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Organic-soluble borohydride. For references to reduction by borohydride, see Sodium borohydride, 35788. Changing the counter ion permits variation in reactivity and selectivity./n
Amides and nitriles are selectively reduced in dichloromethane: Heterocycles, 14, 1437, 1441 (1980); aryl ester, nitro or halo-substituents are unaffected. For the 1,4-reduction of enones, see: Tetrahedron, 37, 1171 (1981). Carboxylic acids can be reduced to alcohols by refluxing in DCM: Synth. Commun., 30, 941 (2000)./n
With reactive halides (e.g. MeI) in DCM, provides a convenient source of diborane: Tetrahedron Lett., 3173 (1972). Hydroboration of alkenes has also been effected by refluxing with the reagent in chloroform: Indian J. Chem., 37B, 1186 (1998)./n
Effective regent for cleavage of TMS ethers: Synth. Commun., 26, 1065 (1996)./n
Hazard Statements: H261-H314
In contact with water releases flammable gas. Causes severe skin burns and eye damage.
Precautionary Statements: P223-P231+P232-P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P335+P334-P363-P370+P378q-P501c
Keep away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. 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