Phenyl isocyanate
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Isocyanatobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.852
UNII
  • InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H checkY
    Key: DGTNSSLYPYDJGL-UHFFFAOYSA-N checkY
  • O=C=N/c1ccccc1
Properties
C7H5NO
Molar mass 119.123 g·mol−1
Appearance Colourless liquid
Density 1.09
Melting point −30 °C (−22 °F; 243 K)
Boiling point 165 °C (329 °F; 438 K)
Reacts with water
-72.7·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenyl isocyanate is an organic compound typically abbreviated PhNCO. The molecule consists of a phenyl ring attached to the isocyanate functional group. It is a colourless liquid that reacts with water. Phenyl isocyanate has a strong odor and tearing vapours, therefore it has to be handled with care.

Characteristic of other isocyanates, it reacts with amines to give ureas.[1] Similarly, reacts with alcohols to form carbamates.

It is used in addition with triethylamine to activate nitro groups to undergo (C,O) 1,3-dipolar cycloaddition (as opposed to O,O). The nitro group (RCH2NO2) is converted to RCNO in the reaction, with CO2 as one of the by products.[2]

Structure

PhNCO is a planar molecule, according to X-ray crystallography. The N=C=O linkage is nearly linear. The C=N and C=O distances are respectively 1.195 and 1.173 Å.[3]

References

  1. ↑ Emmanuil I. Troyansky "Phenyl Isocyanate" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons doi:10.1002/047084289X.rp073
  2. ↑ Mukaiyama, Teruaki; Hoshino, Toshio (1960). "The Reactions of Primary Nitroparaffins with Isocyanates". Journal of the American Chemical Society. 82 (20): 5339–5342. doi:10.1021/ja01505a017.
  3. ↑ Marianne P. Byrn; Carol J. Curtis; Yu Hsiou; Saeed I. Khan; Philip A. Sawin; S. Kathleen Tendick; Aris Terzis; Charles E. Strouse (1993). "Porphyrin Sponges: Conservative of Host Structure in over 200 Porphyrin-Based Lattice Clathrates". J. Am. Chem. Soc. 115 (21): 9480–9497. doi:10.1021/ja00074a013.
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