356. Retrieved 2019/07/03.
• 2、 Ibrahim, Mansur B.,Ali, Bassam El,Malik, Imran,Fettouhi, Mohammed. "Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions". . p. 554 - 558. Retrieved 2016/01/20.