Preparation method of 2,6-bis(di-tert-butylmethylphosphate)pyridine_Industrial additives

Background and overview^[1-2]

2,6-bis(di-tert-butylmethylphosphate)pyridine is an organic intermediate that can be nucleophilically substituted by 2,6-bis(chloromethyl)-pyridine and di-tert-butylphosphine. get. 2,6-Bis(di-tert-butylmethylphosphate)pyridine can be used to produce high-quality and reproducible inorganic films on solid substrates. The film may act as a dielectric, as a fine-structured separator or as an electrical contact in a transistor, preferably as an electrical contact.

Preparation^[1]

Di-tert-butylphosphine (1.25 g, 8.6 mmol) was added dropwise to a suspension of 2,6-bis(chloromethyl)-pyridine (710 mg, 4.0 mmol) in methanol (3 mL) . The mixture was heated to 45°C and stirred for 2 days. After cooling to room temperature, triethylamine (1.25 mL) was slowly added and a white precipitate formed. The solvent was evaporated in vacuo and the compound 2,6-bis(di-tert-butylphosphomethyl)pyridine was isolated from the residue by column chromatography (silica, solvent: chloroform) as a white solid. Yield: 1.25g (79%). 31P {1H} NMR (CDCl3): 37.49 (s). 1H NMR (CDCl3): 1.14 (d, 3JPH = 11.0 Hz, 36H, PC(CH3)3), 3.01 (d, 2JPH = 3.3 Hz, 4H, CH2 Antiaging agent rdP), 7.25 (d, 3JHH = 7.7 Hz, 2H, pyridine-H3,5), 7.47 (dd, 3JHH =7.8 Hz, 1H, pyridine-H4). 13C{1H} NMR (CDCl3): 29.69 ( d, 2JPC = 13.2 Hz, PC(CH3)3), 31.67 (d, 1JPC = 23.4 Hz, CH2P), 31.83 (d, 1JPC = 21.4 Hz, CH2P), 120.69 (dd, 3JPC = 10.8 Hz, 5JPC = 1.35 Hz, pyridine-C3,5), 136.08 (s, pyridine-C4), 161.89 (d, 2JPC = 14.6 Hz, pyridine-C2,5) (assignment of 13C{1H} NMR signals was confirmed by 13C DEPT). MS (EI), m/z (%): 396 (5) [M+], 338 (100) [M+ – C(CH3)3]. Anal. Calcd: C, 69.75; H, 10.87. Found: C, 69.36 ; H, 11.08.