4-Bromophenylacetic acid

4-Bromophenylacetic acid, also known as p-bromophenylacetic acid, is an organic compound. It is a derivative of phenylacetic acid containing a bromine atom in the para position.

4-Bromophenylacetic acid
Structural formula
Van der Waals space-filling model of 4-bromophenylacetic acid
4-bromophenylacetic acid sample
Names
Systematic IUPAC name
2-(4-bromophenyl)acetic acid
Other names
p-Bromophenylacetic acid
2-(4-bromobenzene)acetic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.931
EC Number
  • 217-523-7
KEGG
UNII
  • InChI=1S/C8H7BrO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11) checkY
    Key: QOWSWEBLNVACCL-UHFFFAOYSA-N checkY
  • InChI=1S/C8H7BrO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)
    Key: QOWSWEBLNVACCL-UHFFFAOYSA-N
  • C1=CC(=CC=C1CC(=O)O)Br
Properties
C8H7BrO2
Molar mass 215.046 g·mol−1
Appearance White solid
Odor Honey-like
Melting point 118 °C (244 °F; 391 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Danger
H318, H319
P264, P280, P305+P351+P338, P310, P337+P313
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 Phenylacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

4-Bromophenylacetic acid may be prepared by the addition of a bromine atom to phenylacetic acid through electrophilic aromatic substitution. It was first prepared in the laboratory by treatment of phenylacetic acid with bromine and mercuric oxide; a mixture of the 2- and 4- isomers is made, and the 4- isomer is isolated by fractional crystallization.[1]

It can also be made by condensing 4-bromobenzylbromide with sodium cyanide in ethanol, and the hydrolising the nitrile with sodium hydroxide.[2]

Reactions

Methyl 2-(4-bromophenyl)acetate is made from 4-bromophenylacetic acid by refluxing it with methanol acidified with sulfuric acid.[3]

An ethyl ester can be made in an analogous way.[4]

A hydrazone derivative, 2-(4-bromophenyl)acetohydrazide, is made by refluxing the methyl ester with hydrazine.[3] Further hydrazone derivatives of 4-bromophenylacetic acid are made by condensing the simple hydrazone with aldehydes, forming a double bond with the second nitrogen.[3] At least 19 of these hydrazones are known.[3]

4-Bromophenylacetic acid is a chemical that can be purchased.[5]

Plant protoplasts conjugate aspartic acid with 4-bromophenylacetic acid to form 4-bromophenylacetyl-L-aspartic acid.[2]

4-Bromophenylacetic acid reacts with sodium tetraphenylborate to form felbinac which can be further converted to xenbucin.[4]

Properties

The ionic conductance has been measured.[6]

See also

References
  1. Bedson, P. Philips (1880). "VIII.—On some derivatives of phenylacetic acid". Journal of the Chemical Society, Transactions. 37: 90–101. doi:10.1039/CT8803700090.
  2. Aranda, Gérard; Muller, Jean-François; Caboche, Michel (January 1987). "Conjugation of aspartic acid with 4-bromophenylacetic acid, an auxin analogue of aspartic acid". Phytochemistry. 26 (8): 2145–2147. doi:10.1016/S0031-9422(00)84675-0.
  3. Khan, Imtiaz; Ibrar, Aliya; Ejaz, Syeda Abida; Khan, Shafi Ullah; Shah, Syed Jawad Ali; Hameed, Shahid; Simpson, Jim; Lecka, Joanna; Sévigny, Jean; Iqbal, Jamshed (2015). "Influence of the diversified structural variations at the imine functionality of 4-bromophenylacetic acid derived hydrazones on alkaline phosphatase inhibition: synthesis and molecular modelling studies". RSC Advances. 5 (110): 90806–90818. Bibcode:2015RSCAd...590806K. doi:10.1039/C5RA14836G.
  4. Kuuloja, Noora; Kylmälä, Tuula; Xu, Youjun; Franzén, Robert (1 September 2008). "Synthesis of Xenbucin using Suzuki reaction catalyzed by Pd/C in water". Open Chemistry. 6 (3): 390–392. doi:10.2478/s11532-008-0044-1. S2CID 94911885.
  5. Field, Jennifer A.; Reed, Ralph L. (1 November 1996). "Nonylphenol Polyethoxy Carboxylate Metabolites of Nonionic Surfactants in U.S. Paper Mill Effluents, Municipal Sewage Treatment Plant Effluents, and River Waters". Environmental Science & Technology. 30 (12): 3544–3550. Bibcode:1996EnST...30.3544F. doi:10.1021/es960191z.
  6. Holze, Rudolf (2016). "Ionic conductance of p-bromophenylacetic acid". Electrochemistry: 573. doi:10.1007/978-3-662-49251-2_540. ISBN 978-3-662-49249-9.
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