Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-

Base Information

• Chemical Name: Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-
• CAS No.: 100752-58-7
• Molecular Formula: C16H9NO
• Molecular Weight: 231.254
• DSSTox Substance ID: DTXSID30470939
• Nikkaji Number: J2.241.556E
• Wikidata: Q82299161
• Mol file: 100752-58-7.mol

Synonyms:100752-58-7;4-(3-phenylpropioloyl)benzonitrile;UNM-0000306057;Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-;4-(3-phenylprop-2-ynoyl)benzonitrile;SCHEMBL24809512;BDBM54699;DTXSID30470939;cid_11708441;4-(1-oxo-3-phenylprop-2-ynyl)benzonitrile;4-(3-phenylprop-2-ynoyl)benzenecarbonitrile;UNM000011087301

Chemical Property of Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 231.068413911
• Heavy Atom Count: 18
• Complexity: 402

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC(=O)C2=CC=C(C=C2)C#N

Technology Process of Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)-

There total 25 articles about Benzonitrile, 4-(1-oxo-3-phenyl-2-propynyl)- 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: 98.0%

tributylstannylethynylbenzene (3757-88-8) + 4-cyanobenzoyl chlorIde (6068-72-0) → 1-(4-cyanophenyl)-3-phenylprop-2-yn-1-one (100752-58-7)

Guidance literature:

With bis[di(tert-butyl)chlorophosphine]palladium dichloride; In acetonitrile; at 82 ℃; for 20h;

DOI:10.1021/jo051257o

Reference yield: 97.2%

4-aminobenzyl cyanide (10406-25-4) + phenylacetylene (536-74-3) → 1-(4-cyanophenyl)-3-phenylprop-2-yn-1-one (100752-58-7)

Guidance literature:

With C₂₆H₃₆NP; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dimethyl sulfoxide; at 60 ℃; for 5h; Reagent/catalyst; Solvent;

Reference yield: 97.0%

C13H10N4O4 + phenylacetylene (536-74-3) → 1-(4-cyanophenyl)-3-phenylprop-2-yn-1-one (100752-58-7) + 2-hydroxy-4,6-dimethoxy-1,3,5-triazine (1075-59-8)

Guidance literature:

With palladium diacetate; In acetonitrile; at 50 ℃; for 10h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b01466

upstream raw materials:

tributylstannylethynylbenzene

4-cyanobenzoyl chlorIde

phenylacetylene

carbon monoxide

Downstream raw materials:

1-acetyl-5-(4-cyanophenyl)-5-hydroxy-3-phenyl-4,5-dihydro-1H-pyrazole

(Z)-1-(4-cyanophenyl)-3-phenyl-3-(phenylamino)prop-2-en-1-one

(E)-3-(3-(4-cyanophenyl)-5-phenylisoxazol-4-yl)-N,N-dimethylacrylamide

(Z)-4-(1-(methoxyimino)-3-phenylprop-2-yn-1-yl)benzonitrile

Refernces

• 1、 Chavan, Sujit P.,Varadwaj, G.Bishwa Bidita,Parida, Kulamani,Bhanage, Bhalchandra M.. "Palladium anchored on amine-functionalized K10 as an efficient, heterogeneous and reusable catalyst for carbonylative Sonogashira reaction". . p. 237 - 245. Retrieved 2015.
• 2、 Navidi, Mozhgan,Movassagh, Barahman. "Palladium chloride-cryptand-22 complex: An efficient catalyst for the copper-, phosphorus-, and solvent-free synthesis of ynones". . p. 1363 - 1367. Retrieved 2013.
• 3、 Thirukovela, Narasimha Swamy,Balaboina, Ramesh,Botla, Vinayak,Vadde, Ravinder,Jonnalagadda, Sreekantha Babu,Vasam, Chandra Sekhar. "One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization". . p. 6471 - 6481. Retrieved 2019.
• 4、 Charugandla, Renuka,Vangala, Markandeya Sarma,Chidara, Sridhar,Korupolu, Raghu Babu. "Nickel catalysed carbonylative Sonogashira reaction for the synthesis of diarylalkynones and 2-substituted flavones". . p. 3283 - 3287. Retrieved 2018.
• 5、 Ogiwara, Yohei,Kubota, Masahito,Kurogi, Kotaro,Konakahara, Takeo,Sakai, Norio. "Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using Indium(III) Bromide". . p. 18598 - 18600. Retrieved 2015.
• 6、 He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo. "Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones". supporting information. p. 457 - 466. Retrieved 2021/01/29.