4-Iodobenzoic acid

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

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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