Methyl 2,5-dibromobenzoate Chemical Properties

Melting point:

48-51 °C (lit.)

Boiling point:

291.3±20.0 °C(Predicted)

Density 

1.840±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Orange to Green

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

57381-43-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

N

HS Code 

2916399090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl 2,5-dibromobenzoate Usage And Synthesis

General Description

Methyl 2,5-dibromobenzoate, an aromatic ester, can be prepared from 2,5-dibromobenzoic acid via esterification with methanol. It undergoes Ni(0)-catalyzed polymerization to form soluble polyphenylenes.

Synthesis

Step 1: A methanol (2L) solution of 2,5-dibromobenzoic acid (250 g, 0.90 mol) and concentrated sulfuric acid (18.4 g, 0.19 mol) were added to a 2L round bottom flask. The reaction mixture was heated to reflux overnight and subsequently cooled to room temperature. The resulting precipitate was collected by filtration, washed with cold methanol and dried under vacuum to give 203.6 g of methyl 2,5-dibromobenzoate as a yellow solid. Step 2: To another 2L round-bottomed flask was added a solution of methyl 2,5-dibromobenzoate (198.2 g, 0.68 mol) in anhydrous DMF (1L). Copper cyanide (122 g, 1.36 mol) and sodium iodide (22.8 g, 0.15 mol) were subsequently added. The mixture was stirred at 130 °C overnight under nitrogen protection. Upon completion of the reaction, extraction was carried out with ethyl acetate (500 mL x 3), the organic layer was washed with water (500 mL), and finally purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford 95.2 g of methyl 2,5-dicyanobenzoate as a brown solid in 75.1% yield.

References

[1] Tetrahedron, 2016, vol. 72, # 24, p. 3454 - 3467
[2] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6655 - 6657

Methyl 2,5-dibromobenzoate(57381-43-8)Related Product Information

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