4-Methylbiphenyl

Base Information

• Chemical Name: 4-Methylbiphenyl
• CAS No.: 644-08-6
• Molecular Formula: C13H12
• Molecular Weight: 168.238
• Hs Code.: 29029090
• European Community (EC) Number: 211-409-0
• NSC Number: 407669
• UNII: 13J700766D
• DSSTox Substance ID: DTXSID4047177
• Nikkaji Number: J2.382.522H,J36.116J
• Wikidata: Q27160322
• Metabolomics Workbench ID: 45649
• ChEMBL ID: CHEMBL3187976
• Mol file: 644-08-6.mol

Synonyms:4-Methylbiphenyl;644-08-6;4-Phenyltoluene;4-METHYL-1,1'-BIPHENYL;1-Methyl-4-phenylbenzene;p-Methylbiphenyl;1,1'-Biphenyl, 4-methyl-;p-Methyldiphenyl;4-Methyldiphenyl;Biphenyl, 4-methyl-;p-Phenyltoluene;(4-Methylphenyl)benzene;FEMA 3186;4-methyl-biphenyl;Phenyltoluene, p-;FEMA No. 3186;Methylphenylbenzene, p-;4-methyl biphenyl;NSC 407669;EINECS 211-409-0;BRN 1904468;DTXSID4047177;CHEBI:88448;UNII-13J700766D;MFCD00008544;NSC-407669;13J700766D;4-05-00-01860 (Beilstein Handbook Reference);p-Tolylbenzene;p-Methylphenylbenzene;4-methyl-1;Cc1ccc(cc1)c2ccccc2;methyl biphenyl (4-);4-Phenyltoluene, 98%;4-(4-methylphenyl)benzene;METHYLBIPHENYL, 4-;4-Phenyltoluene, >=98%;P-METHYLBIPHENYL [FHFI];Biphenyl-4-ylmethylidyne radical;CHEMBL3187976;DTXCID2027177;ZZLCFHIKESPLTH-UHFFFAOYSA-;Tox21_302610;NSC407669;STK291008;AKOS003364076;CS-W017793;HY-W017077;LS-2905;NCGC00256690-01;AC-13456;AS-13072;CAS-644-08-6;SY049485;1-methyl-4-phenyl-benzene;FT-0618978;M0563;A834745;W-104843;Q27160322

Chemical Property of 4-Methylbiphenyl

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.0132mmHg at 25°C
• Melting Point: 44-47 °C(lit.)
• Refractive Index: 1.564
• Boiling Point: 267.799 °C at 760 mmHg
• Flash Point: 117.819 °C
• PSA: 0.00000
• Density: 0.984 g/cm³
• LogP: 3.66200
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water. Soluble in alcohol and ether, very soluble in organic solvents.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 168.093900383
• Heavy Atom Count: 13
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-Phenyltoluene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: CC1=CC=C(C=C1)C2=CC=CC=C2
• Description: Prepared by catalytic reduction of p-phenyl benzyl alcohol obtained from p-phenyl benzoic acid.
• Uses: 4-Phenyltoluene is used as a flavoring ingredient in the food industry. It also functions as a reagent used in organic and pharmaceutical synthesis.

Technology Process of 4-Methylbiphenyl

There total 976 articles about 4-Methylbiphenyl 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%

chlorobenzene (108-90-7) + para-methylphenylmagnesium bromide (4294-57-9) → biphenyl (92-52-4,1594-86-1) + (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + 4-Methylbiphenyl (644-08-6)

Guidance literature:

With FeF₃*H₂O; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In tetrahydrofuran; at 20 - 60 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja9039289

Reference yield: 85.0%

iodobenzene (591-50-4) + 4-methylphenylboronic acid (5720-05-8) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + 4-Methylbiphenyl (644-08-6)

Guidance literature:

With trans-1,2-Diaminocyclohexane; potassium tert-butylate; silver(I) acetate; In dimethyl sulfoxide; at 150 ℃; for 13h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.09.127

Reference yield: 82.0%

para-bromotoluene (106-38-7) + phenyl trimethylsiloxane (2996-92-1,46143-12-8) → (4,4'-dimethyl-1,1'-biphenyl) (613-33-2) + 4-Methylbiphenyl (644-08-6)

