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336106

Sigma-Aldrich

2,6-Lutidine

Synonym(s):

2,6-Dimethylpyridine

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About This Item

Empirical Formula (Hill Notation):
C7H9N
CAS Number:
108-48-5
Molecular Weight:
107.15
Beilstein:
105690
EC Number:
203-587-3
MDL number:
MFCD00006345
UNSPSC Code:
12352005
PubChem Substance ID:
24860356
NACRES:
NA.22

form

liquid

Quality Level

300

refractive index

n20/D 1.497 (lit.)

bp

143-145 °C (lit.)

mp

−6 °C (lit.)

density

0.92 g/mL at 25 °C (lit.)

SMILES string

Cc1cccc(C)n1

InChI

1S/C7H9N/c1-6-4-3-5-7(2)8-6/h3-5H,1-2H3

InChI key

OISVCGZHLKNMSJ-UHFFFAOYSA-N

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General description

2,6-Lutidine, also known as 2,6-dimethylpyridine, is an organic compound that is commonly used as a reagent in various organic reactions, such as the synthesis of heterocycles, nitroalkenes, and alkyl halides. It can also be used as a catalyst in organic synthesis.

Application

2,6-Lutidine can be used as:
  • A base in the synthesis of an aldol adduct from malonic acid hemithioesters and aldehydes catalyzed by Cu(II) salt.
  • An additive in reductive cyclization of epoxygeranyl acetate.
  • A catalyst in combination with CuI for selective synthesis of N-sulfonyl-1,2,3-triazoles.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F

Flash Point(C)

32 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Cu (II)-catalyzed enantioselective aldol condensation between malonic acid hemithioesters and aldehydes.
Orlandi S, et al.
Tetrahedron Letters, 45(8), 1747-1749 (2004)
Ti (III)-catalyzed radical cyclization of 6, 7-epoxygeranyl acetate.
Fuse S, et al.
Tetrahedron Letters, 45(9), 1961-1963 (2004)
Copper-Catalyzed Synthesis of N-Sulfonyl-1, 2, 3-triazoles: Controlling Selectivity.
Yoo EJ, et al.
Angewandte Chemie (International Edition in English), 46(10), 1730-1733 (2007)
Kathryn A White et al.
Journal of colloid and interface science, 359(1), 126-135 (2011-04-22)
Using a system of modified silica particles and mixtures of water and 2,6-lutidine to form particle-stabilized emulsions, we show that subtle alterations to the hydration of the particle surface can cause major shifts in emulsion structure. We use fluorescence confocal
Wensheng Yu et al.
Organic letters, 6(19), 3217-3219 (2004-09-10)
[reaction: see text] Oxidative cleavage of olefins by OsO(4)-NaIO(4) sometimes suffers from low yields due to the formation of side products. It is found that the addition of 2,6-lutidine can suppress the side reactions and dramatically improve the yield of
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