tert-Butyl iodide
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| Names | |||
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| Systematic IUPAC name
2-Iodo-2-methylpropane | |||
| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.008.356 | ||
| EC Number |
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PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C4H9I | |||
| Molar mass | 184.020 g·mol−1 | ||
| Density | 1.5445 g·cm−3[1] | ||
| Melting point | −38.2 °C (−36.8 °F; 235.0 K) | ||
| Boiling point | 100.1 °C (212.2 °F; 373.2 K) | ||
| Hazards | |||
| GHS labelling:[1] | |||
| Danger | |||
| H225, H315, H319, H335, H400 | |||
| P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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tert-Butyl iodide (systematic name 2-iodo-2-methylpropane) is an organoiodine compound with the formula Me3CI (Me = methyl). The molecule features a tert-butyl group attached to a iodide substituent.
This chemical is used as a precursor for the tert-butyl radical in various organic chemical reactions.[2][3] It can also serve as an electrophile in many types of reactions. Examples include for conversion of amino acids to their tert-butyl esters under mild conditions,[4] Heck reactions[5] and electrophilic aromatic substitutions.[6] In combination with DMSO and an additional oxidizing agent such as iodine, it can convert aryl-methyl groups to the corresponding aryl aldehydes.[7][8] The reaction is postulated to proceed via generation of an intermediate alkoxysulfonium species.[9]
References
- ^ Audsley, Arnold; Goss, Frank R. (1942). "59. The magnitude of the solvent effect in dipole-moment measurements. Part V. The solvent-effect constant and the moments of alkyl iodides". Journal of the Chemical Society (Resumed): 364. doi:10.1039/JR9420000358.
- ^ Miyabe, Hideto; Ueda, Masafumi; Naito, Takeaki (2000). "N-Sulfonylimines as an excellent acceptor for intermolecular radical reactions". Chemical Communications (20): 2059–2060. doi:10.1039/B006574I.
- ^ Ma, Gaoyuan; Fujita, Takehiro; Sibi, Mukund P. (2015). "Lewis acid mediated diastereoselective intermolecular radical addition/Trapping with pyrazolidinone acrylimides". Tetrahedron Letters. 56 (23): 3571–3574. doi:10.1016/j.tetlet.2015.02.008.
- ^ Anderson, George W.; Callahan, Francis M. (1960). "T-Butyl Esters of Amino Acids and Peptides and their Use in Peptide Synthesis1". Journal of the American Chemical Society. 82 (13): 3359–3363. Bibcode:1960JAChS..82.3359A. doi:10.1021/ja01498a032.
- ^ Kurandina, Daria; Rivas, Mónica; Radzhabov, Maxim; Gevorgyan, Vladimir (2018). "Heck Reaction of Electronically Diverse Tertiary Alkyl Halides". Organic Letters. 20 (2): 357–360. doi:10.1021/acs.orglett.7b03591. PMC 5813498. PMID 29303271.
- ^ Fu, Wanting; Tian, Jing; Ding, Yuanli; Wang, Xi; Wang, Meiyan; Wang, Zikun (2024). "Copper-Catalyzed Site-Selective Electrophilic Aromatic Alkylation of Monosubstituted Simple Arenes". Organic Letters. 26 (13): 2546–2551. doi:10.1021/acs.orglett.4c00475. PMID 38522077.
- ^ Vismara, Elena; Fontana, Francesca; Minisci, Francesco (1987). "A new method for the oxidation of methyl to formyl groups in heteroaromatic derivatives". Gazzetta Chimica Italiana. 117 (2): 135–136.
- ^ Queffélec, Clémence; Pati, Palas Baran; Pellegrin, Yann (12 June 2024). "Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions" (PDF). Chemical Reviews. 124 (11): 6766–6767, 6772. doi:10.1021/acs.chemrev.3c00543. PMID 38747613.
- ^ Vismara, Elena (January 1988). "A new type of functionalization of the benzylic-type positions in alkylpyridines by DMSO-Ac2O". Tetrahedron Letters. 29 (36): 4619–4622. doi:10.1016/S0040-4039(00)80563-8.