4-Bromophenylacetic acid
{{Chembox
|Name = 4-Bromophenylacetic acid
|ImageFile = P-Bromophenylacetic acid.png
|ImageSize = 200
|ImageName = Structural formula
|ImageFile1 = 4-bromophenylacetic acid 3d.png
|ImageSize1 = 200
|ImageName1 = Van der Waals space-filling model of 4-bromophenylacetic acid
|ImageFile2 = 4-bromophenylacetic acid sample.jpg
|ImageSize2 = 100
|ImageName2 = 4-bromophenylacetic acid sample
|SystematicName = 2-(4-bromophenyl)acetic acid
|OtherNames = p-Bromophenylacetic acid
2-(4-bromobenzene)acetic acid
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 67229
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = WA6UT8W6AJ
|InChI = 1S/C8H7BrO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)
|InChIKey = QOWSWEBLNVACCL-UHFFFAOYSA-N
|PubChem = 74654
|EINECS = 217-523-7
| KEGG = C03076
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C8H7BrO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5H2,(H,10,11)
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = QOWSWEBLNVACCL-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 1878-68-8
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 1790
|SMILES = C1=CC(=CC=C1CC(=O)O)Br
}}
|Section2={{Chembox Properties
|C=8 | H=7 | Br=1 | O=2
|Appearance = White solid
|Odor = Honey-like
|MeltingPtC = 118
}}
|Section3={{Chembox Hazards
|ExternalSDS = [https://assets.thermofisher.com/DirectWebViewer/private/document.aspx?prd=ALFAAA15325~~PDF~~MTR~~CLP1~~EN~~2021-01-31%2004:50:30~~4-Bromophenylacetic%20acid~~ External MSDS]
|GHSPictograms = {{GHS07}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|318|319}}
|PPhrases = {{P-phrases|264|280|305+351+338|310|337+313}}
}}
}}
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.{{cite journal |last=Bedson |first=P. Philips |date=1880 |title=VIII.—On some derivatives of phenylacetic acid |journal=Journal of the Chemical Society, Transactions |volume=37 |pages=90–101 |doi=10.1039/CT8803700090|url=https://zenodo.org/record/1769194 }}
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.{{cite journal |last1=Khan |first1=Imtiaz |last2=Ibrar |first2=Aliya |last3=Ejaz |first3=Syeda Abida |last4=Khan |first4=Shafi Ullah |last5=Shah |first5=Syed Jawad Ali |last6=Hameed |first6=Shahid |last7=Simpson |first7=Jim |last8=Lecka |first8=Joanna |last9=Sévigny |first9=Jean |last10=Iqbal |first10=Jamshed |title=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 |journal=RSC Advances |date=2015 |volume=5 |issue=110 |pages=90806–90818 |doi=10.1039/C5RA14836G|bibcode=2015RSCAd...590806K }} 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.{{cite journal |last1=Field |first1=Jennifer A. |last2=Reed |first2=Ralph L. |title=Nonylphenol Polyethoxy Carboxylate Metabolites of Nonionic Surfactants in U.S. Paper Mill Effluents, Municipal Sewage Treatment Plant Effluents, and River Waters |journal=Environmental Science & Technology |date=1 November 1996 |volume=30 |issue=12 |pages=3544–3550 |doi=10.1021/es960191z|bibcode=1996EnST...30.3544F }}
Plant protoplasts conjugate aspartic acid with 4-bromophenylacetic acid to form 4-bromophenylacetyl-L-aspartic acid.{{cite journal |last1=Aranda |first1=Gérard |last2=Muller |first2=Jean-François |last3=Caboche |first3=Michel |title=Conjugation of aspartic acid with 4-bromophenylacetic acid, an auxin analogue of aspartic acid |journal=Phytochemistry |date=January 1987 |volume=26 |issue=8 |pages=2145–2147 |doi=10.1016/S0031-9422(00)84675-0}}
4-Bromophenylacetic acid reacts with sodium tetraphenylborate to form felbinac which can be further converted to xenbucin.{{cite journal |last1=Kuuloja |first1=Noora |last2=Kylmälä |first2=Tuula |last3=Xu |first3=Youjun |last4=Franzén |first4=Robert |title=Synthesis of Xenbucin using Suzuki reaction catalyzed by Pd/C in water |journal=Open Chemistry |date=1 September 2008 |volume=6 |issue=3 |pages=390–392 |doi=10.2478/s11532-008-0044-1|s2cid=94911885 |doi-access=free }}
Properties
References
{{reflist}}
{{DEFAULTSORT:Bromophenylacetic acid, 4-}}