Guidance literature:

With tetrabutyl ammonium fluoride; triphenylphosphine; palladium diacetate; In tetrahydrofuran; N,N-dimethyl-formamide; at 90 ℃; for 24h;

DOI:10.1021/ol991186d

upstream raw materials:

sodium tetraphenyl borate

formic acid

4t-methyl-1-phenyl-4c-trichloromethyl-cyclohexa-2,5-dien-r-ol

bromobenzene

Downstream raw materials:

4-nitro-4'-methyl-1,1'-biphenyl

4'-methylbiphenyl-4-sulfonic acid

4-Phenylbenzaldehyde

biphenyl-4-carboxylic acid

Refernces

• 1、 Holzer, Christof,Dupé, Antoine,Peschel, Lydia M.,Belaj, Ferdinand,M?sch-Zanetti, Nadia C.. "Mercaptoaryl-Oxazoline Complexes of Palladium and Their High Activities as Catalysts for Suzuki–Miyaura Coupling Reactions in Water". . p. 568 - 575. Retrieved 2018.
• 2、 Lichtenegger,Maier,Hackl,Khinast,G?ssler,Griesser,Kumar, V.S. Phani,Gruber-Woelfler,Deshpande. "Suzuki-Miyaura coupling reactions using novel metal oxide supported ionic palladium catalysts". . p. 39 - 51. Retrieved 2017.
• 3、 Liu, Mengmeng,Zhu, Xiaohang,Wu, Li,Zhou, Xingchun,Li, Jing,Ma, Jiantai. "An efficient and reusable catalyst for Suzuki cross-coupling reactions in aqueous solution - Hollow palladium-ferrum bimetallic magnetic spheres". . p. 38264 - 38270. Retrieved 2015.
• 4、 Basappa Chidananda, Vasantha Kumar,Ramakrishna, Dileep,Kaur, Manpreet,Hosakere Doddarevanna, Revanasiddappa. "Benzimidazolyl based Schiff base palladium complex in an ionic liquid: an effective combination for Suzuki coupling". . p. 1573 - 1584. Retrieved 2017.
• 5、 Shaker, Masoumeh,Elhamifar, Dawood. "Core-shell structured magnetic mesoporous silica supported Schiff-base/Pd: An efficacious and reusable nanocatalyst". . p. 3445 - 3454. Retrieved 2020.
• 6、 Kim, Ja Young,Jo, Youngshin,Kook, Seong-Keun,Lee, Sunwoo,Choi, Hyun Chul. "Synthesis of carbon nanotube supported Pd catalysts and evaluation of their catalytic properties for C{single bond}C bond forming reactions". . p. 28 - 32. Retrieved 2010.
• 7、 Corma, Avelino,Das, Debashis,Garcia, Hermenegildo,Leyva, Antonio. "A periodic mesoporous organosilica containing a carbapalladacycle complex as heterogeneous catalyst for Suzuki cross-coupling". . p. 322 - 331. Retrieved 2005.
• 8、 Sakon, Akira,Ii, Ryoma,Hamasaka, Go,Uozumi, Yasuhiro,Shinagawa, Tsutomu,Shimomura, Osamu,Nomura, Ry?ki,Ohtaka, Atsushi. "Detailed Mechanism for Hiyama Coupling Reaction in Water Catalyzed by Linear Polystyrene-Stabilized PdO Nanoparticles". . p. 1618 - 1622. Retrieved 2017.
• 9、 Xiong, Gang,Chen, Xiao-Ling,You, Li-Xin,Ren, Bao-Yi,Ding, Fu,Dragutan, Ileana,Dragutan, Valerian,Sun, Ya-Guang. "La-Metal-Organic Framework incorporating Fe3O4 nanoparticles, post-synthetically modified with Schiff base and Pd. A highly active, magnetically recoverable, recyclable catalyst for C–C cross-couplings at low Pd loadings". . p. 116 - 125. Retrieved 2018.
• 10、 Hajipour, Abdol R.,Abolfathi, Parisa. "Novel triazole-modified chitosan@nickel nanoparticles: efficient and recoverable catalysts for Suzuki reaction". . p. 2386 - 2391. Retrieved 2017.