| Revision as of 17:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 443315357 of page 2-Iodobenzoic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:55, 7 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Iodobenzene derivatives; added Category:4-Iodophenyl compounds using HotCat |
| Line 1: |
Line 1: |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] 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=] |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 ].<ref>{{cite web |title=4-Iodobenzoic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/4-Iodobenzoic-acid |access-date=2023-01-21 |website=] |language=en}}</ref> |
|
|
|
|
|
==Structure== |
|
|
] |
|
|
] of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded ] which ] perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to ].<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=] |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 ] with ].<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 ] with ] to form the ester ].<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=] |issue=31 |pages=3672–3674 |doi=10.1039/B714160B|pmid=18665295 }}</ref> |
|
|
|
|
|
==References== |
|
|
{{reflist}} |
|
|
|
|
|
{{DEFAULTSORT:Iodobenzoic acid, 4-}} |
|
|
] |
|
|
] |