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144428

Sigma-Aldrich

2,6-Lutidine-α2,3-diol

99%

Synonym(s):

3-Hydroxy-6-methyl-2-pyridinemethanol

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About This Item

Empirical Formula (Hill Notation):
C7H9NO2
CAS Number:
42097-42-7
Molecular Weight:
139.15
EC Number:
255-657-8
MDL number:
MFCD00006350
UNSPSC Code:
12352100
PubChem Substance ID:
24848652
NACRES:
NA.22

Assay

99%

form

powder

mp

157-159 °C (lit.)

SMILES string

Cc1ccc(O)c(CO)n1

InChI

1S/C7H9NO2/c1-5-2-3-7(10)6(4-9)8-5/h2-3,9-10H,4H2,1H3

InChI key

PAGTXDLKXRBHFL-UHFFFAOYSA-N

General description

2,6-Lutidine-α2,3-diol (3-Hydroxy-6-methyl-2-pyridinemethanol) on condensation with chlorides of carbamidophosphoric acids yields N-Substituted N′-[6-methyl-2-oxido-1,3,2-dioxaphosphinino(5,4,-b)pyridine-2-yl]urea. It forms organotin (IV) complexes on reaction with dimethyl-, diethyl- and dibutyltin (IV) oxide.

Application

2,6-Lutidine-α2,3-diol (3-Hydroxy-6-methyl-2-pyridinemethanol) was used in the synthesis of:
  • (3-hydroxy-6-methylpyridin-2-yl)methyl pivaloate
  • triflate
  • (3-(allyloxy)-6-methylpyridin-2-yl)methanol

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis, structure and cytotoxicity of diorganotin (IV) complexes of 2, 6-lutidine-a2, 3-diol (Lu): The crystal structures of Lu and [SnMe2 (H2O)(Lu-2H)].
Casas JS, et al.
Journal of Organometallic Chemistry, 692(16), 3547-3554 (2007)
Synthesis and antimicrobial activity of N-substituted N'-[6-methyl-2-oxido-1, 3, 2-dioxaphosphinino (5, 4-b) pyridine-2-yl] ureas.
Reddy PC, et al.
Heteroatom Chem., 14(6), 509-512 (2003)
James R Vyvyan et al.
Synthesis, 2010(21), 3637-3644 (2011-04-26)
Palladium-catalyzed Suzuki-type couplings of 3-pyridyl triflates with alkenyl pinacol boronates proceed in good to excellent yield. Optimized conditions use Pd(PPh(3))(4) (10 mol %) as catalyst with K(3)PO(4) (3 equiv) as base in dioxane.

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