55887-59-7

Usage

Classification

Organic isocyanate

Structural components

Contains a phenyl and an allyl group

Reactivity

Highly reactive compound

Uses

Commonly used in organic synthesis to introduce the isocyanate functional group into various molecules; utilized in the production of polyurethane and other polymers

Odor

Strong, pungent odor

Hazards

Potential to cause irritation to the skin, eyes, and respiratory system; considered to be hazardous to the environment and should be disposed of properly.

Upstream product

• 29771-28-6 hydrazinecarbothioic acid O-(3-phenyl-allyl) ester 
• 1078-70-2 3-phenylprop-2-enyloxycarbonylamine 
• 104-54-1 3-Phenylpropenol 
• 59016-54-5 1-cyano-4-N,N-dimethylaminopyridinium bromide 
• 1027911-01-8 (2,2,2-Trichloro-acetyl)-carbamic acid (E)-3-phenyl-allyl ester 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 86766-60-1 Methyl N-(1-phenylprop-2-enyl)carbamate 
• 103-40-2 succinic acid monobenzyl ester 
• 91230-13-6 benzyl N-(1-phenylallyl)carbamate 

Relevant academic research and scientific papers

Further development of the tin-catalyzed transcarbamoylation reaction

Studies carried out to further develop tin-catalyzed trans-carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates.

Preparation of rearranged allylic isocyanates from the reaction of allylic alcohols with 1-Cyano-4-dimethylaminopyridinium bromide

A shorter and less costly alternative to Ichikawa's [1,3]-Transposition protocol for cyanates to isocyanates is described.

The first direct observation of an allylic [3,3] sigmatropic cyanate-isocyanate rearrangement

Evidence is presented that the [3,3] sigmatropic rearrangement of simple allyl cyanates to give allyl isocyanates proceeds much more rapidly than the analogous reaction of propargyl cyanates. Nevertheless, a substituted allyl cyanate is isolated for the first time, and the activation parameters of its [3,3] sigmatropic isomerization are measured.

A new synthetic method for the preparation of amino sugars through an allyl cyanate-to-isocyanate rearrangement

A new approach for the synthesis of amino sugars using an allyl cyanate-to-isocyanate rearrangement has been developed. The key feature in this method involves introduction of the nitrogen substituent into the pyranose framework by [3,3] sigmatropic rearrangement of an allyl cyanate. Subsequent functionalization of the allylamine moiety by either hydroxylation or cyclofunctionalization completes the synthesis of two amino sugars, D-perosamine and D-vicenisamine.