4-tert-Butyl-1-methylpyridinium iodide

Base Information

• Chemical Name: 4-tert-Butyl-1-methylpyridinium iodide
• CAS No.: 64326-91-6
• Molecular Formula: C₁₀H₁₆N*I
• Molecular Weight: 277.148
• DSSTox Substance ID: DTXSID00982872
• Mol file: 64326-91-6.mol

Synonyms:4-tert-Butyl-1-methylpyridinium iodide;Pan-W-17;64326-91-6;Pyridinium, 4-tert-butyl-1-methyl-, iodide;N-Methyl-4-t-butylopyridine iodide [Polish];N-Methyl-4-t-butylopyridine iodide;Pyridinium, 4-(1,1-dimethylethyl)-1-methyl-, iodide;4-tert-butyl-1-methylpyridin-1-ium iodide;DTXSID00982872;LS-132294

Chemical Property of 4-tert-Butyl-1-methylpyridinium iodide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 277.03275
• Heavy Atom Count: 12
• Complexity: 115

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C1=CC=[N+](C=C1)C.[I-]

Technology Process of 4-tert-Butyl-1-methylpyridinium iodide

There total 1 articles about 4-tert-Butyl-1-methylpyridinium iodide 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: 85.0%

4-tert-butylpyridine (3978-81-2) + methyl iodide (74-88-4) → 4-(1,1-dimethylethyl)-1-methylpyridinium iodide (64326-91-6)

Guidance literature:

In acetonitrile; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.9b02694

Reference yield: 17.0%

4-tolyl iodide (624-31-7) + 4-(1,1-dimethylethyl)-1-methylpyridinium iodide (64326-91-6) → 4-(tert-butyl)-2-(p-tolyl)pyridine (1159004-34-8) + 4-(tert-butyl)-2,6-di-p-tolylpyridine

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; cetyltrimethylammonim bromide; potassium pivalate; triphenylphosphine; copper(I) bromide; In N,N-dimethyl acetamide; at 120 ℃; for 16h; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.9b02694

Reference yield:

4-(1,1-dimethylethyl)-1-methylpyridinium iodide (64326-91-6) → 6-tert-butyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine (102682-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) NaBH₄, 3.) H₃PO₄

2: 1.) trichloroethyl chloroformate, K₂CO₃, 2.) Zn / 1.) toluene, reflux, 72 h, 2.) acetic acid, RT, 4 h

3: 0.4 g / NaBH₄ / toluene / 3 h / Heating

With sodium tetrahydroborate; phosphoric acid; trichloroethyl chloroformate; potassium carbonate; zinc; In toluene;

DOI:10.1021/jm00159a038

upstream raw materials:

4-tert-butylpyridine

methyl iodide

Downstream raw materials:

4-tert-butyl-1-methyl-1,2,3,6-tetrahydro-pyridine

2-Benzyl-4-tert-butyl-1-methyl-1,2,3,6-tetrahydro-pyridine

6-Benzyl-4-tert-butyl-1-methyl-1,2,3,6-tetrahydro-pyridine

6-tert-butyl-3-(phenylacetyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine

Refernces

• 1、 Chen, Xue,Li, Wen-Jing,Li, Shun,Tang, Juan,Du, Xi,Zheng, Xue-Li,Yuan, Mao-Lin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua. "Palladium-Catalyzed Direct Arylation of Alkylpyridine via Activated N-Methylpyridinium Salts". . p. 622 - 632. Retrieved 2019/12/30.
• 2、 Jun, Daniel,Paar, Martin,Binder, Jiri,Marek, Jan,Pohanka, Miroslav,Stodulka, Petr,Kuca, Kamil. "Preparation and in vitro evaluation of monoquaternary inhibitors of brain cholinesterases". scheme or table. p. 500 - 503. Retrieved 2010/04/23.