2-Chloro-4-picoline Chemical Properties

Melting point:

115°C

Boiling point:

194-195 °C (lit.)

Density 

1.142 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.529(lit.)

Flash point:

193 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

0.94±0.10(Predicted)

Specific Gravity

1.14

color 

Clear colorless to light yellow

InChI

InChI=1S/C6H6ClN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3

InChIKey

MZVSTDHRRYQFGI-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(C)=C1

CAS DataBase Reference

3678-62-4(CAS DataBase Reference)

NIST Chemistry Reference

2-Cl-4-(CH3)-pyridine(3678-62-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29349990

MSDS

• Language:English Provider:2-Chloro-4-methylpyridine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-Chloro-4-picoline Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid.

Uses

2-Chloro-4-methylpyridine is used as a reagent in the synthesis of the mGLUR5 modulators imidazolyl-ethynyl-pyridines as potential antipsychotics. It is also used in the preparation of trifluoromethyl(pyrimidinyl)azetidinecarboxamides as potent, orally bioavailable TGR5 agonists.

General Description

2-Chloro-4-methylpyridine (2-Chloro-4-picoline) reacts with 3,5-bis(trifluoromethyl)phenylboronic acid to form 2-(3,5-bis(trifluoromethyl)phenyl)-4-methylpyridine by palladium-catalyzed cross-coupling reaction.

Synthesis

a) Sodium nitrite (13.88 g, 200 mmol) was slowly added to a concentrated hydrochloric acid (200 mL) solution of 2-amino-4-methylpyridine (15.0 g, 139 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was poured into ice (500 g). The pH of the mixture was adjusted using concentrated ammonia to 8.0. Subsequently, the mixture was extracted with ether (3 x 300 mL). The combined ether layers were washed sequentially with deionized water (2 × 200 mL) and saturated brine (200 mL). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-chloro-4-methylpyridine (10.3 g, 58% yield) as a pale yellow oil. Mass spectrum (electrospray ionization) m/e 127.8 (M + H)+.

References

[1] Patent: US2002/91264, 2002, A1
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
[3] Acta Chemica Scandinavica, 1992, vol. 46, # 2, p. 157 - 162
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
[5] Patent: CN107151229, 2017, A. Location in patent: Paragraph 0023; 0027

2-Chloro-4-picoline(3678-62-4)Related Product Information

• 2-Chloro-5-chloromethylpyridine
• Clopidol
• 2,6-Lutidine
• Pentachloropyridine
• Epichlorohydrin
• 2-Chloro-3-cyanopyridine
• 2-Chloro-4-nitropyridine
• 2-(Chloromethyl)pyridine
• 4-Methylpyridine
• Azamethiphos
• 2,4,6-Collidine
• Chloroacetic acid
• 2-Chloro-4-(trifluoromethyl)pyridine
• 2,6-Dichloro-4-(trifluoromethyl)pyridine
• ETHYL 2-CHLORO-3-CYANO-6-METHYLISONICOTINATE
• METHYL 2,6-DICHLOROISONICOTINATE
• 2-CHLOROLEPIDINE
• 2-Chloro-4-methyl-3-nitropyridine