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
EC Number	203-137-6;
PubChem CID	7672;
UNII	196GO6BSOH ;
UN number	2487
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
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H314, H317, H330, H334, H335, H410, H411
Precautionary statements	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). 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.^[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

^ "Phenyl isocyanate". pubchem.ncbi.nlm.nih.gov.
^ 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

[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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