L3900
2,6-Lutidine
ReagentPlus®, 98%
Synonym(s):
2,6-Dimethylpyridine
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About This Item
Empirical Formula (Hill Notation):
C7H9N
CAS Number:
Molecular Weight:
107.15
Beilstein:
105690
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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:
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.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary 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
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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)
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)
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)
Studies with trialkylsilyltriflates: new syntheses and applications.
Corey E J, et al.
Tetrahedron Letters, 22(36), 3455-3458 (1981)
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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