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 ;
ECHA InfoCard	100.002.852
PubChem CID	7672;
UNII	196GO6BSOH ;
CompTox Dashboard (EPA)	DTXSID5051521 ;
	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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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

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.

External links

Phenyl Isocyanate Data Sheet

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[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.