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R-Alpine-Borane® solution

ALDRICH/232734 - 0.5 M in THF

Synonym: B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane solution

CAS Number: 73624-47-2
Empirical Formula (Hill Notation): C18H31B
Molecular Weight: 258.25
MDL Number: MFCD00074776
Linear Formula: C18H31B
Product Type: Chemical

Catalog Number PKG Qty. Price Quantity
45-232734-100ML 100 mL
$197.00
1/EA
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concentration 0.5 M in THF
density 0.896 g/mL at 25 °C
form liquid
InChI 1S/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13+,14-,15+,16-,17-/m1/s1
InChI key VCDGSBJCRYTLNU-PHPOFCCKSA-N
optical activity [α]20/D −3.0°, neat
Quality Level 100 
SMILES string C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B3[C@@H]4CCC[C@H]3CCC4
Application: R- and S-Alpine-Boranes are used for asymmetric reduction of aldehydes and prochiral ketones.
Application: R-Alpine-Borane® solution may be used to prepare:
• (R)-5-(Benzyloxy)pent-3-y-2-ol, an intermediate for the stereoselective total synthesis of (-)-stagonolide D.
• (R)-1-(p-Tolyl)-1-pentyn-3-ol, an intermediate for the enatioselective synthesis of (R)-incrustoporin.
• N-(tert-Butyloxycarbonyl)-(4S)-[4-2H]-1-L-homoserine tert-butyl ester, an intermediate for synthesizing (4S)-[4-2H]-L-homoserine.
General description: R-Alpine-Borane® is a chiral reducing agent, synthesized from (+)-α-pinene via hydroboration.
Legal Information: Alpine-Borane is a registered trademark of Merck KGaA, Darmstadt, Germany
Packaging: 100 mL in Sure/Seal™
Density 0.896 g/mL at 25 °C
UNSPSC 12352005

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