p-Bromophenoxyacetic acid Chemical Properties

Melting point:

149-153 °C(lit.)

Boiling point:

337.9±17.0 °C(Predicted)

Density 

1.6494 (rough estimate)

refractive index 

1.4730 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.09±0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

1878-91-7(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, (4-bromophenoxy)- (1878-91-7)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29189900

MSDS

• Language:English Provider:(4-Bromophenoxy)acetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

p-Bromophenoxyacetic acid Usage And Synthesis

Chemical Properties

White or cream crystalline powder

Uses

4-Bromophenoxyacetic acid may be used as a starting material in the preparation of radioiodinated phenoxyacetic acid derivatives with potential application as radiopharmaceuticals.

General Description

4-Bromophenoxyacetic acid, also known as p-bromophenoxyacetate, is a phenoxyalkanoic acid derivative. It is a chemical elicitor that can induce β-glucuronidase (GUS) activity in rice.

Synthesis

The general procedure for the synthesis of 4-bromophenoxyacetic acid from 4-bromophenol and chloroacetic acid was as follows: a mixture of NaOH (0.04 mol, 1.60 g), deionized water (20 mL), and ethanol (20 mL) was added to a 150 mL three-necked flask, followed by the slow addition of 4-bromophenol (0.04 mol, 6.92 g). After 20 minutes of reaction under stirring, aqueous sodium chloroacetate solution was added dropwise. The reaction mixture was heated to 105 °C and refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the pH of the mixture was adjusted to 1-2 with dilute hydrochloric acid. the precipitate was collected by filtration and washed several times with dilute hydrochloric acid. Finally, the product was purified by recrystallization and dried under vacuum to give 4-bromophenoxyacetic acid as a white solid.

Purification Methods

Crystallise the acid from EtOH or H2O (m 161.4-161.8o). [Hayes & Branch J Am Chem Soc 65 1555 1943, Beilstein 6 III 747, 6 IV 1052.]

References

[1] Luminescence, 2018, vol. 33, # 5, p. 855 - 862
[2] Synthetic Communications, 2004, vol. 34, # 3, p. 377 - 382
[3] Journal of Molecular Structure, 2014, vol. 1074, p. 487 - 495
[4] Journal of Fluorescence, 2015, vol. 25, # 4, p. 849 - 859
[5] Luminescence, 2015, vol. 30, # 5, p. 677 - 685

p-Bromophenoxyacetic acid(1878-91-7)Related Product Information

• 1-Bromo-4-tert-butylbenzene
• Fluroxypyr
• Stearic acid
• Folic acid
• Phenoxyacetic acid
• 4'-Bromopropiophenone
• 4-Chlorophenoxyacetic acid
• Allyl phenoxyacetate
• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Bromophenylacetic acid
• 2-Bromophenylacetic acid
• 4-Bromofluorobenzene
• Citric acid
• Ascoric Acid
• 2,4-DIBROMOPHENOXYACETIC ACID
• Acetic anhydride
• Phenylacetic acid
• O-BROMOPHENOXYACETIC ACID