What molecule am I?
Asmic, short for o-anisylsulfanylmethyl isocyanide, is a relatively newly developed reagent for introducing the isocyanide (isonitrile) group in organic synthesis.
Asmic first came to light in 2015 in by Fraser Fergusson Fleming and Jes煤s Armando Lujan-Montelongo at Duquesne University (Pittsburgh). The first line in the applications reads, 鈥淭his invention relates to novel isonitriles, including arylthio isonitriles, and methods for their preparation.鈥�
In 2018, Fleming, now at Drexel University (Philadelphia), and co-workers followed up by describing Asmic as a . In particular, the authors found that the o-anisylsulfanyl group is critical for facilitating the initial deprotonation鈥揳lkylation step and providing a nucleophilic site for promoting the n-butyllithium1 removal of the sulfanyl moiety. The overall reaction can be used to synthesize methyl isocyanides with as many as three substituents.
In subsequent years, Fleming et al. expanded on the synthetic advantages of Asmic. In 2020, they reported that the reagent is useful for addition reactions with carbonyl compounds to . The reaction, which forms four new bonds, is mediated by the boron trifluoride鈥揹iethyl ether2 adduct.
Similarly, in 2023, the research group described of oxazoles from Asmic, an alkyl halide, and an acid chloride and of imidazoles from Asmic, an alkyl halide, and a nitrile. In both cases, the products can contain up to two substituents. The authors point out that 59% of US Food and Drug Administration鈥揳pproved small-molecule drugs contain nitrogen heterocycles such as can be produced by Asmic ring-forming reactions.
Currently, no hazard information is available for Asmic.
1. CAS Reg. No. 109-72-8.
2. CAS Reg. No. 109-63-7.
Winter Remedy Molecules
Elderberry tea is a traditional remedy for combatting the effects of colds and flu. The tea is made from dried flowers of the elderberry tree (Sambucus nigra), which contain a wide range of antioxidants, including anthocyanins, flavonoids, and phenolic acids.
The phenolic acids consist of former Molecule of the Week chlorogenic acid1, as well as its isomers neochlorogenic acid2 and cryptochlorogenic acid3. In 2017, Karolina M艂ynarczyk, Dorota Walkowiak-Tomczak, and Grzegorz P. 艁ysiak* at the Poznan University of Life Sciences (Poland), wrote a comprehensive treatise on the as ingredients in foods and pharmaceuticals. In particular, the authors focused on the mechanisms that the chlorogenic acids and other compounds reduce the symptoms of wintertime maladies.
1. CAS Reg. No. 327-97-9.
2. CAS Reg. No. 906-33-2.
3. CAS Reg. No. 905-99-7.
Winter Remedy Molecules
Throughout January, MOTW will feature key components of natural substances that people use when they have coughs or runny noses.鈥擡d.聽See this week's winter remedy.
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Asmic聽fast facts
| CAS Reg. No. | 1803329-89-6 |
| SciFindern name | Benzene, 1-[(isocyanomethyl)thio]-2-methoxy- |
| Empirical formula | C9H9NOS |
| Molar mass | 179.24 g/mol |
| Appearance | White to off-white solid |
| Melting point | 27 潞C |
| Water solubility | Not reported |
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