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219584

Sigma-Aldrich

2,6-Di-tert-butylpyridine

≥97%

Synonym(s):

2,6-Bis(1,1-dimethylethyl)pyridine, 2,6-Ditert-butylpyridine

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About This Item

Empirical Formula (Hill Notation):
C13H21N
CAS Number:
585-48-8
Molecular Weight:
191.31
Beilstein:
125886
EC Number:
209-557-6
MDL number:
MFCD00006306
UNSPSC Code:
12352100
PubChem Substance ID:
24853137
NACRES:
NA.22

Assay

≥97%

form

liquid

refractive index

n20/D 1.473 (lit.)

bp

100-101 °C/23 mmHg (lit.)

density

0.852 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(C)c1cccc(n1)C(C)(C)C

InChI

1S/C13H21N/c1-12(2,3)10-8-7-9-11(14-10)13(4,5)6/h7-9H,1-6H3

InChI key

UWKQJZCTQGMHKD-UHFFFAOYSA-N

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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.

Application

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

159.8 °F - closed cup

Flash Point(C)

71 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Karolina A Tarach et al.
ChemSusChem, 12(3), 633-638 (2018-12-07)
A new theoretical and practical framework has been developed through operando study of the zeolite catalytic cracking of low-density polyethylene (as a model reaction) under reaction conditions. Results show that microporous ZSM-5 gives rise to less cracking products. Hierarchical ZSM-5
Reactions of crowded molecules under high pressure. Reactions of 2, 6-di-tert-butylpyridine with methyl iodide and methyl fluorosulfonate under high pressure.
Okamoto Y and Lee KI.
Journal of the American Chemical Society, 97(!4), 4015-4018 (1975)
Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.
Hye-Young Jang et al.
Journal of the American Chemical Society, 129(22), 7004-7005 (2007-05-15)
Living carbocationic polymerization of isobutylene with blocked bifunctional initiators in the presence of di-tert-butylpyridine as a proton trap.
Gyor M, et al.
J. Macromol. Sci., Pure Appl. Chem., 29(8), 639-653 (1992)
Krystyna Rachlewicz et al.
Inorganic chemistry, 35(5), 1136-1147 (1996-02-28)
The reactivity of iron(III) tetraphenylporphyrin pi-cation radical (TPP(*))Fe(III)(ClO(4))(2), (1-1) iron(III) tetra-p-tolylporphyrin pi-cation radical (TTP(*))Fe(III)(ClO(4))(2) (1-2) and iron(III) tetramesitylporphyrin pi-cation radical (TMP(*))Fe(III)(ClO(4))(2) (1-3) complexes with 2,4,6-collidine, 2,3,6-collidine, 2-picoline, 2,6-di-tert-butylpyridine, and 2,6-dibromopyridine has been examined by (1)H NMR spectroscopy in dichloromethane-d(2) solution
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