Names | |
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Preferred IUPAC name Methyl 4-iodobenzoate | |
Other names Methyl p-iodobenzoate | |
Identifiers | |
CAS Number | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.009.635 |
EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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Properties | |
Chemical formula | C8H7IO2 |
Molar mass | 262.046 g·mol |
Appearance | white solid |
Melting point | 114 °C (237 °F; 387 K) |
Hazards | |
GHS labelling: | |
Pictograms | |
Signal word | Warning |
Hazard statements | H315, H319, H335, H411 |
Precautionary statements | P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, P501 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references |
Methyl 4-iodobenzoate, or methyl p-iodobenzoate, is an organic compound with the formula IC6H4COOCH3. It is the methyl ester of 4-iodobenzoic acid, or may also be viewed as an iodinated derivative of methyl benzoate.
Preparation
Methyl 4-iodobenzoate may be prepared by the Fischer esterification of 4-iodobenzoic acid with methanol.
Reactions
The aryl-iodide functionality of methyl 4-iodobenzoate may undergo coupling reactions, such as a symmetrical Sonogashira coupling with trimethylsilylacetylene (with the TMSA deprotected to acetylene in situ) to form dimethyl 4,4'-(ethyne-1,2-diyl)dibenzoate.
References
- "Methyl 4-iodobenzoate". ChemSpider. Retrieved 24 October 2023.
- "Methyl 4-iodobenzoate". pubchem.ncbi.nlm.nih.gov.
- PubChem. "Methyl 4-iodobenzoate". PubChem. Retrieved 24 October 2023.
- ^ 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.
- Mio, Matthew J.; Kopel, Lucas C.; Braun, Julia B.; Gadzikwa, Tendai L.; Hull, Kami L.; Brisbois, Ronald G.; Markworth, Christopher J.; Grieco, Paul A. (2002). "One-Pot Synthesis of Symmetrical and Unsymmetrical Bisarylethynes by a Modification of the Sonogashira Coupling Reaction". Organic Letters. 4 (19): 3199–3202. doi:10.1021/ol026266n. PMID 12227748.