3-Bromopropylacetate Chemical Properties

Boiling point:

163°C(lit.)

Density 

1.417±0.06 g/cm3(Predicted)

refractive index 

1.4560 to 1.4600

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Safety Information

HS Code 

2915.39.9000

3-Bromopropylacetate Usage And Synthesis

Synthesis

General procedure for the synthesis of propyl 3-bromoacetate from ethanoic anhydride and 3-bromo-1-propanol: To a stirred solution of 3-bromo-1-propanol (8.0 g, 57.55 mmol) in anhydrous dichloromethane (40 mL) was added triethylamine (12 mL, 86.32 mmol) and stirred for 1 h at room temperature. Ethanoic anhydride (6.5 mL, 69.06 mmol) dissolved in dichloromethane (5 mL) was added dropwise at 0 °C, followed by stirring for 16 h at room temperature. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was quenched with 1N hydrochloric acid solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography with 10% ethyl acetate/hexane as eluent to give the target product propyl 3-bromoacetate. Yield: 10.0 g, 96% yield; 1H NMR (400 MHz, CDCl3) δ 4.19-4.17 (m, 2H), 3.47 (t, J=6.5 Hz, 2H), 2.21-2.18 (m, 2H), 2.06 (s, 3H).

References

[1] Patent: WO2017/6283, 2017, A1. Location in patent: Paragraph 0474; 0475
[2] Patent: WO2018/98206, 2018, A1. Location in patent: Paragraph 0940
[3] Patent: WO2008/39999, 2008, A1. Location in patent: Page/Page column 49
[4] Patent: TW2017/8220, 2017, A. Location in patent: Page/Page column 73; 74
[5] Chemistry - A European Journal, 2003, vol. 9, # 14, p. 3353 - 3366

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