物质信息
ID:716957
名称和标识
IUPAC标准名
1-isocyanomethanesulfonyl-4-methylbenzene
IUPAC传统名
TosMIC
别名
p-Toluenesulfonylmethyl isocyanide对甲苯磺酰甲基异腈TosMICp-Tolylsulfonylmethyl isocyanide
化合物性质
安全信息
安全公开号
36/37-45
TSCA收录
否
GHS危险品标识
急性毒性（口服，皮肤接触，吸入），类别1,2,3
GHS危险声明
H300-H311-H331
欧盟危险性物质标志
有毒 (T)危险公开号
23/24/25
保存注意事项
Moisture Sensitive
联合国危险货物等级
6.1
联合国危险货物包装类别(PG)
II
GHS警示性声明
P280H-P309-P310
联合国危险货物编号
UN2811
理化性质
熔点
109-114°C
产品相关信息
纯度
97+%
描述信息
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分子图谱
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参考文献
• Other applications in heterocyclic synthesis include the synthesis of:
• 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):
• 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:
• 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).
• 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).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 363 (2005).