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232734

Sigma-Aldrich

R-Alpine-Borane® solution

0.5 M in THF

Synonym(s):

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

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100 ML
MXP 4,021.00

MXP 4,021.00

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100 ML
MXP 4,021.00

About This Item

Empirical Formula (Hill Notation):
C18H31B
CAS Number:
73624-47-2
Molecular Weight:
258.25
MDL number:
MFCD00074776
UNSPSC Code:
12352005
PubChem Substance ID:
24853817
NACRES:
NA.22

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form

liquid

optical activity

[α]20/D −3.0°, neat

concentration

0.5 M in THF

density

0.896 g/mL at 25 °C

SMILES string

C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B3[C@@H]4CCC[C@H]3CCC4

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

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General description

R-Alpine-Borane® is a chiral reducing agent, synthesized from (+)-α-pinene via hydroboration.[1][2]

Application

R- and S-Alpine-Boranes are used for asymmetric reduction of aldehydes[3][4] and prochiral ketones.[5][6][4]
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.[7]
  • (R)-1-(p-Tolyl)-1-pentyn-3-ol, an intermediate for the enatioselective synthesis of (R)-incrustoporin.[8]
  • N-(tert-Butyloxycarbonyl)-(4S)-[4-2H]-1-L-homoserine tert-butyl ester, an intermediate for synthesizing (4S)-[4-2H]-L-homoserine.[9]

Legal Information

Alpine-Borane is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F

Flash Point(C)

-17 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK1156
SHBH1202V
SHBD6994V
SHBB3995
57396MM

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Biosynthesis of 4-Methylproline in Cyanobacteria: Cloning of n osE and n osF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities.
Luesch H, et al.
The Journal of Organic Chemistry, 68(1), 83-91 (2003)
First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (-)-stagonolide D.
Kumar AS, et al.
Tetrahedron Letters (2016)
Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola.
Rossi R, et al.
Tetrahedron Asymmetry, 10(6), 1163-1172 (1999)
Tetrahedron Asymmetry, 5, 1061-1061 (1994)
Diisopinocampheylchloroborane, a remarkably efficient chiral reducing agent for aromatic prochiral ketones.
Chandrasekharan J, et al.
The Journal of Organic Chemistry, 50(25), 5446-5448 (1985)
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