1-Chloro-2-(phenylethynyl)benzene

Base Information

• Chemical Name: 1-Chloro-2-(phenylethynyl)benzene
• CAS No.: 10271-57-5
• Molecular Formula: C14H9 Cl
• Molecular Weight: 212.678
• Hs Code.: 2903999090
• DSSTox Substance ID: DTXSID00145465
• Nikkaji Number: J146.403E
• Wikidata: Q83010026
• Mol file: 10271-57-5.mol

Synonyms:1-chloro-2-(2-phenylethynyl)benzene;1-CHLORO-2-(PHENYLETHYNYL)BENZENE;10271-57-5;Acetylene, (o-chlorophenyl)phenyl-;1-Phenyl-2-(2-chlorophenyl)ethyne;Benzene, 1-chloro-2-(phenylethynyl)-;Chloro(phenylethynyl)benzene;(o-Chlorophenyl)phenylacetylene;SCHEMBL1920654;2-(Phenylethynyl)phenyl chloride;1-chloro-2-phenylethynyl-benzene;DTXSID00145465;1-Chloro-2-(phenylethynyl)benzene #;90077-73-9

Chemical Property of 1-Chloro-2-(phenylethynyl)benzene

Chemical Property:

• Vapor Pressure: 0.000249mmHg at 25°C
• Boiling Point: 334.4°Cat760mmHg
• Flash Point: 150.8°C
• PSA: 0.00000
• Density: 1.19g/cm³
• LogP: 3.73980
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 212.0392780
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

98%,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#CC2=CC=CC=C2Cl

Technology Process of 1-Chloro-2-(phenylethynyl)benzene

There total 30 articles about 1-Chloro-2-(phenylethynyl)benzene 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: 100.0%

2-iodochlorobenzene (615-41-8) + phenylacetylene (536-74-3) → 1-chloro-2-(2-phenylethynyl)benzene (10271-57-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 30 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.3762/bjoc.12.187

Reference yield: 94.0%

iodobenzene (591-50-4) + 2-chlorophenylacetylene (873-31-4) → 1-chloro-2-(2-phenylethynyl)benzene (10271-57-5)

Guidance literature:

With copper(l) iodide; palladium; triphenylphosphine; aluminum oxide; potassium fluoride; for 0.0416667h; microwave irradiation;

DOI:10.1016/S0040-4020(01)00774-8

Reference yield: 94.0%

1-benzyl-1H-benzotriazole (4706-43-8) + 2-chloro-benzaldehyde (89-98-5) → 1-chloro-2-(2-phenylethynyl)benzene (10271-57-5)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 60 ℃; for 18h; Inert atmosphere;

DOI:10.1039/d1ob00627d

upstream raw materials:

2-chloro-benzil-dihydrazone

silver benzoate

1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-ethanesulfonic acid 2-chloro-phenyl ester

phenylacetylene

Downstream raw materials:

1-(n-octyl)-2-phenyl-1H-indole

1-n-hexyl-2-phenyl-1H-indole

C₅H₄NCHCSn(C₄H₉)3C₆H₄(o-Cl)

1-adamantan-1-yl-2-phenyl-1H-indole

Refernces

• 1、 Fabrizi, Giancarlo,Goggiamani, Antonella,Sferrazza, Alessio,Cacchi, Sandro. "Sonogashira cross-coupling of arenediazonium salts". . p. 4067 - 4070. Retrieved 2010.
• 2、 Hajipour, Abdol R.,Rafiee, Fatemeh. "(BeDABCO)2Pd2Cl6 as an efficient homogeneous catalyst for copper-free Sonogashira cross-coupling reaction". . p. 595 - 597. Retrieved 2014.
• 3、 Novak, Zoltan,Nemes, Peter,Kotschy, Andras. "Tandem Sonogashira coupling: An efficient tool for the synthesis of diarylalkynes". . p. 4917 - 4920. Retrieved 2004.
• 4、 Ji, Yuan,Zhong, Ning,Kang, Zinan,Yan, Guobing,Zhao, Ming. "Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes". . p. 209 - 214. Retrieved 2018.
• 5、 Kim, Suhong,Rojas-Martin, Jaime,Toste, F. Dean. "Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling". . p. 85 - 88. Retrieved 2015.
• 6、 Balsane, Kishor E.,Shendage, Suresh S.,Nagarkar, Jayashree M.. "Efficient Sonogashira and Suzuki-Miyaura coupling reaction catalyzed by Pd-Nanoparticles". . p. 425 - 431. Retrieved 2015.
• 7、 Basavaprabhu,Samarasimhareddy,Prabhu, Girish,Sureshbabu, Vommina V.. "A simple and greener approach for the synthesis of PVC supported Pd (0): Application to Heck and Sonogashira reactions in water". . p. 2256 - 2260. Retrieved 2014.
• 8、 Wang, Xian,Wang, Zhenhua,Xie, Zunyuan,Zhang, Guofang,Zhang, Weiqiang,Gao, Ziwei. "Functionalized α,β-ynones: Efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction". . p. 109296 - 109300. Retrieved 2016.
• 9、 Kaspar, Ludwig T.,Ackermann, Lutz. "Three-component indole synthesis using ortho-dihaloarenes". . p. 11311 - 11316. Retrieved 2005.
• 10、 Park, Jaerim,Song, Kwang Ho,Lee, Sunwoo. "Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide". . p. 3197 - 3204. Retrieved 2018.