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336106

Sigma-Aldrich

2,6-Lutidine

purified by redistillation, ≥99%

Synonym(s):
2,6-Dimethylpyridine
Empirical Formula (Hill Notation):
C7H9N
CAS Number:
Molecular Weight:
107.15
Beilstein:
105690
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥99%

purified by

redistillation

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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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.

Packaging

1, 2 L in Sure/Seal™
100 mL in Sure/Seal™
190 μL in ampule

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

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)

91.4 °F

Flash Point(C)

33 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
James R Frost et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(38), 13261-13277 (2015-08-01)
Since their isolation almost 20 years ago, the callipeltosides have been of long standing interest to the synthetic community owing to their unique structural features and inherent biological activity. Herein we present our full research effort that has led to the...
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)
Bojana Ginovska et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(44), 15713-15719 (2015-10-24)
We report that 2,6-lutidine⋅trichloroborane (Lut⋅BCl3 ) reacts with H2 in toluene, bromobenzene, dichloromethane, and Lut solvents producing the neutral hydride, Lut⋅BHCl2 . The mechanism was modeled with density functional theory, and energies of stationary states were calculated at the G3(MP2)B3...

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