Chemistry:Phenyl isocyanate
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| Names | |
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| Preferred IUPAC name
Isocyanatobenzene | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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PubChem CID
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| UNII | |
| UN number | 2487 |
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| Properties | |
| 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) |
| Reacts with water | |
| -72.7·10−6 cm3/mol | |
| Hazards | |
| GHS pictograms |      
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| GHS Signal word | Danger |
| H226, H302, H314, H317, H330, H334, H335, H410, H411 | |
| 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). | |
 verify (what is   ?)
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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.
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