55887-59-7

Basic information

• Product Name: 1-Phenylallyl isocyanate
• Synonyms: (1-Isocyanato-2-propenyl)benzene;1-Phenyl-2-propenyl isocyanate;1-Phenylallyl isocyanate
• CAS NO: 55887-59-7
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 0
• Mol File: 55887-59-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Phenylallyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylallyl isocyanate(55887-59-7)
• EPA Substance Registry System: 1-Phenylallyl isocyanate(55887-59-7)

Safety Data

• Hazardous Substances Data: 55887-59-7(Hazardous Substances Data)

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

• 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 
• 1078-70-2 3-phenylprop-2-enyloxycarbonylamine 
• 29771-28-6 hydrazinecarbothioic acid O-(3-phenyl-allyl) ester 

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 articles and documents

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.

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.