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Benzyl isocyanate, is used as a protected ammonia equivalent in the stereo selective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate. It is also used in a multicomponent, stereospecific synthesis of 1,3-oxazinane-2,4-diones employing an Al-salph complex.
LL Ferstandig.; RA Scherrer. Mechanism of Isocyanate Reactions with Ethanol1. J. Am. Chem. Soc. 195981(18) , 4838-4842.
DG Hoare.; DE Koshland Jr. A procedure for the selective modification of carboxyl groups in proteins. J. Am. Chem. Soc. 196688(9) , 2057-2058.
Protected ammonia equivalent in the stereoselective ring-opening of chiral 2,3-epoxy alcohols (from Sharpless asymmetric epoxidation). The key step in the sequence involves intramolecular cyclization of the carbamate intermediate: J. Org. Chem., 50, 3752 (1985):
For general reactions of isocyanates, see Appendix 3.
Hazard Statements: H226-H301-H311-H315-H317-H319-H331-H334-H335
Flammable liquid and vapour. Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye irritation. Toxic if inhaled. May cause allergy or asthma symptoms or breathing difficulties if inhaled. May cause respiratory irritation.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P270-P271-P272-P280-P285-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P311-P312-P330-P333+P313-P337+P313-P363-P370+P378q-P50
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. In case of inadequate ventilation wear respiratory protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam