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
• General Description: 2,6-Di-tert-butyl-4-methylpyridine (DTBMP) is a sterically hindered, non-nucleophilic base used in organic synthesis to prevent unwanted side reactions, such as in the activation of amides or the formation of mixed acetals. It serves as an effective proton scavenger in reactions involving strong electrophiles or acidic conditions, ensuring high selectivity and yield, as demonstrated in the stereoselective synthesis of α-L-rhamnopyranosides and the reductive alkylation of lactams/amides. Its bulky tert-butyl groups hinder nucleophilic attack, making it particularly useful in reactions where traditional bases might interfere.

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:

1,2-bis<2-(2,6-di-t-butylpyridyl)ethyl>benzene

(2,6-di-tert-butyl-4-pyridyl)methylene bromide

2,2,2-trifluoro-N-(2-iodophenyl)acetamide

ethyl 4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate

Refernces

Stereoselective synthesis of β-L-rhamnopyranosides

10.1021/ja801574q

The study focuses on the stereoselective synthesis of α-L-Rhamnopyranosides (α-L-Rha), a challenging task due to their structural similarity to α-D-mannopyranosides. The researchers employed a novel intramolecular aglycon delivery (IAD) strategy using 2-naphthylmethyl (NAP) ether to create a temporary linkage between the donor and acceptor as a mixed acetal. This approach was found to be highly effective, yielding α-L-Rhamnosides with high selectivity and good yields. Chemicals used in the study include 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the formation of mixed acetals, MeOTf and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) for the IAD reaction, and TMS ether for intramolecular trapping of the benzylic cation. The purpose of these chemicals was to facilitate the synthesis of α-L-Rhamnosides with high stereoselectivity, which is crucial for the construction of complex carbohydrate structures found in various bacterial polysaccharides.

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

10.1002/chem.201002054

The research focuses on the development of a versatile one-pot reductive alkylation method for the transformation of lactams and amides into α-substituted amines, which are key structural features in many bioactive alkaloids and pharmaceutically relevant molecules. The study aimed to improve the efficiency of organic synthesis by utilizing a triflic anhydride (Tf2O)/2,6-di-tert-butyl-4-methylpyridine (DTBMP) combination as the amide activating system, Grignard reagents as alkylating agents, and lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4) as reducing agents. The methodology was demonstrated through the concise syntheses of bioactive alkaloids (-)-bgugaine, (-)-coniine, (+)-preussin, and (-)-cassine, showcasing the method's diastereoselectivity and versatility. The successful syntheses of these alkaloids not only highlight the efficiency of the developed method but also its potential for further application in the total synthesis of other alkaloids.

Synthesis of aromatic Amadori compounds

10.1016/0008-6215(91)84043-E

This research focuses on the synthesis of aromatic Amadori compounds, which are key intermediates in the Maillard reaction responsible for the aroma and color development in foods. The study involves the reaction of 2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-D-fructopyranose with alkyl esters of L-phenylalanine, L-tyrosine, and L-tryptophan to produce the Amadori compounds. The use of triflate as a highly reactive leaving group at C-1 of the sugar reagent significantly increases the yield of these compounds compared to traditional methods. The synthesis process also employs a sterically hindered, non-nucleophilic base, 2,6-di-tert-butyl-4-methylpyridine, to prevent unwanted side reactions. The resulting Amadori compounds are characterized using various spectroscopic techniques, including ‘H- and ‘3C-n.m.r. spectroscopy, i.r. spectroscopy, and mass spectroscopy. The study concludes that the synthetic approach used is more efficient and less time-consuming than the classical method of Amadori rearrangement via prolonged refluxing of D-glucose with amino acids.