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4-Bromophenylacetic acid

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.931 Edit this at Wikidata
EC Number
  • 217-523-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
  • 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
SMILES
  • C1=CC(=CC=C1CC(=O)O)Br
Properties
Chemical formula C8H7BrO2
Molar mass 215.046 g·mol
Appearance White solid
Odor Honey-like
Melting point 118 °C (244 °F; 391 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Danger
Hazard statements H318, H319
Precautionary statements P264, P280, P305+P351+P338, P310, P337+P313
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

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.

It can also be made by condensing 4-bromobenzyl bromide with sodium cyanide in ethanol, and then hydrolyzing the nitrile with sodium hydroxide.

Reactions

Methyl 4-bromophenylacetate is made from 4-bromophenylacetic acid by Fischer esterification, refluxing it with methanol acidified with sulfuric acid. An ethyl ester can be made in an analogous way using ethanol instead of methanol.

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

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

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

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

Properties

The ionic conductance has been measured.

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. p. 573. doi:10.1007/978-3-662-49251-2_540. ISBN 978-3-662-49249-9.
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