460621
4-Methoxypyridine
97%
Synonym(s):
γ-Methoxypyridine
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About This Item
Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
Molecular Weight:
109.13
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
97%
refractive index
n20/D 1.516 (lit.)
bp
108-111 °C/65 mmHg (lit.)
density
1.075 g/mL at 25 °C (lit.)
SMILES string
COc1ccncc1
InChI
1S/C6H7NO/c1-8-6-2-4-7-5-3-6/h2-5H,1H3
InChI key
XQABVLBGNWBWIV-UHFFFAOYSA-N
Related Categories
General description
4-Methoxypyridine has been prepared from 4-methoxypyridine-N-oxide, via catalytic hydrogenation. Ortho lithiation of 4-methoxypyridine using mesityllithium as the metalating base has been studied.
Application
4-Methoxypyridine was used as a starting reagent for the stereocontrolled synthesis of (±)-pumiliotoxin C and (±)-lasubine II. It was also used in an efficient construction of dihyropyridin-4-ones, which serves as potential ligands for neuronal nicotinic acetycholine receptors.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
165.2 °F
Flash Point(C)
74 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Woldman YaYu et al.
FEBS letters, 212(1), 53-57 (1987-02-09)
Longitudinal relaxation (T1) measurements for all lines (alpha-CH, beta-CH, O-CH3) in the 4-methoxypyridine 1H-NMR spectrum were used to study the interaction of 4-methoxypyridine with purified microsomal cytochrome P-450 from livers of phenobarbital-treated rats. The paramagnetic contribution to the observed T1(-1)
Addition of Grignard reagents to 1-acyl-4-methoxypyridinum salts. An approach to the synthesis of quinolizidinones.
Connns DL and Brown JD.
Tetrahedron Letters, 27(38), 4549-4552 (1986)
A highly stereocontrolled, four-step synthesis of (?)-lasubine II.
Brown JD, et al.
Journal of the American Chemical Society, 110(22), 7445-7447 (1988)
Iu Iu Vol'dman et al.
Bioorganicheskaia khimiia, 15(8), 1044-1055 (1989-08-01)
Acceleration of substrate longitudinal relaxation (T1) was used to study cytochrome P-450-aminopyrine (1st type substrate) and P-450-4-methoxypyridine (2nd type substrate) complexes. Dissociation constant, T1 and/or residence time of substrate in the complex can be obtained from the dependence of T1
Tetrahedron, 60, 4861-4861 (2004)
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