Phenyl isocyanate

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Phenyl isocyanate
Phenylisocyanate.svg
Phenyl-isocyanate-3D-balls.png
Names
Preferred IUPAC name
Isocyanatobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.852 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-137-6
PubChem CID
UNII
UN number 2487
  • InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H Yes check.svgY
    Key: DGTNSSLYPYDJGL-UHFFFAOYSA-N Yes check.svgY
  • O=C=N/c1ccccc1
Properties
C7H5NO
Molar mass 119.123 g·mol−1
AppearanceColourless 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
Hazards
GHS labelling: [1]
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H226, H302, H314, H317, H330, H334, H335, H410, H411
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P342+P316, P362+P364, P363, P370+P378, P391, P403, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Characteristic of other isocyanates, it reacts with amines to give ureas. [2] 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 oxime-like dimers in the reaction: [3]

4 PhNCO + 2 RCH2NO2 → 2(PhNH)2CO + 2 CO2 + (RCNO)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. [4]

References

  1. ↑ "Phenyl isocyanate". pubchem.ncbi.nlm.nih.gov.
  2. ↑ Emmanuil I. Troyansky "Phenyl Isocyanate" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons doi : 10.1002/047084289X.rp073
  3. ↑ 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.
  4. ↑ 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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