1-Bromo-5-hexanone Chemical Properties

Boiling point:

216°C (rough estimate)

Density 

1.3494

refractive index 

1.4890 (estimate)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

soluble in Chloroform

form 

Oil

color 

Colourless

CAS DataBase Reference

10226-29-6(CAS DataBase Reference)

1-Bromo-5-hexanone Usage And Synthesis

Chemical Properties

Colourless Oil

Uses

6-Bromo-2-hexanone (cas# 10226-29-6) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 6-bromo-2-hexanone using 1-methylcyclopentanol as starting material was as follows: a mixture of 1-methylcyclopentanol (4.00 g, 39.94 mmol) and potassium carbonate (K2CO3, 33.11 g, 239.6 mmol) in chloroform (CHCl3, 130 mL) was stirred for 15 min at 0 °C. Subsequently, bromine (10.23 mL, 199.7 mmol) was added slowly. The reaction mixture was continued to be stirred at 0°C for 2.5 hours. Upon completion of the reaction, the mixture was slowly poured into ice-cold saturated aqueous sodium thiosulfate (Na2S2O3, 100 mL). The organic layer was separated, washed with water (2 x 100 mL), dried over magnesium sulfate (MgSO4), filtered and concentrated in vacuum. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, 3:1) to afford the target product 6-bromo-2-hexanone as a colorless oil (4 g) in 56% yield (98% purity, UV detection at 214 nm, no ESI signal detected). The 1H-NMR (400 MHz, CDCl3) data of the product were as follows: δ1.66-1.80 (m, 2H), 1.82-1.93 (m, 2H), 2.15 (s, 3H), 2.48 (t, J=7.3 Hz, 2H), 3.41 (t, J=6.5 Hz, 2H).

References

[1] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5831 - 5833
[2] Patent: US2018/244648, 2018, A1. Location in patent: Page/Page column 0289; 0290
[3] Russian Chemical Bulletin, 1999, vol. 48, # 11, p. 2080 - 2082
[4] Patent: WO2009/77990, 2009, A1. Location in patent: Page/Page column 63-64
[5] Patent: US2011/34516, 2011, A1. Location in patent: Page/Page column 34

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