ChemicalBook CAS DataBase List 4-bromobutyl nitrate

4-bromobutyl nitrate synthesis

1synthesis methods

Product Name:4-bromobutyl nitrate
CAS Number:146563-40-8
Molecular formula:C4H8BrNO3
Molecular Weight:198.02

4-Bromobutyl nitrate is a thermally unstable oily liquid, which is used to obtain nitrooxyalkyl esters of pharmacologically active carboxylic acids (WO 04/020384, WO 04/020385). 4-Bromobutyl nitrate not dissolved in solvents is added to the solution / suspension of pharmacologically active carboxylic acids such as naproxen, ferulic acid, etc. 4-Bromobutyl nitrate is obtained by nitration with a sulfonitizing mixture of 4-bromo-1-hydroxybutane (Chem. Pharm. Bull., 1993, 41, p. 1040). The reaction is carried out by adding 4-bromo-1-hydroxybutane to the crude sulphonating mixture in the absence of solvents or diluents. The reaction is limited to a laboratory scale since the method is potentially explosive due to a sudden increase in temperature and gas production.
https://patents.google.com/patent/RU2388746C2/en

33036-62-3 Synthesis

33036-62-3
226 suppliers
$45.00/1g

146563-40-8
11 suppliers
inquiry

Yield:146563-40-8 96%

Reaction Conditions:

with sulfuric acid;nitric acid in dichloromethane at -5 - 5; for 2 - 5 h;

Steps:

1.II.2

11. 2; Preparation of nitrate; In reactor cooled to-5 to 5°C, nitric acid fuming (8.5 g- 135 mmol) was slowly added to a solution of 98% sulfuric acid (13.0 g-130 mmol) in dichloromethane (18.0 g-212 mmol). 4-bromobutanol (10.2 g-66. 6 mmol) was then added to this mixture and the reaction medium was stirred at-5 to 5°C over a period of 2-5 hours. The mixture was poured into cold water (110 g) keeping the temperature between-5 °C and 3°C. After decantation, the upper aqueous phase was extracted with dichloromethane and the combined organic phases were washed with water, adjusted to pH=6-7 by addition of 27. 65% sodium hydroxide, washed with brine and dried over magnesium sulfate. Dichloromethane was distilled off under vacuum and crude 4-bromobutyl nitrate (12.7 g- 64.1 mmol) was recovered in a yield of about 96%.

References:

WO2005/68421,2005,A1 Location in patent:Page/Page column 36