4-Iodobenzoic acid
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| Names | |
|---|---|
| Preferred IUPAC name 4-Iodobenzoic acid | |
| Other names p-Iodobenzoic acid | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.009.641 |
| EC Number |
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PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| Properties | |
| 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] | |
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| Warning | |
| H315, H319, H335 | |
| 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). | |
4-Iodobenzoic acid, or p-iodobenzoic acid, is an isomer of iodobenzoic acid.[3]
Structure
[edit]
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
[edit]4-Iodobenzoic acid may be prepared in the laboratory by the oxidation of p-iodotoluene with potassium permanganate.[5]
Reactions
[edit]The carboxylic acid functionality of 4-iodobenzoic acid undergoes Fischer–Speier esterification with methanol to form the ester methyl 4-iodobenzoate.[6]
References
[edit]- ^ "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.