Uses
It is used as pharmaceutical intermediate. Many organisms use 1,9-dichlorononane as a sole carbon source. Bacteria on incubation of sewage with 1,9-dichlorononane increased its subsequent capacity to dehalogenate.
Synthesis
General procedure for the synthesis of 1,9-dichlorononane from 1,9-nonanediol: 1,9-nonanediol (5.0 g, 31.2 mmol), dichloromethane (100 mL), and DMF (3 drops) were added to a 500 mL eggplant-shaped vial. Thionyl chloride (11.7 g, 98.3 mmol) was dissolved in dichloromethane (155 mL). The thionyl chloride solution was slowly added dropwise to a cigar shaped flask under ice bath conditions. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the reaction mixture was washed with saturated sodium bicarbonate solution followed by saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1,9-dichlorononane (4.0 g, light yellow oil, 65% yield).
References
[1] Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 4.1, p. 642 - 646
[2] Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 4, p. 716 - 721
[3] Patent: CN107721925, 2018, A. Location in patent: Paragraph 0096; 0097
[4] Journal of the American Chemical Society, 1948, vol. 70, p. 3393
[5] Pharmaceutical Chemistry Journal, 1972, vol. 6, # 5, p. 283 - 286
