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249505

Sigma-Aldrich

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

98%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C14H23N
Número de CAS:
38222-83-2
Peso molecular:
205.34
Beilstein/REAXYS Number:
130503
EC Number:
253-834-4
MDL number:
MFCD00006305
UNSPSC Code:
12352100
PubChem Substance ID:
24855001
NACRES:
NA.22

Quality Level

200

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

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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

Pictograms

Exclamation mark
GHS07

signalword

Warning

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_germany

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Organic Syntheses, 68, 138-138 (1990)
Hidekazu Arii et al.
Chemical communications (Cambridge, England), 50(50), 6649-6652 (2014-05-16)
Treatment of dialkylbenzylsilane (1) with trityl tetrakis(pentafluorophenyl)borate (TPFPB) in the presence of terminal or internal alkynes (3) and 2,6-di-tert-butyl-4-methylpyridine gave the corresponding 1,2-dihydro-2-silanaphthalene derivatives (4) in 34-82% yields.
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
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
Synthesis, 283-283 (1980)
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