Asmic
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| Names | |
|---|---|
| Preferred IUPAC name
1-[(Isocyanomethyl)sulfanyl]-2-methoxybenzene | |
| Other names
Asmic; Anisyl sulfanyl methyl isocyanide | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.402.334 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C9H9NOS | |
| Molar mass | 179.24 g·mol−1 |
| Appearance | white solid |
| Melting point | 27 °C (81 °F; 300 K) |
| Solubility in polar organic solvents | Soluble |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| H301, H311, H315, H319, H331, H335 | |
| P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, 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).
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Anisyl sulfanyl methyl isocyanide (Asmic) is an organic compound with the formula CH3OC6H4SCH2NC. The molecule contains an ortho-methoxy-phenyl sulfide group to which is attached the isocyanide. Asmic is used as a reagent for the synthesis of tri-substituted isocyanides. The compound is a colorless although samples can appear off-white.[2][3]
Preparation and reactions
[edit]Asmic is prepared by dehydration of the corresponding formamide by POCl3.[4][5]
Asmic can be deprotonated at the methylene adjacent to the isocyanide. The anionic form of Asmic, which is stable at low temperatures, can be alkylated with a variety of electrophiles. Two sequential deprotonation-alkylation reactions and a subsequent sulfur-lithium exchange reaction allow the synthesis of tri-substituted isocyanides.[4]
The ortho-methoxy-phenyl sulfide group is thought to facilitate deprotonation by chelating to metalated bases allowing for the base to achieve optimal trajectory during the deprotonation.[4]
Asmic can be used to prepare oxazoles by condensation reactions with esters. The ortho-methoxy-phenyl sulfide group can also undergo sulfur-lithium exchange, and likely proceeds via a 10-s-3 sulfuranide.
Related compounds
[edit]References
[edit]- ↑ "1-[(Isocyanomethyl)sulfanyl]-2-methoxybenzene". pubchem.ncbi.nlm.nih.gov.
- ↑ Zhu, Jieping; Tron, Gian Cesare; Novellino, Ettore; Massarotti, Alberto; Mercalli, Valentina; Basso, Andrea; Giustiniano, Mariateresa (2017-03-06). "To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis". Chemical Society Reviews. 46 (5): 1295–1357. doi:10.1039/C6CS00444J. ISSN 1460-4744. PMID 27983738.
- ↑ "Molecule of the Week:asmic". C&E News. 2025.
- 1 2 3 Alwedi, Embarek; Lujan-Montelongo, J. Armando; Pitta, Bhaskar R.; Chao, Allen; Cortés-Mejía, Rodrigo; del Campo, Jorge M.; Fleming, Fraser F. (2018-09-21). "Asmic: An Exceptional Building Block for Isocyanide Alkylations". Organic Letters. 20 (18): 5910–5913. doi:10.1021/acs.orglett.8b02574. PMC 6172042. PMID 30188137.
- ↑ Shenvi, Ryan A.; Schnermann, Martin J. (2015-03-25). "Syntheses and biological studies of marine terpenoids derived from inorganic cyanide". Natural Product Reports. 32 (4): 543–577. doi:10.1039/C4NP00109E. PMC 4414506. PMID 25514696.