Synthesis of 4-(trichloromethyl)pyridine

Preparation of 4-(trichloromethyl)pyridine

Preparation of 4-(trichloromethyl)pyridine

Preparation of 4-(trichloromethyl)pyridine

Dry gaseous chlorine (50 g, 3 moles per mole of 4-methylpyridine) is passed into a mixture of 4-methylpyridine (21 ml), acetic anhydride (20 ml), sodium acetate (60 g), and acetic acid (250 ml) kept at 80° C. The mixture is then poured on ice, made alkaline with ammonia, and extracted several times with ether. Two vacuum-fractionations of the oil obtained from the extract yields 15.4 g of  4-(trichloromethyl)pyridine, b.p. 105-107°/18 mm. The 4-(trichloromethyl)pyridine is not stable and decomposes in a few days.

J. Chem. Soc, 1951, 1145

J. Chem. Soc, 1939, 781.

IUPAC Name

4-(trichloromethyl)pyridine

InChI

InChI=1S/C6H4Cl3N/c7-6(8,9)5-1-3-10-4-2-5/h1-4H

InChI Key

JYQFHKYYTOIWOQ-UHFFFAOYSA-N

Canonical SMILES

C1=CN=CC=C1C(Cl)(Cl)Cl

Depositor-Supplied Synonyms

4-(Trichloromethyl)pyridine, 22796-40-3, AC1L3IPL, AC1Q3GSW, Pyridine,4-(trichloromethyl)-, SCHEMBL5720583, CTK4F0203, EINECS 245-226-2, AR-1F7300, ZINC31331437, AKOS006331871, HE042393, KB-35289, FT-0692350, A816359

Removed Synonyms

4- PYRIDINE, CID89838, 2340-57-0

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