3,5-Dimethyl-1,1'-biphenyl

Base Information

• Chemical Name: 3,5-Dimethyl-1,1'-biphenyl
• CAS No.: 17057-88-4
• Molecular Formula: C14H14
• Molecular Weight: 182.265
• Hs Code.: 2902909090
• European Community (EC) Number: 241-120-5
• UNII: WJ1G5X2V0V
• DSSTox Substance ID: DTXSID70168883
• Nikkaji Number: J318.337H
• Wikidata: Q83038496
• ChEMBL ID: CHEMBL464380
• Mol file: 17057-88-4.mol

Synonyms:3,5-Dimethyl-1,1'-biphenyl;3,5-dimethylbiphenyl;17057-88-4;3,5-Dimethyl-biphenyl;1,3-dimethyl-5-phenylbenzene;1,1'-Biphenyl, 3,5-dimethyl-;EINECS 241-120-5;Biphenyl, 3,5-dimethyl-;WJ1G5X2V0V;UNII-WJ1G5X2V0V;CHEMBL464380;3,5-Dimethyl-1,1/'-biphenyl;DTXSID70168883;MFCD09031096;AKOS006289821;AC-18801;E90183

Chemical Property of 3,5-Dimethyl-1,1'-biphenyl

Chemical Property:

• Melting Point: 22.5°C
• Refractive Index: 1.5952
• Boiling Point: 274.5°Cat760mmHg
• Flash Point: 121.6°C
• PSA: 0.00000
• Density: 0.973g/cm³
• LogP: 3.97040
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 182.109550447
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

98%Min ^*data from raw suppliers

3,5-Dimethyl-biphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)C2=CC=CC=C2)C
• Uses: 3,5-Dimethyl-biphenyl is a useful reagent for organic synthesis. It is used in the preparation of orthopalladated complexes with multidentated ligands as catalyst for Suzuki and heck reactions.

Technology Process of 3,5-Dimethyl-1,1'-biphenyl

There total 94 articles about 3,5-Dimethyl-1,1'-biphenyl 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%

5-bromo-1,3-xylene (556-96-7) + phenylboronic acid (98-80-6) → 3,5-dimethylbiphenyl (17057-88-4)

Guidance literature:

With potassium phosphate; 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride; bis(η3-allyl-μ-chloropalladium(II)); In 1,4-dioxane; at 80 ℃; for 12h;

DOI:10.1002/adsc.200404015

Reference yield: 100.0%

5-bromo-1,3-xylene (556-96-7) + tributylphenylstannane (960-16-7) → 3,5-dimethylbiphenyl (17057-88-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate; In 1,4-dioxane; at 100 ℃; for 20h;

DOI:10.1021/jo048066q

Reference yield: 99.0%

1-chloro-3,5-dimethylbenzene (556-97-8) → 3,5-dimethylbiphenyl (17057-88-4) + phenylboronic acid (98-80-6)

Guidance literature:

With cesium fluoride; Pd(dba)2; In toluene;

upstream raw materials:

1-Phenyl-3,5-dimethyl-cyclohexen-1

1,3-dimethyl-5-cyclohexylbenzene

2,4,6-trimethylpyrylium chlorate(VII)

cis-3,5-Dimethylbi-1-cyclohexen-1-yl

Downstream raw materials:

(2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)chloromethane

(2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)methanol

{(2,6-bibromo-4-phenyl)phenyl}{(2,6-dimethyl-4-phenyl)phenyl}ketone

(2,6-dibromo-4-phenylphenyl)(2,6-dimethyl-4-phenylphenyl)diazomethane

Refernces

• 1、 Sun, Yue,Yan, Meng-Qi,Liu, Yan,Lian, Ze-Yu,Meng, Tong,Liu, Sheng-Hua,Chen, Jian,Yu, Guang-Ao. "Phenylphosphinacalix[3]trifuran: Synthesis, coordination and application in the Suzuki-Miyaura cross-coupling reaction in water". . p. 71437 - 71440. Retrieved 2015.
• 2、 Bei, Xiaohong,Turner, Howard W.,Weinberg, W. Henry,Guram, Anil S.,Petersen, Jeffrey L.. "Palladium/P,O-Ligand-Catalyzed Suzuki Cross-Coupling Reactions of Arylboronic Acids and Aryl Chlorides. Isolation and Structural Characterization of (P,O)-Pd(dba) Complex". . p. 6797 - 6803. Retrieved 1999.
• 3、 Deschamps, Bernard,Le Goff, Xavier,Ricard, Louis,Le Floch, Pascal. "Phosphaalkenes palladium(II) complexes in the Suzuki and Sonogashira cross-coupling reactions". . p. 363 - 371. Retrieved 2007.
• 4、 Sarkar, Bibhas R.,Chaudhari, Raghunath V.. "Ossification: A new approach to immobilize metal complex catalysts-applications to carbonylation and Suzuki coupling reactions". . p. 231 - 238. Retrieved 2006.
• 5、 Yang, Pengbo,Ma, Rong,Bian, Fengling. "Palladium Supported on Metformin-Functionalized Magnetic Polymer Nanocomposites: A Highly Efficient and Reusable Catalyst for the Suzuki–Miyaura Coupling Reaction". . p. 3746 - 3754. Retrieved 2016.
• 6、 Fouquet, Eric,Rodriguez, Alain L.. "Activated monoorganotins for the modified stille coupling reaction with triflates". . p. 1323 - 1324. Retrieved 1998.
• 7、 Fu, Yu-Fang,Song, Kun-Peng,Zou, Zhi-Juan,Li, Ming-Qi. "External cross-linked sulfonate-functionalized N-heterocyclic carbenes: an efficient and recyclable catalyst for Suzuki–Miyaura reactions in water". . p. 665 - 672. Retrieved 2018.
• 8、 Fuchibe, Kohei,Ohshima, Yoshitaka,Mitomi, Ken,Akiyama, Takahiko. "Low-valent niobium-catalyzed reduction of α,α,α- trifluorotoluenes". . p. 1497 - 1499. Retrieved 2007.
• 9、 Huang, Wei,Jiang, Jun,Wu, Dayu,Xu, Jun,Xue, Bing,Kirillov, Alexander M.. "A Highly Stable Nanotubular MOF Rotator for Selective Adsorption of Benzene and Separation of Xylene Isomers". . p. 10524 - 10526. Retrieved 2015.
• 10、 Lee, Woong-Sup,Byun, Sangmoon,Kwon, Jungmin,Kim, B. Moon. "Magnetic Pd–Fe3O4 Heterodimer Nanocrystals as Recoverable Catalysts for Ligand-Free Hiyama Cross-Coupling Reactions". . p. 1992 - 1997. Retrieved 2016.