Merck
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L3900

Sigma-Aldrich

2,6-Lutidine

ReagentPlus®, 98%

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

product line

ReagentPlus®

assay

98%

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 for the oxidation of α-CF3 alcohols to the corresponding carbonyl compounds in the presence of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (Bobbitt′s salt) as oxidation reagent.
It can be used:
  • As a promoter for catalytic asymmetric fluorination of α-cyanophosphonates in the presence of chiral Pd(II)-bisphosphine complexes.
  • In combination with tert-butyldimethylsilyl triflate for the protection of tertiary alcohols and unreactive secondary alcohols.
  • In combination with triethylsilyl trifluoromethanesulfonate for the conversion of acetals to the corresponding aldehydes in dichloromethane followed by workup in water.

Packaging

100, 500 mL in glass bottle
2 L in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Unexpected Highly Chemoselective Deprotection of the Acetals from Aldehydes and Not Ketones: TESOTf? 2, 6-Lutidine Combination.
Fujioka H, et al.
Journal of the American Chemical Society, 126(38), 11800-11801 (2004)
Pd (II)-Catalyzed Asymmetric Fluorination of ?-Aryl-?-cyanophosphonates with the Aid of 2, 6-Lutidine.
Moriya K I, et al.
Synlett, 2007(07), 1139-1142 (2007)
Studies with trialkylsilyltriflates: new syntheses and applications.
Corey E J, et al.
Tetrahedron Letters, 22(36), 3455-3458 (1981)
Synthesis of 4-acetamido-2, 2, 6, 6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate and 4-acetamido-(2, 2, 6, 6-tetramethyl-piperidin-1-yl) oxyl and their use in oxidative reactions.
Mercadante M A, et al.
Nature Protocols, 8(4), 666-666 (2013)
Elisabetta Fanizza et al.
International journal of molecular sciences, 20(13) (2019-06-30)
The low photostability of conventional organic dyes and the toxicity of cadmium-based luminescent quantum dots have prompted the development of novel probes for in vitro and in vivo labelling. Here, a new fluorescent lanthanide probe based on silica nanoparticles is

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