1-Chloroisobutyl propionate

1-Chloroisobutyl propionate Property

Boiling point:

166.7°C

Density 

1.030

Flash point:

56°C

storage temp. 

2-8°C

solubility 

Chloroform

Appearance

Colorless to light yellow Liquid

Safety

HS Code 

2915907098

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Chloroisobutyl propionate Chemical Properties,Usage,Production

Uses

Intermediate in the preparation of Fosinopril (F727800) derivatives.

Synthesis

Isobutyraldehyde (3 g, 41.6 mmol) was slowly added dropwise to propionyl chloride (3.85 g, 41.6 mmol) cooled to 0-5 °C under nitrogen protection, keeping the temperature in the range 0-5 °C. The reaction mixture was stirred continuously at this temperature for 4 hours. Upon completion of the reaction, the mixture was vacuum distilled at 50 °C to remove the volatile components, resulting in 2.59 g of a colorless liquid product, i.e., isobutyl propionyl-1-chloride (yield: 38%). The structure of the product was confirmed by 1H-NMR and 13C-NMR: 1H-NMR (CDCl3, 500MHz) δ 1.06 (t, J = 7.0Hz, 6H), 7.60 (t, J = 7.5Hz, 3H), 2.13-2.17 (m, 1H), 2.39 (q, J = 7.5Hz, 2H), 6.31 (d, J = 4.5 Hz, 1H); 13C-NMR (CDCl3, 125MHz) δ 8.66, 17.25, 17.36, 27.49, 35.19, 88.61, 172.16.

References

[1] Patent: US2008/125483, 2008, A1. Location in patent: Page/Page column 9
[2] Patent: WO2009/118580, 2009, A2. Location in patent: Page/Page column 23-24
[3] Patent: US2014/56849, 2014, A1. Location in patent: Paragraph 0306-0308
[4] Patent: CN103626765, 2016, B. Location in patent: Paragraph 0402; 0404; 0405
[5] Journal of the American Chemical Society, 1921, vol. 43, p. 665