3-pinanyl-9-borabicyclo[3.3.1]nonane, CAS No. 73624-47-2

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73624-47-2

Catalog No. EBD8919

CAS 73624-47-2

Name 3-pinanyl-9-borabicyclo[3.3.1]nonane

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Basic Information

Synonyms: 3-pinanyl-9-borabicyclo[3.3.1]nonane B-3-pinnanyl-9-borobicyclo<3.3.1>nonane B-3-pinanyl-9-borabicyclo<3.3.1>nonane B-3-pinanyl-9-boracyclo<3.3.1>nonane B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane B-3-pinanyl-9-borabicyclo[3.3.1]nonane B-Ipc-9-BBN R-alpine-borane (R)-2,6,6-trimethyl-4-(9-borabicyclo[3.3.1]nonan-9-yl)bicyclo[3.1.1]heptane R-2,7,7-trimethylnorpinanborabicyclo(3.3.1)nonane (R)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane 9-((2s,3r)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)-9-borabicyclo[3.3.1]nonane 9-[(1S,2S,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]-9-borabicyclo[3.3.1]nonane 9-[(1S,2S,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-

Molecular Formula: C18H31B

Molecular Weight: 258.25

MDL Number: MFCD00074776

Categories: Synthetic Chemistry > Catalysts and Ligands > Chiral Ligands Synthetic Chemistry > Basic Synthetic Reagents > Reducing Agents

Product Description:

R-Alpine-Borane, also known as (R)-Alpine-Borane or (R)-B-3-pinanyl-9-borabicyclo[3.3.1]nonane, is a chiral organoborane reagent derived from the hydroboration of α-pinene with 9-borabicyclo[3.3.1]nonane (9-BBN). It is a commercially available, air- and moisture-sensitive reagent typically supplied as a solution in tetrahydrofuran (THF). Its primary and most significant application is in asymmetric synthesis, specifically as a chiral reducing agent for the enantioselective reduction of prochiral ketones. It exhibits high enantioselectivity in the reduction of α-acetylenic ketones to yield corresponding propargylic alcohols with the (R)-configuration. This transformation is a cornerstone in the synthesis of chiral building blocks for pharmaceuticals, natural products, and other fine chemicals. The reagent's selectivity arises from its well-defined chiral environment provided by the pinanyl group. While less common than some other chiral reducing agents like CBS catalysts, R-Alpine-Borane remains a valuable and specific tool in the synthetic chemist's repertoire for achieving high enantiomeric excess in targeted reductions. It requires handling under inert atmosphere (argon or nitrogen) due to its pyrophoric nature and sensitivity to protic solvents.

Physical Properties

Boiling Point: >55 °C(lit.)

Flash Point: 157.2 °C

Density: 0.947 g/mL at 25 °C(lit.)

Safety Information

Packing Level:

Hazard Category: 4.2

Transport Codes: 2845