Phenyl isocyanate

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 is therefore handled with care.

Phenyl isocyanate
Names
Preferred IUPAC name
Isocyanatobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.852
UNII
Properties
C7H5NO
Molar mass 119.123 g·mol−1
Appearance Colourless liquid
Density 1.09
Melting point -30 °C
Boiling point 165 °C
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

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]

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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: 5339. 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: 9480–9497. doi:10.1021/ja00074a013.CS1 maint: uses authors parameter (link)
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