Overview Reference
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2,6-DI-TERT-BUTYLPYRIDINE

Overview Reference
Product Name
2,6-DI-TERT-BUTYLPYRIDINE
CAS No.
585-48-8
Chemical Name
2,6-DI-TERT-BUTYLPYRIDINE
Synonyms
2,6-DI-T-BUTYLPYRIDINE;2,6-Bis(tert-butyl)pyridine;NSC 175805;2,6-DI-TERT-BUTYLPYRIDINE;Pyridine, 2,6-di-tert-butyl-;2,6-Di-tert-butylpyridine>2,6-DI-TERT-BUTYLPYRIDINE 97%;2,6-Di-tert-butylpyridine ,96%;2,6-DI-TERT-BUTYLPYRIDINE, >=97%;2,6-Di-tert-butylpyridine
CBNumber
CB6293437
Molecular Formula
C13H21N
Formula Weight
191.31
MOL File
585-48-8.mol
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2,6-DI-TERT-BUTYLPYRIDINE Property

Melting point:
2°C(lit.)
Boiling point:
100-101 °C/23 mmHg (lit.)
Density 
0.852 g/mL at 25 °C (lit.)
refractive index 
1.472-1.474
Flash point:
72 °C
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Liquid
pka
3.58(at 25℃)
Specific Gravity
0.852
color 
Clear yellow
Water Solubility 
Miscible with alcohol, acetone, and hexane. Immiscible with water.
Merck 
14,3036
BRN 
125886
Dielectric constant
3.3900000000000001
Stability:
Stable. Combustible. Incompatible with strong acids, strong oxidizing agents.
InChIKey
UWKQJZCTQGMHKD-UHFFFAOYSA-N
CAS DataBase Reference
585-48-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
36/37/38-22
Safety Statements 
37/39-26-36/37/39-36
RIDADR 
3267
WGK Germany 
3
Hazard Note 
Irritant
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

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.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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
219584
Product name
2,6-Di-tert-butylpyridine
Purity
≥97%
Packaging
1g
Price
$54.6
Updated
2024/03/01
Sigma-Aldrich
Product number
219584
Product name
2,6-Di-tert-butylpyridine
Purity
≥97%
Packaging
5g
Price
$193
Updated
2024/03/01
TCI Chemical
Product number
D1804
Product name
2,6-Di-tert-butylpyridine
Purity
>97.0%(GC)
Packaging
5g
Price
$142
Updated
2024/03/01
TCI Chemical
Product number
D1804
Product name
2,6-Di-tert-butylpyridine
Purity
>97.0%(GC)
Packaging
25g
Price
$489
Updated
2024/03/01
Alfa Aesar
Product number
H55761
Product name
2,6-Di-tert-butylpyridine, 97+%
Packaging
1g
Price
$42.65
Updated
2024/03/01
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2,6-DI-TERT-BUTYLPYRIDINE Chemical Properties,Usage,Production

Overview

2,6-Di-tert-butylpyridine is a weak base used in the preparation of 2, 6-di-tert-butylpyridine hydrotriflate. It is used as a proton scavenger to check the progress of the living polymerization of isobutylene. It is associated with cerric ammonium nitrate and used in the alfa-enolation of aldehydes. It is involved in the preparation of vinyl triflate using polymer-bound 2,6-di-tert-butylpyridine. Since it was first synthesized by Brown and Kanner[1], 2,6-di-tert-butylpyridine has attracted the interest of many researchers because of its unusually low basicity: with its two-alkyl substituents, DTBP is nevertheless a weaker base than unsubstituted pyridine in aqueous solution. Brown and Kanner[1] and others[2] proposed that the abnormally low basicity of DTBP was caused by steric hindrance to hydration of DTBPH+. Recent determinations of gas-phase proton affinities of DTBP and other alkyl-substituted pyridines showed that the basicity of DTBP in the gas phase was normal[2, 3], which confirmed that its weak basicity in water was due to solvent effects on DTBP and (or) DTBPH+. A complete analysis of the thermodynamic cycles linking the protonation processes of DTBP and other pyridines in the gas phase and in aqueous solution led Arnett and Chawla[2] to conclude that there was indeed some hindrance to the hydration of DTBPH+ as reflected in its abnormally low enthalpy of hydration. However, more recently Hopkins et al.[3], after investigating the protonation of additional tertbutylpyridines and repeating the thermodynamic determinations of Amett and Chawla[2] of DTBP, concluded from their new data that the hydration enthalpy of DTBPH+ was normal but that the corresponding entropy was abnormal; they suggested that the rotation of the water molecule attached to DTBPH+ and of -CMe3 was restricted. These results and conclusions were in agreement with the gas phase studies of Moet-Ner and Sieck[4] on the attachment of one water molecule to a series of pyridinium cations including DTBPH+.

