2-Bromo-4-butanolide Chemical Properties

Boiling point:

138 °C/6 mmHg (lit.)

Density 

1.786 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.508(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Acetone, Chloroform, Ethyl Acetate, Methanol

form 

Clear Colourless to Light Yellow Liquid

Specific Gravity

1.778 (20/4℃)

Appearance

Colorless to light yellow Liquid

Sensitive 

Moisture Sensitive/Lachrymatory

BRN 

107800

InChI

InChI=1S/C4H5BrO2/c5-3-1-2-7-4(3)6/h3H,1-2H2

InChIKey

LFJJGHGXHXXDFT-UHFFFAOYSA-N

SMILES

O1CCC(Br)C1=O

CAS DataBase Reference

5061-21-2(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Furanone, 3-bromodihydro-(5061-21-2)

EPA Substance Registry System

2(3H)-Furanone, 3-bromodihydro- (5061-21-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 2810

WGK Germany 

3

F 

21

Hazard Note 

Irritant/Keep Cold/Lachrymatory/Moisture Sensitive

TSCA 

Yes

HS Code 

29322980

MSDS

• Language:English Provider:2-Bromo-4-hydroxybutyric acid gamma-lactone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Bromo-4-butanolide Usage And Synthesis

Chemical Properties

Pale Yellow Liquid

Uses

Lactams inhibit type Q arylesterase activity of human serum paraoxonase PON1.

Synthesis

General procedure for the synthesis of α-bromo-γ-butyrolactone from γ-butyrolactone (bromination step): in a 1000 mL reaction vessel equipped with a stirring device, refluxing device, thermometer, dropping funnel, and nitrogen introduction tube, 200 g (2.32 mol) of γ-butyrolactone and 2.76 g (0.086 mol based on 3.7 mol% of γ-butyrolactone) of sulfur were added as the catalyst. 431 g (2.70 mol) of bromine was loaded into a dropping funnel. Stirring was initiated, the reaction temperature was controlled not to exceed 40 °C, and the bromine was slowly added dropwise. After the dropwise addition was completed, the reaction temperature was raised to about 90 °C and the reaction was maintained at this temperature for 1 hour. Subsequently, the temperature was raised to about 110°C and the reaction was continued for 3 hours.

References

[1] Patent: JP5837752, 2015, B2. Location in patent: Paragraph 0052; 0079-0081; 0082; 0085; 0086; 0088
[2] Journal of Porphyrins and Phthalocyanines, 2010, vol. 14, # 1, p. 89 - 100
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 3074 - 3077
[4] Synlett, 2005, # 17, p. 2648 - 2652
[5] Organic Letters, 2011, vol. 13, # 14, p. 3670 - 3673

2-Bromo-4-butanolide(5061-21-2)Related Product Information

• BETA-BUTYROLACTONE
• TRIOXSALEN
• Citric acid
• Tungsten
• p-Toluenesulfonic acid
• Dimethyl sulfoxide
• Sodium carbonate
• Zinc oxide
• Manganese dioxide
• Diethylstilbestrol
• Bromine
• Gamma Butyrolactone
• ALPHA-BROMO-ALPHA-METHYL-GAMMA-BUTYROLACTONE
• ALPHA-BROMO-GAMMA-VALEROLACTONE
• 2-Bromo-4-butanolide
• SALOR-INT L132004-1EA
• A-BROMO-A-TRIFLUOROACETYL-G-BUTYROLACTONE, HYDRATE