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108596

Sigma-Aldrich

3-Chloro-6-methoxypyridazine

95%

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Empirical Formula (Hill Notation):
C5H5ClN2O
CAS Number:
1722-10-7
Molecular Weight:
144.56
EC Number:
217-019-7
MDL number:
MFCD00006467
UNSPSC Code:
12352100
PubChem Substance ID:
24846813
NACRES:
NA.22

Assay

95%

mp

84-85 °C (lit.)

SMILES string

COc1ccc(Cl)nn1

InChI

1S/C5H5ClN2O/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3

InChI key

XBJLKXOOHLLTPG-UHFFFAOYSA-N

General description

3-Chloro-6-methoxypyridazine undergoes regioselective metallation using various lithium alkylamides, temperatures and solvents (THF and ether). It was lithiated using lithium 2,2,6,6-tetramethylpiperidide during the synthesis of minaprine.

Application

3-Chloro-6-methoxypyridazine was used in the preparation of number of α-aryl-α-(pyridazin-3-yl)-acetonitriles.

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Advances in the directed metallation of azines and diazines (pyridines, pyrimidines, pyrazines, pyridazines, quinolines, benzodiazines and carbolines). Part 2: Metallation of pyrimidines, pyrazines, pyridazines and benzodiazines.
Turck A, et al.
Tetrahedron, 57(21), 4489-4505 (2001)
Franciszek Herold et al.
Molecules (Basel, Switzerland), 12(12), 2643-2657 (2008-02-09)
This paper describes a modified method of preparation of a number of alpha-aryl-alpha-(pyridazin-3-yl)-acetonitriles via the C-arylation reaction of the corresponding carbanionsof phenylacetonitriles using 3-chloropyridazine derivatives. KOH and DMSO were used inthe deprotonation process, which made the reaction very simple and

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