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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

Quality Level

100

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

165.2 °F - closed cup

flash_point_c

74 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Toxic seizures in children: case scenarios and treatment strategies.
Michael Shannon et al.
Pediatric emergency care, 19(3), 206-210 (2003-06-19)
N-acyldihydropyridones as synthetic intermediates. A short synthesis of (?)-pumiliotoxin C.
Comins DL and Dehghani A.
Tetrahedron Letters, 32(41), 5697-5700 (1991)
Tetrahedron, 60, 4861-4861 (2004)
A highly stereocontrolled, four-step synthesis of (?)-lasubine II.
Brown JD, et al.
Journal of the American Chemical Society, 110(22), 7445-7447 (1988)
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)
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