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Allyl chloride is used as an alkylating agent. It is used in treatment with sodium bis(trimethylsilyl)amide gives the strained, highly reactive alkene cyclopropene.
Kenji Uneyama.; Nobuyoshi Kamaki.; Akihiko Moriya.; Sigeru Torii. Tin(II)-aluminum-promoted allylation of aldehydes with allyl chloride in an aqueous solvent system. J. Org. Chem. 1985, 50 (25), 5396-5399.
Farley Fisher.; Douglas E. Applequist. Synthesis of 1-Methylcyclopropene. J. Org. Chem. 1965, 30 (6), 2089-2090.
Lithiation with LDA in THF at -78o generatesɑ-chloroallyllithium which can be ɑ-alkylated with primary bromides in high yield. Displacement of the resulting allylic chloride with a dialkyl cuprate to give, stereoselectively, an (E)-alkene, has been used in a pheromone synthesis: J. Org. Chem., 45, 1504 (1981).
Treatment with sodium bis(trimethylsilyl)amide gives the strained, highly reactive alkene cyclopropene. For details and Diels-Alder reactions, see: J. Org. Chem., 61, 6462 (1996).
Hazard Statements: H225-H302-H312-H315-H319-H332-H335-H341-H351-H373
Highly flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Harmful if inhaled. May cause respiratory irritation. Suspected of causing genetic defects. Suspected of causing cancer. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P201-P202-P210-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280i-P281-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P308+P313-P312-P330-P332+P313-P337+P313-P363-P37
Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. 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. Do not breathe 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. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. 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. IF exposed or concerned: Get medical advice/attention. Rinse mouth. If skin irritation occurs: If eye irritation persists: Wash contaminated clothing before reuse.