54838-77-6

Usage

Physical properties

colorless liquid with a mild, sweet odor

Uses

fragrance ingredient in personal care and household products, chiral ligand in asymmetric hydrogenation reactions, production of pharmaceuticals and fine chemicals

Toxicity

considered to have low toxicity and not expected to pose significant health risks

Safety guidelines

should be used in accordance with safety guidelines

Upstream product

• 848617-96-9 (+/-)-B-allenyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 
• 90-82-4 rac-pseudoephedrine 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 460752-23-2 6-dimethylphenylsilyl-2-methyl-3-(2-tetrahydropyranyloxy)-5-hexyne 
• 460752-54-9 (E)-6-bromo-6-dimethylphenylsilyl-2-methyl-3-(2-tetrahydropyranyloxy)-5-hexene 
• 460752-88-9 (Z)-6-dimethylphenylsilyl-2-methyl-5-decen-3-ol 
• 55049-25-7 (E)-2-methyl-6-phenylhex-5-en-3-ol 

Relevant academic research and scientific papers

Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) The asymmetric allenylboration of representative aldehydes with the stable, storable 1 is reported. Easily and efficiently prepared in either enantiomeric form from the air-stable crystalline 4 through simple Grignard procedures, 1 gives 6 cleanly. The latter is easily isolated in high yield and ee with predictable stereochemistry. The procedure also regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine. The net process is the synthetic equivalent of the asymmetric addition of allenylmagnesium bromide to aldehydes.