4-Bromophenylacetic acid

4-Bromophenylacetic acid
Names
	Systematic IUPAC name 2-(4-bromophenyl)acetic acid
	Other names p-Bromophenylacetic acid; 2-(4-bromobenzene)acetic acid
Identifiers
CAS Number	1878-68-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:1790 ;
ChemSpider	67229 ;
ECHA InfoCard	100.015.931
EC Number	217-523-7;
KEGG	C03076;
PubChem CID	74654;
UNII	WA6UT8W6AJ ;
CompTox Dashboard (EPA)	DTXSID2062032 ;
	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−1
Appearance	White solid
Odor	Honey-like
Melting point	118 °C (244 °F; 391 K)
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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.^[1]

It can also be made by condensing 4-bromobenzyl bromide with sodium cyanide in ethanol, and then hydrolyzing the nitrile with sodium hydroxide.^[2]

Reactions

Methyl 4-bromophenylacetate is made from 4-bromophenylacetic acid by Fischer esterification, refluxing it with methanol acidified with sulfuric acid.^[3] An ethyl ester can be made in an analogous way using ethanol instead of methanol.^[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]

References

^ Bedson, P. Philips (1880). "VIII.—On some derivatives of phenylacetic acid". Journal of the Chemical Society, Transactions. 37: 90–101. doi:10.1039/CT8803700090.
^ ^a ^b 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.
^ ^a ^b ^c ^d 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.
^ ^a ^b 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.
^ 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.
^ 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.

[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.

[aranda-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.

[khan-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.

[kuuloja-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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