Reference

  1. H. C. BROWN and B. KANNERJ. Am. Chem. Soc. 75, 3865 (1953).
  2. E. M. ARNETT and B. CHAWLAJ. Am. Chem. Soc. 101, 7141 (1979).
  3. H.P.HOPKINSD,.V.JAHAGIRDAP.RS,.MOULIKD,.H.AUE, H. M. WEBB,W. R. DAVIDSON and M. D. PEDLEY. J.. Am. Chem. Soc. 106,4341 (1984).
  4. M. MEOT-NEaRnd L. W. SIECK J. Am. Chem. Soc. 105, 2956 (1983) 

Chemical Properties

dark brown liquid

Uses

2,6-Di-tert-butylpyridine is used in the preparation of 2, 6-di-tert-butylpyridine hydrotriflate. It is used as a proton scavenger to check the progress of the living polymerization of isobutylene. It is associated with cerric ammonium nitrate and used in the alfa-enolation of aldehydes. It is involved in the preparation of vinyl triflate using polymer-bound 2,6-di-tert-butylpyridine.

Uses

2,6-Di-tert-butylpyridine was used as proton trapping agent to investigate the living polymerization of isobutylene. It was also used with cerric ammonium nitrate in the α-enolation of aldehydes leading to 1,4-dicarbonyl systems.

Definition

ChEBI: 2,6-di-tert-butylpyridine is a member of pyridines.

General Description

Reactivity of 2,6-di-tert-butylpyridine with iron(III) tetraphenylporphyrin pi-cation radical has been examined by proton NMR spectroscopy. Reaction of 2,6-di-tert-butylpyridine with methyl iodide and methyl fluorosulfonate under high pressure has been reported.

Purification Methods

Redistil it from KOH pellets. [Beilstein 20 III/IV 2868.]

2,6-DI-TERT-BUTYLPYRIDINE Preparation Products And Raw materials

Raw materials

Preparation Products

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2,6-DI-TERT-BUTYLPYRIDINE Suppliers

Auschemicals Pty Ltd
Tel
+61406202619
Email
info@auschemicals.com
Country
Australia
ProdList
426
Advantage
58
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View Lastest Price from 2,6-DI-TERT-BUTYLPYRIDINE manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
2,6-DI-TERT-BUTYLPYRIDINE 585-48-8
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-12-06
Hebei Mojin Biotechnology Co.,Ltd
Product
2,6-DI-TERT-BUTYLPYRIDINE 585-48-8
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
50000KG/month
Release date
2024-08-12
Suzhou Ryan Pharmachem Technology Co.,Ltd.
Product
2,6-DI-TERT-BUTYLPYRIDINE 585-48-8
Price
US $0.00-0.00/kg
Min. Order
10kg
Purity
98%
Supply Ability
hundred kgs grade
Release date
2023-05-08

585-48-8, 2,6-DI-TERT-BUTYLPYRIDINERelated Search:


  • Pyridine, 2,6-bis(1,1-dimethylethyl)-
  • Pyridine, 2,6-di-tert-butyl-
  • 2,6-DI-T-BUTYLPYRIDINE
  • 2,6-DI-TERT-BUTYLPYRIDINE
  • 2,6-Bis(1,1-dimethylethyl)pyridine
  • 2,6-Bis(tert-butyl)pyridine
  • 2,6-Di-tert-butylpyridine ,96%
  • 2,6-DI-TERT-BUTYLPYRIDINE 97%
  • 2,6-DI-TERT-BUTYLPYRIDINE, >=97%
  • 2,6-Di-tert-butylpyridine, 97% 25GR
  • 2,6-Di-tert-butylpyridine, 97% 5GR
  • NSC 175805
  • 2,6-Di-<i>tert</i>-butylpyridine
  • 2,6-Di-tert-butylpyridine, 96%, for synthesis
  • 2,6-Di-tert-butylpyridine&gt
  • 2,6-DI-TERT-BUTYLPYRIDINE ISO 9001:2015 REACH
  • CAS585-48-8 2,6-DI-TERT-BUTYLPYRIDINE
  • 585-48-8
  • C13H21N
  • Pyridines
  • Heterocyclic Building Blocks
  • Building Blocks
  • C9 to C46
  • Pyridines, Pyrimidines, Purines and Pteredines
  • Heterocyclic Compounds
  • C9 to C46
  • Heterocyclic Building Blocks
  • Pyridines