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Phenyl isocyanate is used with triethylamine in order to activate nitro groups to undergo 1,3-dipolar cycloaddition. It is also employed in the preparation of chemically modified cellulose paper. Further, it is used in the preparation of functionalized graphene oxide nanoplatelets. In addition to this, it reacts with ethyl alcohol to prepare ethyl alfa,gamma-diphenylallophanate and small amount of phenyl isocyanate dimer.
For general reactions of isocyanates, see Appendix 3.
Can be used, in the presence of pyridine, to protect alcohols as N-phenylcarbamates: J. Am. Chem. Soc., 94, 3578 (1972), e.g. selective protection of primary OH groups in pyranosides; cleavage by reduction with LiAlH4: Tetrahedron Lett., 28, 4165 (1987). The group can also be cleaved by refluxing with NaOMe: Acta Chem. Scand., 15, 87, 96 (1961). Amines may also be protected as N-phenylcarbamates: Tetrahedron Lett., 1935 (1977).
Forms ureas by reaction with amines; e.g. Tris(2-aminoethyl)amine, B21789, gives a molecule containing three urea groups which was used in studies of spacers for phosphate receptors: Chem. Lett., 759 (1995). Reaction with 4-aminobenzimidazole derivatives has been used in the synthesis of 1-phenylxanthine derivatives: Synthesis, 855 (1995).
In the presence of triethylamine, dehydrates nitroalkanes to nitrile oxides, which can undergo 1,3-dipolar cycloadditions: J. Am. Chem. Soc., 82, 5339 (1960); Synthesis, 757 (1980). Similarly, aldoximes are converted to nitriles: J. Org. Chem., 26, 782 (1961).
Conversion to diphenylcarbodiimide can be catalyzed by 3-Methyl-1-phenyl-2-phospholene 1-oxide, A11792: Org. Synth. Coll., 5, 501 (1973).
Seifi, M.; Ebrahimipour, S. Y.; Simpson, J.; Dusek, M.; Eigner, V.; Sheibani, H. Combination of Pyridinium and Isoquinolinium Ylides with Phenylisocyanate and Isothiocyanates: Synthesis, Characterisation, and X-Ray Crystal Structures of Mesoionic Monosubstituted 3-Oxo-Propanamides or Thioamides. Aust. J. Chem. 2015, 68 (10), 1577-1582.
Mali'n, T. J.; Lindberg, S.; Astot, C. Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance. J. Mass Spectrom. 2014, 49 (1), 68-79.
Mentions de danger (UE): H226-H302-H330-H314-H318-H334-H317
Flammable liquid and vapour. Harmful if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause an allergic skin reaction.
Mentions de prudence: P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.