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103-71-9 - Phenyl isocyanate, 98+% - A12808 - Alfa Aesar

A12808 Phenyl isocyanate, 98+%

Número CAS
103-71-9
Nombre Alternativo

Tamaño Precio ($) Cantidad Disponibilidad
5g 19,40
100g 31,40
250g 62,10
1000g 197,00
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Phenyl isocyanate, 98+%

MDL
MFCD00001994
EINECS
203-137-6

Propiedades químicas

Fórmula
C7H5NO
Peso molecular
119.12
Punto de fusión
-33°
Punto de ebullición
62-64°/11mm
Punto de inflamabilidad
51°(123°F)
Densidad
1.094
Índice de refracción
1.5360
Sensibilidad
Moisture Sensitive
Solubilidad
Miscible with ether.

Aplicaciones

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.

Notas

Store in a cool place. Incompatible with strong oxidizing agents, water, moisture, alcohols, amines, strong bases and strong acids.

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H330-H302-H317-H334-H314-H318-H226

Fatal if inhaled. Harmful if swallowed. May cause an allergic skin reaction. May cause allergy or asthma symptoms or breathing difficulties if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Flammable liquid and vapour.

Indicaciones de precaución: P210-P260-P284-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. 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). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Merck
14,7296
Beilstein
471391
Clase de peligro
6.1
Grupo de embalaje
I
Código de tarifa arancelaria unificado
2929.10
TSCA
Yes
RTECS
DA3675000

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