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460621

Sigma-Aldrich

4-Methoxypyridine

97%

Synonym(s):

γ-Methoxypyridine

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About This Item

Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
620-08-6
Molecular Weight:
109.13
EC Number:
210-624-7
MDL number:
MFCD00674049
UNSPSC Code:
12352100
PubChem Substance ID:
24869720
NACRES:
NA.22

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

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.

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

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
A highly stereocontrolled, four-step synthesis of (?)-lasubine II.
Brown JD, et al.
Journal of the American Chemical Society, 110(22), 7445-7447 (1988)
Tetrahedron, 60, 4861-4861 (2004)
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