Ethyl 4-bromobutyrate Chemical Properties

Melting point:

98-100 °C

Boiling point:

80-82 °C/10 mmHg (lit.)

Density 

1.363 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.456(lit.)

Flash point:

195 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly)

form 

Liquid

Specific Gravity

1.363

color 

Clear colorless to yellow

Water Solubility 

immiscible

BRN 

1749700

InChIKey

XBPOBCXHALHJFP-UHFFFAOYSA-N

CAS DataBase Reference

2969-81-5(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 4-bromobutyrate(2969-81-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

2915900090

MSDS

• Language:English Provider:4-Bromobutyric acid ethyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl 4-bromobutyrate Usage And Synthesis

Description

Ethyl 4-bromobutyrate is a colourless volatile liquid organic or biological reagent. It is used in organic synthesis to prepare 4-bromobutyl ester, 4-bromobutyl amide and 4-bromobutyl ether. It is also used in the synthesis of poly(2,6-dimethyl-1,4-epoxyphenyl ether) and isotopic thieno[2,3-b]azepin-4-one thieno[2,3-b]-azepin-4-one with antitumour activity. In the biological field, it has been used in enzyme-linked immunosorbent assays for zilpaterol.

Chemical Properties

clear colorless to yellow liquid

Uses

A versatile building block and synthesis reagent

Uses

Ethyl 4-bromobutyrate is used as a building block for the preparation of firefly luciferase inhibitor-conjucated peptide derivatives. It finds application in the synthesis of poly(2,6,-dimethyl-1,4-phehylene oxide) and thieno(2,3-b)-azepin-4-ones.

Synthesis Reference(s)

The Journal of Organic Chemistry, 56, p. 2264, 1991 DOI: 10.1021/jo00006a061

Hazard

Strongly irritating to skin and eyes

Synthesis

Part A: Synthesis of ethyl 4-bromobutyrate To a solution of 4-bromobutyric acid (3 g, 18 mmol) in ethanol (30 mL) was added 5 mL of a dioxane solution of 4N HCl. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the volatile components were removed under vacuum. The concentrated residue was dissolved in 150 mL of dichloromethane. The organic phase was washed sequentially with saturated aqueous NaHCO3 (1 x 150 mL) and brine (1 x 150 mL), dried over anhydrous MgSO4, filtered, and the filtrate was concentrated under reduced pressure. The concentrated residue was dried under vacuum to give 3 g (85.5% yield) of ethyl 4-bromobutyrate as a yellow oil.1H NMR (300 MHz, CDCl3): δ1.22 (t, 3H, J = 7.15 Hz), 2.13 (m, 2H, J = 6.80 Hz), 2.45 (t, 2H, J = 7.15 Hz), 3.43 (t , 2H, J = 6.44Hz), 4.10 (q, 2H, J = 7.25Hz).

References

[1] Patent: US5753660, 1998, A

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