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237701

Sigma-Aldrich

S-Alpine-Borane® solution

0.5 M in THF

Synonym(s):

B-isopinocampheyl-9-borabicyclo[3.3.1]nonane

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About This Item

Empirical Formula (Hill Notation):
C18H31B
CAS Number:
42371-63-1
Molecular Weight:
258.25
MDL number:
MFCD00082390
UNSPSC Code:
12352000
PubChem Substance ID:
24854265
NACRES:
NA.22

form

liquid

optical activity

[α]22/D +1.2°, neat

concentration

0.5 M in THF

density

0.897 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-/m0/s1

InChI key

VCDGSBJCRYTLNU-NEXGVSGLSA-N

General description

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

Application

R- and S-Alpine-Boranes are used for asymmetric reduction of aldehydes[2][3] and prochiral ketones.[4][5][3]
S-Alpine-Borane® solution may be used to prepare:
  • 5(S)-methyl 5-hydroxy-8-(tetrahydropyran-2-yloxy)-6-octynoate, an intermediate for the stereocontrolled total synthesis of leukotriene B4.[6]
  • (+)-(S)-4-hydroxy-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate[7]
  • (R)-1-(tert-Butyldiphenylsilyloxy)pent-3-yn-2-ol, an intermediate for the preparation of (S)-4,5-dihydroxypentane-2,3-dione (DPD).[8]

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 - Pyr. Liq. 1 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

237701-VAR:
237701-100ML:4548173122427
237701-BULK:
237701-800ML:4548173122434

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL2715
SHBF3460V
SHBB0239
16103MH
06503CW

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An efficient synthesis of the precursor of AI-2, the signalling molecule for inter-species quorum sensing.
Ascenso OS, et al.
Bioorganic & Medicinal Chemistry, 19(3), 1236-1241 (2011)
(-)-Sparteine-Mediated Stereoselective Intramolecular Carbolithiation of 4-Substituted 5-Hexynyl Carbamates. Synthesis of Enantiopure 1, 3-Difunctionalized Alkylidene Cyclopentanes.
Oestreich M, et al.
The Journal of Organic Chemistry, 64(23), 8616-8626 (1999)
Synlett, 561-561 (1993)
Tetrahedron Asymmetry, 5, 1061-1061 (1994)
Total synthesis of leukotriene B4.
Kerdesky FAJ, et al.
The Journal of Organic Chemistry, 58(13), 3516-3520 (1993)
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