イソシアン酸 ベンジル

外観

無色～うすい黄色～うすい黄赤色透明液体

溶解性

エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。

用途

有機合成用試薬。

化学的特性

CLEAR COLOURLESS TO FAINTLY YELLOW LIQUID

天然物の起源

benzyl isocyanate is a natural product found in Simicratea welwitschii with data available.?

使用

Benzyl isocyanate, is used as a protected ammonia equivalent in the stereo selective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate. It is also used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex.

一般的な説明

Benzyl isocyanate inhibits the formation of benzo[a]pyrene (BP)-DNA adduct and posses chemopreventive properties.

合成

The conversion of benzyl azide to benzyl isocyanate (Scheme 1) was selected as the model reaction and it was performed both under conventional conditions and under MW irradiation. Various solvents were compared at a number of temperatures thanks to the versatility of the SynthWave reactor, which provides multiple-sample racks. Experiments were performed at 90, 70 and 50 °C at 14.5 bar of CO2 pressure.

Scheme 1: Synthesis of benzyl isocyanate.
One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger–aza-Wittig reaction