2,6-Di-tert-butyl-4-methylpyridine

Base Information

• Chemical Name: 2,6-Di-tert-butyl-4-methylpyridine
• CAS No.: 38222-83-2
• Molecular Formula: C14H23N
• Molecular Weight: 205.343
• Hs Code.: 29333990
• European Community (EC) Number: 253-834-4
• NSC Number: 175792
• UNII: 83004E89V5
• DSSTox Substance ID: DTXSID10191615
• Nikkaji Number: J89.216E
• Wikidata: Q27269366
• Mol file: 38222-83-2.mol

Synonyms:2,6-Di-tert-butyl-4-methylpyridine;38222-83-2;2,6-ditert-butyl-4-methylpyridine;DTBMP;2,6-ditert-butyl-4-methyl-pyridine;Pyridine, 2,6-bis(1,1-dimethylethyl)-4-methyl-;2,6-di-t-Butyl-4-methylpyridine;MFCD00006305;2,6-di-tert-butyl-4-methyl-pyridine;2,6-di-tert-butyl-4-picoline;UNII-83004E89V5;EINECS 253-834-4;4-methyl-2,6-di-tert-butylpyridine;NSC-175792;83004E89V5;2,6-bis(1,1-dimethylethyl)-4-methylpyridine;NSC175792;SCHEMBL37832;DTXSID10191615;2,6-di-t-butyl 4-methylpyridine;2,6-di-tert-butyl-4methylpyridine;2,6-di-t- butyl-4-methylpyridine;2,6-di-t-butyl-4-methyl pyridine;2,6-di-t-butyl-4-methyl-pyridine;AMY15615;2,6-Di-tert-butil-4-metilpiridina;2,6-di-tert-butyl4-methyl-pyridine;2,6-di-tertbutyl-4-methyl-pyridine;AC1509;BBL102260;STL556059;2,6-di(tert-butyl)-4-methylpyridine;2,6-di-tert-butyl-4-methyl pyridine;AKOS015838101;AC-5133;CS-W007500;NSC 175792;SB52248;2,6-di-tert-butyl-(4-methylpyridine);SY005669;TS-00365;2,6-Di-tert-butyl-4-methylpyridine, 98%;C(C)(C)(C)c1cc(C)cc(n1)C(C)(C)C;D2419;FT-0639442;EN300-316978;2,6-DI-TERT-BUTYL-4-METHYLPYRIDINE [MI];A824064;AE-562/42754364;W-202564;Q27269366;IDINE, 2,6-BIS(1,1-DIMETHYLETHYL)-4-METHYL-

Chemical Property of 2,6-Di-tert-butyl-4-methylpyridine

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 0.0871mmHg at 25°C
• Melting Point: 33-36 °C(lit.)
• Refractive Index: n20/D 1.4763(lit.)
• Boiling Point: 233 °C at 760 mmHg
• PKA: 6.88±0.10(Predicted)
• Flash Point: 83.9 °C
• PSA: 12.89000
• Density: 0.883 g/cm³
• LogP: 3.98500
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: ethanol: soluble5%, clear to slightly hazy, colorless to dark ye
• Water Solubility.: Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 205.183049738
• Heavy Atom Count: 15
• Complexity: 184

Purity/Quality:

99% ^*data from raw suppliers

2,6-Di-tert-Butyl-4-methylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: CC1=CC(=NC(=C1)C(C)(C)C)C(C)(C)C
• Uses: 2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides. 2,6-Di-tert-butyl-4-methylpyridine has been used:in the synthesis of 1,2-dihydro-2-silanaphthalene derivativesas base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivativesdiastereoselective synthesis of β-thiomannopyranosides

Technology Process of 2,6-Di-tert-butyl-4-methylpyridine

There total 9 articles about 2,6-Di-tert-butyl-4-methylpyridine 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: 71.0%

methanol (67-56-1) + 2,6-di-tert-butyl-pyridine (585-48-8) → 2,6-di-tert-butyl-4-methylpyridine (38222-83-2)

Guidance literature:

With hydrogenchloride; 2,4-diphenylquinoline; In water; for 24h; Inert atmosphere; UV-irradiation;

DOI:10.1039/c7sc03768f

Reference yield: 30.0%

tert-butyl isocyanide (630-18-2) + Li2(TMM)(TMEDA)2 (41792-83-0) → 2,6-di-tert-butyl-4-methylpyridine (38222-83-2)

Guidance literature:

In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo01289a036

Reference yield:

2,6-di-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1392146-23-4) + methyl iodide (74-88-4) → 2,6-di-tert-butyl-4-methylpyridine (38222-83-2)

Guidance literature:

With C₂₁H₃₀ClNPPd; potassium tert-butylate; In tert-Amyl alcohol; at 65 ℃; for 18h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.9b00025

upstream raw materials:

tert-butyl isocyanide

Li₂(TMM)(TMEDA)2

tert-Amyl alcohol

2,2-dimethylpropanoic anhydride

Downstream raw materials:

dimethylphosphinic acid

4-[6-(4-methoxyphenyl)benzo[b]thiophen-3-yl]pyridine

(R)-N-(3,4-dimethoxybenzyl)-2-(2-methoxy-1-methylethylamino)-5-nitrobenzamide

Methyl 2-O-Benzyl-3-O-p-methoxybenzyl-6-O-methyl-α-D-glucopyranoside

Refernces

• 1、 McCallum,Pitre,Morin,Scaiano,Barriault. "The photochemical alkylation and reduction of heteroarenes". . p. 7412 - 7418. Retrieved 2017/10/31.
• 2、 Anderson, Albert G.,Stang, Peter J.. "2,6-DI-tert-butyl-4-methylpyridine". . p. 34 - 34. Retrieved 2017/05/17.