Methyl 4-iodobenzoate
Names
Preferred IUPAC name
Methyl 4-iodobenzoate
Other names
Methyl p-iodobenzoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.635
EC Number
  • 210-597-1
  • InChI=1S/C8H7IO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,1H3 checkY
    Key: DYUWQWMXZHDZOR-UHFFFAOYSA-N checkY
  • COC(=O)C1=CC=C(C=C1)I
Properties
C8H7IO2
Molar mass 262.046 g·mol−1
Appearance white solid
Melting point 114 °C (237 °F; 387 K)[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H335, H411
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 [77 °F], 100 kPa).
Infobox references

Methyl 4-iodobenzoate, or methyl p-iodobenzoate, is an organic compound with the formula IC6H4COOCH3.[3] 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.[4]

Reactions

Dimethyl 4,4'-(ethyne-1,2-diyl)dibenzoate

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.[4][5]

References

  1. ↑ "Methyl 4-iodobenzoate". ChemSpider. Retrieved 24 October 2023.
  2. ↑ "Methyl 4-iodobenzoate". pubchem.ncbi.nlm.nih.gov.
  3. ↑ PubChem. "Methyl 4-iodobenzoate". PubChem. Retrieved 24 October 2023.
  4. 1 2 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.
  5. ↑ 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.
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