3-Methyl-2-(p-tolyl)pyridine

Base Information

• Chemical Name: 3-Methyl-2-(p-tolyl)pyridine
• CAS No.: 64291-96-9
• Molecular Formula: C13H13 N
• Molecular Weight: 183.253
• European Community (EC) Number: 264-771-7
• DSSTox Substance ID: DTXSID30982845
• Nikkaji Number: J310.091J
• Wikidata: Q82969689
• Mol file: 64291-96-9.mol

Synonyms:3-Methyl-2-(p-tolyl)pyridine;64291-96-9;3-methyl-2-(4-methylphenyl)pyridine;EINECS 264-771-7;2-(4-methylphenyl)-3-methylpyridine;SCHEMBL2477267;DTXSID30982845;RYRDKQYQAMRCHF-UHFFFAOYSA-N

Chemical Property of 3-Methyl-2-(p-tolyl)pyridine

Chemical Property:

• Vapor Pressure: 0.00468mmHg at 25°C
• Boiling Point: 286°C at 760 mmHg
• Flash Point: 117.8°C
• PSA: 12.89000
• Density: 1.015g/cm³
• LogP: 3.36540
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 170

Purity/Quality:

99% purity ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=C(C=CC=N2)C

Technology Process of 3-Methyl-2-(p-tolyl)pyridine

There total 15 articles about 3-Methyl-2-(p-tolyl)pyridine 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%

2-bromo-3-picoline (3430-17-9) + 4-methylphenylboronic acid (5720-05-8) → 3-methyl-2-(4-methylphenyl)pyridine (64291-96-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In ethanol; water; toluene; for 24h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201612324

Reference yield: 97.0%

2-bromo-3-picoline (3430-17-9) + p-tolylboronic pinacol ester (195062-57-8) → 3-methyl-2-(4-methylphenyl)pyridine (64291-96-9)

Guidance literature:

With tricyclohexylphosphine-copper chloride; sodium t-butanolate; In toluene; at 100 ℃; for 15h; Inert atmosphere; Sealed tube;

DOI:10.1039/c8cc03145b

Reference yield: 86.0%

para-bromotoluene (106-38-7) + sodium 3-methylpyridine-2-sulfinate → 3-methyl-2-(4-methylphenyl)pyridine (64291-96-9)

Guidance literature:

With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; potassium carbonate; In 1,4-dioxane; at 100 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b02944

upstream raw materials:

5-bromo-5-methyl-6-(4-methylphenyl)-2,3,4,5-tetrahydropyridine

2-bromo-3-picoline

4-methylphenylboronic acid

6-azido-3-bromo-3-methyl-1-(4-methylphenyl)-2-hexanone

Downstream raw materials:

2-(2-chloro-4-methylphenyl)-3-methylpyridine

2-(2-iodo-4-methylphenyl)-3-methylpyridine

Refernces

• 1、 Chen, Hua,Haiyan, Fu,Jiang, Weidong,Li, Ruixiang,Li, Shun,Li, Wenjing,Tang, Juan,Xu, Bin,Yuan, Maolin,Zheng, Xueli. "Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes". supporting information. p. 7814 - 7819. Retrieved 2020/11/03.
• 2、 Yang, Qi-Liang,Li, Chuan-Zeng,Zhang, Liang-Wei,Li, Yu-Yan,Tong, Xiaofeng,Wu, Xin-Yan,Mei, Tian-Sheng. "Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes". supporting information. p. 1208 - 1212. Retrieved 2018/10/20.