4-Iodobenzoic acid

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

4-Iodobenzoic acid

Names
Preferred IUPAC name 4-Iodobenzoic acid
Other names p-Iodobenzoic acid
Identifiers
CAS Number	619-58-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL101265
ChemSpider	11588 Y
ECHA InfoCard	100.009.641
EC Number	210-603-2
PubChem CID	12085
UNII	IPO4LYQ1EN Y
CompTox Dashboard (EPA)	DTXSID20862304
InChI InChI=1S/C7H5IO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10) Y Key: GHICCUXQJBDNRN-UHFFFAOYSA-N Y
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)[1]
Hazards
GHS labelling:[2]
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). Y verify (what is YN ?) Infobox references

Structure

4-iodobenzoic acid crystallization^[4]

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]