Phenyl isocyanate

• Catalog No.: A12808
• CAS Number: 103-71-9
• M. F.: C7H5NO
• M. W.: 119.1207
• Purity: 98+%

SYNONYMS

• Title: 异氰酸苯酯
• IUPAC name: isocyanatobenzene
• IUPAC Traditional name: phenyl isocyanate

DATABASE IDS

• Merck Index: 147296
• Beilstein Number: 471391
• EC Number: 203-137-6
• MDL Number: MFCD00001994
• CAS Number: 103-71-9

PROPERTIES

• Purity: 98+%
• Boiling Point: 62-64°C/11mm
• Density: 1.094
• Flash Point: 51°C(123°F)
• Melting Point: -33°C
• Refractive Index: 1.5360
• GHS Hazard statements: H301-H330-H317-H334-H314-H318-H226
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A
• Risk Statements: 10-22-26-34-42/43
• RTECS: DA3675000
• Safety Statements: 23-26-28-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2487
• Packing Group: I

REFERENCES

• 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).