Phenethyl isocyanate
[CAS# 1943-82-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanate ester / isocyanate
• Name: Phenethyl isocyanate
• Synonyms: 2-isocyanatoethylbenzene
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• CAS Registry Number: 1943-82-4
• EC Number: 413-080-0
• SMILES: C1=CC=C(C=C1)CCN=C=O

Properties

• Water solubility: decomposes (Expl.)
• Density: 1.0±0.1 g/cm³, Calc.^*, 1.063 g/mL (Expl.)
• Index of Refraction: 1.514, Calc.^*, 1.522 (Expl.)
• Boiling Point: 228.5±19.0 °C (760 mmHg), Calc.^*, 210 °C (Expl.)
• Flash Point: 67.4±22.6 °C, Calc.^*, 99 °C (Expl.)

Safety Data

• Hazard Symbols: GHS06;GHS08;GHS05;GHS09 Danger
• Risk Statements: H331-H302-H314-H334-H317-H411
• Safety Statements: P233-P260-P261-P264-P270-P271-P272-P273-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P330-P333+P317-P342+P316-P362+P364-P363-P391-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H331
Skin corrosion	Skin Corr.	1A	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1	H314

• Transport Information: UN 2206

Discovery and Applications

Phenethyl isocyanate is an organic compound that belongs to the class of isocyanates, characterized by the presence of the -N=C=O functional group. Its molecular structure, featuring a phenethyl moiety bonded to the reactive isocyanate group, makes it a versatile building block in chemical synthesis. The compound is represented by the formula C9H9NO, and its discovery traces back to investigations into reactive intermediates for polymer and pharmaceutical applications.

Phenethyl isocyanate has been extensively studied for its role in organic synthesis, particularly in the preparation of ureas, carbamates, and related compounds. The isocyanate group readily reacts with nucleophiles, such as amines and alcohols, enabling the formation of diverse functional products. These reactions are critical in producing polymers, agrochemicals, and pharmaceutical intermediates.

The compound is also of interest in medicinal chemistry. Phenethyl derivatives are known for their biological activities, and phenethyl isocyanate itself has been explored for potential anticancer and antimicrobial properties. Research has shown that isocyanates can induce apoptosis in cancer cells, partly through interactions with cellular proteins. Phenethyl isocyanate, in particular, has been evaluated for its selective cytotoxicity and ability to modulate oxidative stress in cancer models.

Industrial applications of phenethyl isocyanate include its use in polymer chemistry. Its reactivity makes it suitable for creating polyurethanes and other materials with tailored properties. The phenethyl group enhances the hydrophobicity and rigidity of the resulting polymers, making them suitable for coatings, adhesives, and insulation materials.

Safety considerations are critical in handling phenethyl isocyanate, as isocyanates are known to be irritants and sensitizers. Proper precautions, including the use of protective equipment and adequate ventilation, are essential during its synthesis and application to mitigate risks associated with exposure.

References

2024. Creep-Resistant Covalent Adaptable Networks with Excellent Self-Healing and Reprocessing Performance via Phase-Locked Dynamic Covalent Benzopyrazole-Urea Bonds. Chinese Journal of Polymer Science, 42(8).
DOI: 10.1007/s10118-024-3195-4

2013. The Inactivation of Human CYP2E1 by Phenethyl Isothiocyanate, a Naturally Occurring Chemopreventive Agent, and Its Oxidative Bioactivation. Drug Metabolism and Disposition, 41(4).
DOI: 10.1124/dmd.112.050609

200 NAN. 1-Phenylethyl isocyanate is a powerful reagent for the chiral analysis of secondary alcohols and hydroxy fatty acids with remote stereogenic centres. Journal of Chromatography A, 1167(2).
DOI: 10.1016/j.chroma.2007.07.051