4-Iodobenzoic acid: Difference between revisions

4-Iodobenzoic acid
Names
	Preferred IUPAC name 4-Iodobenzoic acid
	Other names p-Iodobenzoic acid
Identifiers
CAS Number	619-58-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL101265;
ChemSpider	11588 ;
ECHA InfoCard	100.009.641
EC Number	210-603-2;
PubChem CID	12085;
UNII	IPO4LYQ1EN ;
CompTox Dashboard (EPA)	DTXSID20862304 ;
	InChI InChI=1S/C7H5IO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10) Key: GHICCUXQJBDNRN-UHFFFAOYSA-N ;
	SMILES C1=CC(=CC=C1C(=O)O)I;
Properties
Chemical formula	C7H5IO2
Molar mass	248.019 g·mol−1
Appearance	white solid
Density	2.18 g/cm3
Melting point	270–273 °C (518–523 °F; 543–546 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 15:55, 7 September 2024

4-Iodobenzoic acid, or p-iodobenzoic acid, is an isomer of iodobenzoic acid.^[3]

Structure

X-ray crystallography of 4-iodobenzoic acid has shown that it crystallizes in the solid state as hydrogen-bonded dimers which stack perpendicular to their aromatic rings. The iodine atoms of adjacent dimers are also oriented towards each other due to van der Waals forces.^[4]

Preparation

4-Iodobenzoic acid may be prepared in the laboratory by the oxidation of p-iodotoluene with potassium permanganate.^[5]

Reactions

The carboxylic acid functionality of 4-iodobenzoic acid undergoes Fischer–Speier esterification with methanol to form the ester methyl 4-iodobenzoate.^[6]

References

^ "4-Iodobenzoic acid". Sigma Aldrich. Retrieved January 31, 2023.
^ "4-Iodobenzoic acid". pubchem.ncbi.nlm.nih.gov.
^ "4-Iodobenzoic acid". PubChem. Retrieved 2023-01-21.
^ ^a ^b Nygren, Cara L.; Wilson, Chick C.; Turner, John F. C. (2005). "On the Solid State Structure of 4-Iodobenzoic Acid". The Journal of Physical Chemistry A. 109 (11): 2586–2593. Bibcode:2005JPCA..109.2586N. doi:10.1021/jp047189b. PMID 16833563.
^ Varma, P. S.; Panickerp, P. B. (1928). "Influence of substitution on the oxidation of side chains in the benzene nucleus". Proc. 15th Indian Sci. Cong.
^ Gadzikwa, Tendai; Zeng, Bi-Shun; Hupp, Joseph T.; Nguyen, SonBinh T. (2008). "Ligand-elaboration as a strategy for engendering structural diversity in porous metal–organic framework compounds". Chemical Communications (31): 3672–3674. doi:10.1039/B714160B. PMID 18665295.

[1] "4-Iodobenzoic acid". Sigma Aldrich. Retrieved January 31, 2023.

[2] "4-Iodobenzoic acid". pubchem.ncbi.nlm.nih.gov.

[3] "4-Iodobenzoic acid". PubChem. Retrieved 2023-01-21.

[solidstate-4] Nygren, Cara L.; Wilson, Chick C.; Turner, John F. C. (2005). "On the Solid State Structure of 4-Iodobenzoic Acid". The Journal of Physical Chemistry A. 109 (11): 2586–2593. Bibcode:2005JPCA..109.2586N. doi:10.1021/jp047189b. PMID 16833563.

[5] Varma, P. S.; Panickerp, P. B. (1928). "Influence of substitution on the oxidation of side chains in the benzene nucleus". Proc. 15th Indian Sci. Cong.

[6] Gadzikwa, Tendai; Zeng, Bi-Shun; Hupp, Joseph T.; Nguyen, SonBinh T. (2008). "Ligand-elaboration as a strategy for engendering structural diversity in porous metal–organic framework compounds". Chemical Communications (31): 3672–3674. doi:10.1039/B714160B. PMID 18665295.

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[2]

[3]

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[6]

@@ Line 5: / Line 5: @@
 | Reference =
 | ImageFile = 4-iodobenzoic acid structure.png
-| ImageSize = 120px
+| ImageSize = 150px
 | ImageFile1 = 4-iodobenzoic acid 3d.png
-| ImageSize1 = 120px
+| ImageSize1 = 150px
 | ImageFile2 = 4-iodobenzoic acid.jpg
 | ImageSize2 = 100px
@@ Line 30: / Line 30: @@
   }}
 |Section2={{Chembox Properties
+|C=7|H=5|I=1|O=2
-| Formula = C<sub>7</sub>H<sub>5</sub>IO<sub>2</sub>
-| MolarMass = 248.018 g/mol
 | Appearance = white solid
+| Density = 2.18 g/cm<sup>3</sup>
 | 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>
   }}
-| Section7 = {{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>
 | GHSPictograms = {{GHS07}}
@@ Line 43: / Line 43: @@
 | 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}}
   }}
-| Section8 = {{Chembox Related
-| OtherCompounds = [[2-Iodobenzoic acid]]
- }}
 }}
-'''4-Iodobenzoic acid''',  or ''p''-iodobenzoic acid, is an [[organic compound]] with the formula IC<sub>6</sub>H<sub>4</sub>COOH.<ref>{{Cite web |last=PubChem |title=4-Iodobenzoic acid |url=https://pubchem.ncbi.nlm.nih.gov/compound/4-Iodobenzoic-acid |access-date=2023-01-21 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
+'''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|4-iodobenzoic acid crystallization<ref name="solidstate"/>]]
+[[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]] |url=https://doi.org/10.1021/jp047189b |volume=109 |issue=11 |pages=2586–2593 |doi=10.1021/jp047189b}}</ref>
+[[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==
@@ Line 58: / Line 55: @@
 ==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]] |url=https://doi.org/10.1039/B714160B |issue=31 |pages=3672–3674 |doi=10.1039/B714160B}}</ref>
+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>
-==See also==
-*[[2-Iodobenzoic acid]]
 ==References==
@@ Line 68: / Line 62: @@
 {{DEFAULTSORT:Iodobenzoic acid, 4-}}
 [[Category:Benzoic acids]]
-[[Category:Iodoarenes]]
+[[Category:4-Iodophenyl compounds]]