249505
2,6-Di-tert-butyl-4-methylpyridine
98%
Synonym(s):
2,6-Bis(1,1-dimethylethyl)-4-methylpyridine, 2,6-Bis(tert-butyl)-4-methylpyridine, 2,6-Ditert-butyl-4-methylpyridine, 4-Methyl-2,6-di-tert-butylpyridine
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About This Item
Empirical Formula (Hill Notation):
C14H23N
CAS Number:
Molecular Weight:
205.34
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
253-834-4
Beilstein/REAXYS Number:
130503
MDL number:
Assay:
98%
Form:
solid
Quality Level
assay
98%
form
solid
refractive index
n20/D 1.4763 (lit.)
bp
233 °C (lit.)
mp
33-36 °C (lit.)
solubility
ethanol: soluble 5%, clear to slightly hazy, colorless to dark yellow
storage temp.
2-8°C
SMILES string
Cc1cc(nc(c1)C(C)(C)C)C(C)(C)C
InChI
1S/C14H23N/c1-10-8-11(13(2,3)4)15-12(9-10)14(5,6)7/h8-9H,1-7H3
InChI key
HVHZEKKZMFRULH-UHFFFAOYSA-N
General description
2,6-Di-tert-butyl-4-methylpyridine is a sterically hindered, non-nucleophilic base which distinguishes between BrÖnsted (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.
Application
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
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
183.2 °F - closed cup
flash_point_c
84 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Katsumi Kobayashi et al.
Journal of the American Chemical Society, 124(29), 8528-8529 (2002-07-18)
Phenols are ethynylated at the ortho position with silylated chloroethyne in the presence of a catalytic amount of GaCl3 and lithium phenoxide. The lithium salt is essential for the catalysis, and addition of 2,6-di(tert-butyl)-4-methylpyridine inhibits desilylation and hydration of the
D Crich et al.
The Journal of organic chemistry, 65(3), 801-805 (2000-05-18)
A highly diastereoselective synthesis of beta-thiomannopyranosides is described in which S-phenyl 2,3-di-O-benzyl-4, 6-O-benzylidene-1-deoxy-1-thia-alpha-D-mannopyranoside S-oxide is treated with triflic anhydride and 2, 6-di-tert-butyl-4-methylpyridine in CH(2)Cl(2) at -78 degrees C leading to the formation of an intermediate alpha-mannosyl triflate. Addition of primary
Synthesis, 283-283 (1980)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 249505-25G | 04061833070819 |
| 249505-5G | 04061825928630 |
| 249505-1G | 04061825928623 |