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36635-61-7 - p-Toluenesulfonylmethyl isocyanide, 97+% - p-Tolylsulfonylmethyl isocyanide - TosMIC - A14312 - Alfa Aesar

A14312 p-Toluenesulfonylmethyl isocyanide, 97+%

CAS-Nummer
36635-61-7
Synonyme
p-Tolylsulfonylmethyl isocyanide
TosMIC

Größe Preis ($) Menge Verfügbarkeit
5g 30,32
25g 114,06
100g 370,40
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p-Toluenesulfonylmethyl isocyanide, 97+%

MDL
MFCD00000005
EINECS
253-140-1

Chemische Eigenschaften

Formel
C9H9NO2S
Molmasse
195.24
Schmelzpunkt
109-114°
Sensitivität
Moisture Sensitive
Löslichkeit
Soluble in chloroform and methanol. Insoluble in water.

Anwendungen

p-Toluenesulfonylmethyl isocyanide is a synthetic reagent used in the synthesis of triplet drugs with the 1,3,5-trioxazatriquinane skeleton, pyrroles, oxazoles and in imidazoles. It serves as an isonitrile component in a diastereoselective Passerini reaction. Furthermore, it is used in the Van Leusen reaction to convert aldehydes to nitriles.

Bemerkungen

Moisture, air and light sensitive. Store in cool place. Incompatible with strong bases and strong oxidizing agents.

Literaturverweise

Successive alkylation with different alkyl groups, followed by acid hydrolysis, leads to unsymmetrical ketones: Tetrahedron Lett., 4229 (1977). Similarly, dialkylation with ɑω-dihalides gives cyclobutanones: Synthesis, 325 (1980), or larger-ring ketones: Tetrahedron Lett., 22, 4193 (1981). Reaction of monoalkylated TosMIC with ɑω-dihalides is a useful route to 1,5- or 1,6-diketones: Rec. Trav. Chim., 104, 50 (1985):

In the presence of base (e.g. KO-t-Bu) in an aprotic solvent, e.g. DME, ketones are cyanated to give the homologous nitriles; see, e.g.: Org. Synth. Coll., 6, 41 (1988). Hindered ketones can be cyanated in DMSO: J. Org. Chem., 42, 3114 (1977). Aldehydes condense with TosMIC at -50o, followed by hydrolysis in refluxing methanol: Synth. Commun., 10, 399 (1980).

In contrast, aldehydes with K2CO3 in refluxing methanol lead to high yields of 5-substituted oxazoles: Tetrahedron Lett., 2369 (1972); with acid chlorides, the corresponding 4-tosyl oxazoles are obtained. For asymmetric induction in the oxazole synthesis by use of π-arylaldehyde-chromium tricarbonyl complexes, see: Tetrahedron: Asymmetry, 3, 287 (1992).

Other applications in heterocyclic synthesis include the synthesis of:

Imidazoles by reaction with imidoyl chlorides: Tetrahedron Lett., 2373 (1972). Thiazoles by reaction with CS2 under phase-transfer conditions: Synthesis, 501 (1977). 1,2,4-Triazoles by reaction with diazonium salts, and pyrroles by reaction with Michael acceptors: Tetrahedron Lett., 5337 (1972). Pyrroles are also formed by reaction with aldehydes followed by either ethyl cyanoacetate to give 3-cyanopyrroles: J. Org. Chem., 57, 2245 (1992), or nitromethane to give 3-nitropyrroles: Tetrahedron, 47, 4639 (1991); Synthesis, 871 (1996). The same products are also obtained by reaction of TosMIC with nitroalkenes, from Henry reaction of the aldehydes with nitromethane:

For a brief feature on uses of the reagent in synthesis, see: Synlett, 363 (2005).

Bano, H.; Yousuf, S. Crystal structure of p-toluenesulfonylmethyl isocyanide. Acta Crystallogr. Sect. A 2015, 71 (6), 0412-0412.

Murale, D. P.; Hong, S. C.; Yun, J.; Yoon, C. N.; Lee, J. S. Rational design of a photo-crosslinking BODIPY for in situ protein labeling. Chem. Commun. 2015, 51 (30), 6643-6646.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H300-H311-H331

Fatal if swallowed. Toxic in contact with skin. Toxic if inhaled.

Sicherheitshinweise: P280h-P309-P310

Wear protective gloves/clothing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Weitere Referenzen

Beilstein
3592382
Gefahrenklasse
6.1
Verpackungsgruppe
II
Harmonized Tariff Code
2930.90
TSCA
No

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