| Identification | More | [Name]
2-Chloro-4-picoline | [CAS]
3678-62-4 | [Synonyms]
2-CHLORO-4-METHYLPYRIDINE
2-CHLORO-4-PICOLINE
2-CHLORO-GAMMA-PICOLINE
2-CHLOROPICOLINE
4-Picoline, 2-chloro-
Pyridine, 2-chloro-4-methyl-
2-chloro-4-methylpyrdine
2-Chloro-4-methylpyridine(2-Chloropicoline)
2-CHLORO-4-PICOLINE 2-CHLORO-4-METHYLPYRIDINE
2-CHLORO-4-METHYLPYRIDINE (2-CHLORO-4-PICOLINE)
HCPY1902-Chloro-4-picoline | [EINECS(EC#)]
222-951-2 | [Molecular Formula]
C6H6ClN | [MDL Number]
MFCD00023418 | [Molecular Weight]
127.57 | [MOL File]
3678-62-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liquid. | [Melting point ]
115°C | [Boiling point ]
194-195 °C (lit.) | [density ]
1.456 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 | [pka]
0.94±0.10(Predicted) | [color ]
Clear colorless to light yellow | [Specific Gravity]
1.14 | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT, IRRITANT-HARMFUL | [HS Code ]
29333990 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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