1-Methyl-4-(phenylethynyl)benzene

Base Information

• Chemical Name: 1-Methyl-4-(phenylethynyl)benzene
• CAS No.: 3287-02-3
• Molecular Formula: C15H12
• Molecular Weight: 192.26
• Hs Code.: 2902909090
• DSSTox Substance ID: DTXSID90186529
• Nikkaji Number: J462.221I
• Wikidata: Q83057842
• Mol file: 3287-02-3.mol

Synonyms:1-Methyl-4-(phenylethynyl)benzene;3287-02-3;1-methyl-4-(2-phenylethynyl)benzene;1-METHYL-4-PHENYLETHYNYL-BENZENE;4-Methyltolan;Benzene, 1-methyl-4-(phenylethynyl)-;MFCD00958208;4-Methyltolane;1-(2-p-Tolylethynyl)benzene;methyl 4-(phenylethynyl)benzene;DTXSID90186529;LENVYSAMNKKWEK-UHFFFAOYSA-N;AKOS005067652;1-methyl-4-(2-phenyl-ethynyl)-benzene;SY027311;M3021;A918809

Chemical Property of 1-Methyl-4-(phenylethynyl)benzene

Chemical Property:

• Vapor Pressure: 0.000877mmHg at 25°C
• Boiling Point: 314.1°Cat760mmHg
• Flash Point: 135.6°C
• PSA: 0.00000
• Density: 1.05g/cm³
• LogP: 3.39480
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 192.093900383
• Heavy Atom Count: 15
• Complexity: 238

Purity/Quality:

97% ^*data from raw suppliers

1-Methyl-4-(phenylethynyl)benzene 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C#CC2=CC=CC=C2

Technology Process of 1-Methyl-4-(phenylethynyl)benzene

There total 246 articles about 1-Methyl-4-(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: 95.0%

4-tolyl iodide (624-31-7) + phenylpropyolic acid (637-44-5) → 1,4-diphenyl-1,3-butadiyne (886-66-8) + 4-(phenylethynyl)toluene (3287-02-3)

Guidance literature:

With sodium carbonate; In dimethyl sulfoxide; at 100 ℃; for 12h;

DOI:10.1016/j.catcom.2017.05.025

Reference yield: 78.0%

phenylacetylene (536-74-3) + p-toluenesulfonyl chloride (98-59-9) → 1,4-diphenyl-1,3-butadiyne (886-66-8) + 4-(phenylethynyl)toluene (3287-02-3)

Guidance literature:

With copper(l) iodide; triethylamine; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; Further Variations:; Catalysts; Reagents; Solvents; Product distribution; Heating;

DOI:10.1002/adsc.200404146

Reference yield: 78.0%

1-(2-bromoethynyl)-4-methylbenzene (33491-05-3) + diethyl(phenyl)aluminium (56280-66-1) → biphenyl (92-52-4,1594-86-1) + 4-(phenylethynyl)toluene (3287-02-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 60 ℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1016/j.tet.2018.08.050

upstream raw materials:

1,1-dichloro-2-phenyl-2-p-tolyl-ethene

copper(I) phenylacetylenide

4-tolyl iodide

1-(benzotriazol-1-yl)-1-(p-tolyl)-2-phenylethylene

Downstream raw materials:

(E)-1-(2-phenylethenyl)-4-(phenylethynyl)benzene

7,10-Dimethyl-8-phenyl-9-p-tolyl-fluoranthene

2-phenyl-1-p-tolyl-ethanone

Refernces

• 1、 Motti, Elena,Rossetti, Manuela,Bocelli, Gabriele,Catellani, Marta. "Palladium catalyzed multicomponent reactions in ordered sequence: New syntheses of o,o′-dialkylsubstituted diarylacetylenes and diarylalkylidenehexahydromethanofluorenes". . p. 3741 - 3749. Retrieved 2004.
• 2、 Ren, Tianrui,Zhang, Ye,Zhu, Weiwen,Zhou, Jiaju. "Copper-free, efficient, palladium (II)-catalyzed coupling of unactivated aryl iodides with terminal alkynes". . p. 3279 - 3290. Retrieved 2007.
• 3、 Trivedi, Manoj,Singh, Gurmeet,Kumar, Abhinav,Rath, Nigam P.. "A thiocyanato-bridged copper(i) cubane complex and its application in palladium-catalyzed Sonogashira coupling of aryl halides". . p. 12849 - 12852. Retrieved 2013.
• 4、 Granier,Cardenas,Echavarren. "Palladium-catalyzed reaction of a sterically constrained trialkyne: A dimerization-type reaction with a surprising finale". . p. 6775 - 6779. Retrieved 2000.
• 5、 Lokolkar, Manjunath S.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.. "Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes". . . Retrieved 2021/06/25.
• 6、 Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh. "Versatile and an efficient Sonogashira coupling reaction catalyzed with modified Pd-functionalized TMU-16 as a novel and reusable nanocatalyst". . . Retrieved 2021/07/24.