ChemicalBook > CAS DataBase List > 2,6-Di-tert-butyl-4-methylpyridine

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

Product Name
2,6-Di-tert-butyl-4-methylpyridine
CAS No.
38222-83-2
Chemical Name
2,6-Di-tert-butyl-4-methylpyridine
Synonyms
DTBMP;Dibutylmethylpyridine;D2419;AB1003;AC-5133;AC1L40I3;Di-tert-butyl-4-Methylpyr;HVHZEKKZMFRULH-UHFFFAOYSA-N;2,6-Di-t-butyl-4-methylpyridine;2,6-Di-tert-butyl-4-methylpyridin
CBNumber
CB1165928
Molecular Formula
C14H23N
Formula Weight
205.34
MOL File
38222-83-2.mol
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2,6-Di-tert-butyl-4-methylpyridine Property

Melting point:
33-36 °C (lit.)
Boiling point:
233 °C (lit.)
Density 
1,476 g/cm3
refractive index 
n20/D 1.4763(lit.)
Flash point:
183 °F
storage temp. 
2-8°C
solubility 
ethanol: soluble5%, clear to slightly hazy, colorless to dark yellow
form 
Liquid or Low Melting Solid
pka
6.88±0.10(Predicted)
color 
brown
Water Solubility 
Sparingly soluble in water. Soluble in ethanol, acetic acid and diethyl ether.
Sensitive 
Air & Light Sensitive
BRN 
130503
InChIKey
HVHZEKKZMFRULH-UHFFFAOYSA-N
CAS DataBase Reference
38222-83-2(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
22-36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
F 
8-10-23
HS Code 
29333990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
249505
Product name
2,6-Di-tert-butyl-4-methylpyridine
Purity
98%
Packaging
5g
Price
$140
Updated
2024/03/01
Sigma-Aldrich
Product number
249505
Product name
2,6-Di-tert-butyl-4-methylpyridine
Purity
98%
Packaging
1g
Price
$46.7
Updated
2023/06/20
TCI Chemical
Product number
D2419
Product name
2,6-Di-tert-butyl-4-methylpyridine
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$131
Updated
2024/03/01
TCI Chemical
Product number
D2419
Product name
2,6-Di-tert-butyl-4-methylpyridine
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$437
Updated
2024/03/01
Alfa Aesar
Product number
L14143
Product name
2,6-Di-tert-butyl-4-methylpyridine, 97%
Packaging
1g
Price
$36.65
Updated
2024/03/01
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2,6-Di-tert-butyl-4-methylpyridine Chemical Properties,Usage,Production

Chemical Properties

light yellow powder

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.

Uses

2,6-Di-tert-butyl-4-methylpyridine has been used:

  • in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives
  • as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives
  • diastereoselective synthesis of β-thiomannopyranosides

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 3034, 1976 DOI: 10.1021/jo00880a027

General Description

2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base which distinguishes between protonic and Lewis acids. It also enables the direct high-yield conversion of aldehydes and ketones to vinyl triflates. It inhibits desilylation and hydration of the products during GaCl3-catalyzed ortho-ethynylation of phenol.

Purification Methods

A possible impurity is 2,6-di-tert-butyl-4-neopentylpyridine. Attempts to remove coloured impurities directly by distillation, acid-base extraction or treatment with activated charcoal were unsuccessful. Pure material is obtained by dissolving 0.3mole of the alkylpyridine in pentane (150mL) and introducing it at the top of a cold water jacketed chromatographic column (40 x 4.5cm) (cooling is necessary because the base in pentane reacts exothermically with alumina) containing activated and acidic alumina (300g). The column is eluted with pentane using a 1L constant pressure funnel fitted at the top of the column to provide slight pressure. All the pyridine is obtained in the first two litres of eluent (the progress of elution is monitored by spotting a fluorescent TLC plate and examining under short wave UV light—a dark blue spot is evidence for the presence of the alkylpyridine). Elution is complete in 1hour. Pentane is removed on a rotovap with 90-93% recovery yielding a liquid which solidifies on cooling, m 31-32o, and the base can be distilled. The HPtCl6 salt has m 213-314o(dec), and the CF3SO3H salt has m 202.5-203.5o (from CH2Cl2). [Anderson & Stang Org Synth Coll Vol VII 144 1981, Beilstein 20/6 V 190.]

2,6-Di-tert-butyl-4-methylpyridine Preparation Products And Raw materials

Raw materials

Methylpyran Pivaloyl chloride Trifluoromethanesulfonic acid

Preparation Products

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

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View Lastest Price from 2,6-Di-tert-butyl-4-methylpyridine manufacturers

Hebei Mojin Biotechnology Co., Ltd
Product
2,6-Di-tert-butyl-4-methylpyridine 38222-83-2
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-06-21
Suzhou Ryan Pharmachem Technology Co.,Ltd.
Product
2,6-Di-tert-butyl-4-methylpyridine 38222-83-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
kg grade
Release date
2023-05-08
Dideu Industries Group Limited
Product
2,6-Di-tert-butyl-4-methylpyridine 38222-83-2
Price
US $1.10/g
Min. Order
1g
Purity
99.00%
Supply Ability
100 Tons min
Release date
2021-08-25

38222-83-2, 2,6-Di-tert-butyl-4-methylpyridineRelated Search:

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  • 2,6-Di-tert-butyl-4-methylpyridine&gt
  • 2,6-Di-tert-butyl-4-methylpyridine ISO 9001：2015 REACH
  • AB1003
  • AC1L40I3
  • AC-5133
  • D2419
  • HVHZEKKZMFRULH-UHFFFAOYSA-N
  • 38222-83-2
  • 3822-83-2
  • C9 to C46
  • Building Blocks
  • Heterocyclic Building Blocks
  • Pyridines
  • Heterocycle-Pyridine series
  • C9 to C46
  • Heterocyclic Building Blocks
  • Pyridines
  • Pyridine series
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  • C13 to C40
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • 38222-83-2