Methyl 2,5-Dibromopentanoate Chemical Properties

Boiling point:

93-95°C 1mm

Density 

1,746 g/cm³

storage temp. 

2-8°C

solubility 

Chloroform (Slightly, Sonicated), Methanol (Slightly)

form 

Oil

color 

Colourless

InChI

InChI=1S/C6H10Br2O2/c1-10-6(9)5(8)3-2-4-7/h5H,2-4H2,1H3

InChIKey

YVHCGWPKBSEBTH-UHFFFAOYSA-N

SMILES

C(OC)(=O)C(Br)CCCBr

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2915705090

Methyl 2,5-Dibromopentanoate Usage And Synthesis

Uses

Methyl 2,5-Dibromopentanoate can be used for liquid crystal compounds for display devices.

Synthesis

The general procedure for the synthesis of methyl 2,5-dibromovalerate from tetrahydro-2H-pyran-2-one and methanol was as follows: 518 g of 6-valerol and 5 ml of phosphorus tribromide were added to an 11-necked, three-necked flask. The mixture was heated to 95 °C to 105 °C under stirring conditions, followed by the slow addition of 550 g of bromine while controlling the reaction temperature between 100 °C and 120 °C. After the reaction system was stabilized, another 5 ml of phosphorus tribromide and 236 g of bromine were added at 110 °C. After the addition was completed, the reaction mixture was allowed to stand for 30 minutes and subsequently cooled to between 0°C and 10°C. Next, 11 ml of methanol and 1 g of p-toluenesulfonic acid were added to the reaction system and the reaction temperature was maintained at 25 °C. After refluxing the reaction mixture for 5 hours, the excess reagent was removed by distillation and the lower organic phase was isolated. The organic phase was washed sequentially with 500 ml of 10% sodium hydroxide solution and 500 ml of water. After the washing was completed, the organic layer was separated and purified by fractional distillation (139 °C to 142 °C/28 hPa) to give 612.7 g of methyl 2,5-dibromopentanoate in 45% yield and >96% GC purity.

References

[1] Chemical Communications, 2015, vol. 51, # 70, p. 13470 - 13473
[2] Patent: WO2005/28449, 2005, A1. Location in patent: Page/Page column 11
[3] Tetrahedron, 1998, vol. 54, # 19, p. 4991 - 5004

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