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Saving copy of the {{chembox}} taken from revid 443315357 of page 2-Iodobenzoic_acid for the Chem/Drugbox validation project (updated: '').
 
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:2-Iodobenzoic_acid|oldid=443315357}} 443315357] of page [[2-Iodobenzoic_acid]] with values updated to verified values.}}
{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 443314464
| verifiedrevid = 477213655
| Name = 2-Iodobenzoic acid
| Name = 4-Iodobenzoic acid
| Reference =
| Reference =
⚫
| ImageFile = 2-Iodobenzoic acid.svg
| ImageFile = 4-iodobenzoic acid structure.png
| ImageSize = 120px
| ImageSize = 150px
⚫
| IUPACName = 2-Iodobenzoic acid
| OtherNames = ''o''-Iodobenzoic acid
| ImageFile1 = 4-iodobenzoic acid 3d.png
| ImageSize1 = 150px
⚫
| Section1 = {{Chembox Identifiers
| ImageFile2 = 4-iodobenzoic acid.jpg
⚫
| CASNo = 88-67-5
| ImageSize2 = 100px
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
⚫
| PIN = 4-Iodobenzoic acid
⚫
| PubChem = 6941
⚫
| OtherNames = ''p''-Iodobenzoic acid
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
|Section1={{Chembox Identifiers
⚫
| ChemSpiderID = 6675
⚫
| CASNo = 619-58-9
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEBI = 287979
| EINECS = 210-603-2
| SMILES = O=C(O)c1ccccc1I
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 112424
| ChEMBL = 101265
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChemSpiderID = 11588
⚫
| PubChem = 12085
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IPO4LYQ1EN
| SMILES = C1=CC(=CC=C1C(=O)O)I
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C7H5IO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
| StdInChI=InChI=1S/C7H5IO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey=CJNZAXGUTKBIHP-UHFFFAOYSA-N
| StdInChIKey=GHICCUXQJBDNRN-UHFFFAOYSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
|C=7|H=5|I=1|O=2
| Formula = C<sub>7</sub>H<sub>5</sub>IO<sub>2</sub>
⚫
| Appearance = white solid
| MolarMass = 248.018
| Density = 2.18 g/cm<sup>3</sup>
⚫
| Appearance =
| Density =
| MeltingPtC = 270-273
| MeltingPt_ref = <ref>{{cite web |url=https://www.sigmaaldrich.com/US/en/product/aldrich/206547 |title=4-Iodobenzoic acid |author=<!--Not stated--> |website=[[Sigma Aldrich]] |access-date=January 31, 2023}}</ref>
| MeltingPtC = 162
| BoilingPt =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
| GHS_ref=<ref>{{cite web |title=4-Iodobenzoic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/12085#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| MainHazards =
| GHSPictograms = {{GHS07}}
| FlashPt =
| GHSSignalWord = Warning
| Autoignition =
| HPhrases = {{H-phrases|315|319|335}}
}}
| PPhrases = {{P-phrases|261|264|264+265|271|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|403+233|405|501}}
| Section7 = {{Chembox Hazards
| NFPA-H =
| NFPA-F =
| NFPA-R =
| ExternalMSDS =
}}
}}
}}
}}

'''4-Iodobenzoic acid''', or ''p''-iodobenzoic acid, is an isomer of [[iodobenzoic acid]].<ref>{{cite web |title=4-Iodobenzoic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/4-Iodobenzoic-acid |access-date=2023-01-21 |website=[[PubChem]] |language=en}}</ref>

==Structure==
[[File:4-iodobenzoic acid crystallization.png|thumb|left|4-iodobenzoic acid crystallization<ref name="solidstate"/>]]
[[X-ray crystallography]] of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded [[Dimer (chemistry)|dimers]] which [[Stacking (chemistry)|stack]] perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to [[van der Waals forces]].<ref name="solidstate">{{cite journal |last1=Nygren |first1=Cara L. |last2=Wilson |first2=Chick C. |last3=Turner |first3=John F. C. |date=2005 |title=On the Solid State Structure of 4-Iodobenzoic Acid |journal=[[The Journal of Physical Chemistry A]] |volume=109 |issue=11 |pages=2586–2593 |doi=10.1021/jp047189b|pmid=16833563 |bibcode=2005JPCA..109.2586N }}</ref>

==Preparation==
4-Iodobenzoic acid may be prepared in the laboratory by the oxidation of [[4-Iodotoluene|''p''-iodotoluene]] with [[potassium permanganate]].<ref>{{cite journal |last1=Varma |first1=P. S. |last2=Panickerp |first2=P. B. |date=1928 |title=Influence of substitution on the oxidation of side chains in the benzene nucleus |journal=Proc. 15th Indian Sci. Cong.}}</ref>

==Reactions==
The carboxylic acid functionality of 4-iodobenzoic acid undergoes [[Fischer–Speier esterification]] with [[methanol]] to form the ester [[methyl 4-iodobenzoate]].<ref>{{cite journal |last1=Gadzikwa |first1=Tendai |last2=Zeng |first2=Bi-Shun |last3=Hupp |first3=Joseph T. |last4=Nguyen |first4=SonBinh T. |date=2008 |title=Ligand-elaboration as a strategy for engendering structural diversity in porous metal–organic framework compounds |journal=[[Chemical Communications]] |issue=31 |pages=3672–3674 |doi=10.1039/B714160B|pmid=18665295 }}</ref>

==References==
{{reflist}}

{{DEFAULTSORT:Iodobenzoic acid, 4-}}
[[Category:Benzoic acids]]
[[Category:4-Iodophenyl compounds]]
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