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Methylmagnesium chloride is a source of methyl anion, and widely used as an alkylating agent. It readily adds the methyl anion across the carbonyl group of aldehydes, ketones and esters. It can also be used as a strong base in aprotic solvents.
Vollmer, G. Y.; Wallasch, M. W.; Saurenz, D.; Eger, T. R.; Bauer, H.; Wolmershäuser, G.; Prosenc , M. H.; Sitzmann, H. Benzylidyne Bridges from Diphenylacetylene and a Methylidyne Bridge from Methylmagnesium Chloride. Organometallics 2015, 34 (3), 644-652.
Bailey, C. L.; Clary, J. W.; Tansakul, C.; Klabunde, L.; Anderson, C. L.; Joh, A. Y.; Lill, A. T.; Peer, N.; Braslau, R.; Singaram, B. Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents. Tetrahedron Lett. 2015, 56 (5), 706-709.
Hazard Statements: H225-H260-H314-H335-H336-H351
Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. Causes severe skin burns and eye damage. May cause respiratory irritation. May cause drowsiness or dizziness. Suspected of causing cancer.
Precautionary Statements: P201-P202-P210-P223-P231+P232-P233-P235-P240-P241-P242-P243-P260-P264b-P271-P281-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P335+P334-P363-P370+P378q-P501c
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 away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. 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 Use only outdoors or in a well-ventilated area. Use personal protective equipment as required. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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. Immediately call a POISON CENTER or doctor/physician. Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant