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2-Chloro-4-picoline

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CAS:3678-62-4
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2-Chloro-4-picoline Basic information
Product Name:2-Chloro-4-picoline
Synonyms:2-Chlor-4-methylpyridin;2-Chlor2-Chloro-4-picolineo-4-picoline;2-Chloro-4-mehyl pyridine;4-Picoline, 2-chloro-;Pyridine, 2-chloro-4-methyl-;2-CHLORO-GAMMA-PICOLINE;2-CHLOROPICOLINE;2-CHLORO-4-PICOLINE
CAS:3678-62-4
MF:C6H6ClN
MW:127.57
EINECS:222-951-2
Product Categories:Pyridine;pyridine derivative;pyridine series;Chloropyridines;Halopyridines;Halides;Pyridines
Mol File:3678-62-4.mol
2-Chloro-4-picoline Structure
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.)
Fp 193 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
form Liquid
pka0.94±0.10(Predicted)
Specific Gravity1.14
color Clear colorless to light yellow
InChIInChI=1S/C6H6ClN/c1-5-2-3-8-6(7)4-5/h2-4H,1H3
InChIKeyMZVSTDHRRYQFGI-UHFFFAOYSA-N
SMILESC1(Cl)=NC=CC(C)=C1
CAS DataBase Reference3678-62-4(CAS DataBase Reference)
NIST Chemistry Reference2-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 Information
ProviderLanguage
2-Chloro-4-methylpyridine English
ACROS English
SigmaAldrich English
2-Chloro-4-picoline Usage And Synthesis
Chemical PropertiesColorless to light yellow liquid.
Uses2-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 Description2-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
4-Methylpyridin-2-amine

695-34-1

2-Chloro-4-picoline

3678-62-4

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