ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Ethyl ester compound Ethyl 4-bromobutyrate

Ethyl 4-bromobutyrate

Product NameEthyl 4-bromobutyrate
CAS2969-81-5
MFC6H11BrO2
MW195.05
EINECS221-005-6
MOL File2969-81-5.mol

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
InChI	1S/C6H11BrO2/c1-2-9-6(8)4-3-5-7/h2-5H2,1H3
InChIKey	XBPOBCXHALHJFP-UHFFFAOYSA-N
SMILES	CCOC(=O)CCCBr
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
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

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

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

2623-87-2

2969-81-5

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

Preparation Products And Raw materials