Phenyl isocyanate

Phenyl isocyanate
Names
	Preferred IUPAC name Isocyanatobenzene
Identifiers
CAS Number	103-71-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53806 ;
ChemSpider	7389 ;
EC Number	203-137-6;
PubChem CID	7672;
UNII	196GO6BSOH ;
UN number	2487
	InChI InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H Key: DGTNSSLYPYDJGL-UHFFFAOYSA-N ;
	SMILES O=C=N/c1ccccc1;
Properties
Chemical formula	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)
Solubility in water	Reacts with water
Magnetic susceptibility (χ)	-72.7·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H302, H314, H317, H330, H334, H335, H410, H411
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P271, P272, P273, P280, P284, P301+317Script error: No such module "Preview warning".Category:GHS errors, P301+330+331, P302+352, P302+361+354Script error: No such module "Preview warning".Category:GHS errors, P303+361+353, P304+340, P305+354+338Script error: No such module "Preview warning".Category:GHS errors, P316Script error: No such module "Preview warning".Category:GHS errors, P317Script error: No such module "Preview warning".Category:GHS errors
	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.^[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 RCNO in the reaction, with CO₂ as one of the by products.^[3]

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

↑ "Phenyl isocyanate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/7672#section=Safety-and-Hazards.
↑ Emmanuil I. Troyansky "Phenyl Isocyanate" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons doi:10.1002/047084289X.rp073
↑ 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.
↑ 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.