2-Chloro-4-methoxypyridine Chemical Properties

Boiling point:

224-225 °C (lit.)

Density 

1.258 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5400(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in alcohol.

form 

Liquid

pka

2.25±0.10(Predicted)

Specific Gravity

1.258

color 

Colorless to pale yellow

BRN 

1423379

InChI

InChI=1S/C6H6ClNO/c1-9-5-2-3-8-6(7)4-5/h2-4H,1H3

InChIKey

PMTPFBWHUOWTNN-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(OC)=C1

CAS DataBase Reference

17228-69-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37

RIDADR 

2810

WGK Germany 

3

PackingGroup 

III

HS Code 

29333990

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-4-methoxypyridine Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

It is an active pharmaceutical ingredient.

Uses

2-Chloro-4-methoxypyridine may be used to synthesize:

• 2-(2′,4′-difluorophenyl)-4-methoxypyridine
• (2-chloro-4-methoxypyridin-3-yl)bis-[2-(methylsulfanyl)pyrimidin-4-yl]methanol
• (2-chloro-4-methoxypyridin-3-yl)bis-[2-(methylsulfanyl) pyrimidin-4-yl]methyl acetate

General Description

2-Chloro-4-methoxypyridine can be obtained from the reaction between 2-chloro-4-nitropyridine and sodium methoxide in the presence of dioxane. It can also be prepared starting from 4-methoxy-2(1H)-pyridone and 4-nitropyridine N-oxide.

Synthesis

At room temperature, 4-tert-butylpyridine (5.5 mL, 5.08 g, 37.5 mmol, Aldrich) was dissolved in acetic acid (30 ) mL, Fluka). Hydrogen peroxide was added (30% aqueous solution, 11.5 mL, containing 3.83 g H2O2, 113 mmol, excess, Fluka.). The reaction mixture was stirred at 80 ??C overnight. It was rotor evaporated to 1/3 of its volume, neutralized with aqueous Na2CO3 and extracted several times with CH2Cl2. The organic layer was evaporated to dryness. The starting material (0.2-1.0% CH3OH in CH2Cl2) was removed and the product (5-7% CH3OH in CH2Cl) was recovered by chromatographic purification (run twice; silica, 2 x 25 g). 2-chloro-4-methoxypyridine. The reaction was carried out in dry DMF under argon. At room temperature, sodium methanol (190) was added to the reaction. mg, 3.52 mmol, excess, Fluka) was added to 2-chloro-4-nitropyridine (500 mg, 3.15 mmol, Aldrich) in DMF immediately undergoes an exothermic reaction and the color of the mixture changes from light yellow to dark red. Stirring for 3 h at room temperature gave a brown suspension which was extracted with water and ether. The organic layer was washed with water to remove the DMF. purification by chromatography (silica, 10 g; CH2Cl2) afforded the colorless oily product 2-chloro-4-methoxypyridine: 393 mg (2.74 mmol, 87%).

2-Chloro-4-methoxypyridine(17228-69-2)Related Product Information

• 4-Methoxypyridine
• 2-Chloro-5-chloromethylpyridine
• 2-Chloro-4-picoline
• Clopidol
• 4-Methoxybenzylchloride
• 2-CHLORO-4-METHOXYPYRIMIDINE
• 2-CHLORO-4-METHOXYNICOTINONITRILE
• 2-CHLORO-6-METHOXYPYRIDINE,6-Chloro-2-methoxypyridine,2-Chloro-6-methoxypyridine, GC 98%
• Difluorochloromethane
• 2-CHLORO-4-METHOXY-3-NITROPYRIDINE
• 2-CHLORO-3,5-DIMETHYL-4-METHOXY PYRIDINE HYDROCHLORIDE
• 6-CHLORO-4-ETHOXYNICOTINIC ACID
• 3-Chloro-2-methoxypyridine 98%,3-CHLORO-2-METHOXYPYRIDINE
• 5-CHLORO-2-METHOXYPYRIDINE
• 2-Chloro-3-methoxypyridine ,98%,2-CHLORO-3-METHOXYPYRIDINE
• 3-Bromo-2-methoxy-5-trifluoromethylpyridine
• 3-CHLORO-2-METHOXYPYRIDINE-5-BORONIC ACID
• 2-Chloro-5-methoxypyridine-3-boronic acid,2-Chloro-5-methoxypyridine-4-boronic acid,2-Chloro-4-methoxypyridine-3-boronic acid