237701

S-Alpine-Borane^® solution

0.5 M in THF

• Sinónimos: B-isopinocampheyl-9-borabicyclo[3.3.1]nonane
• Fórmula empírica (notación de Hill): C₁₈H₃₁B
• Número de CAS: 42371-63-1
• Peso molecular: 258.25
• MDL number: MFCD00082390
• UNSPSC Code: 12352000
• PubChem Substance ID: 24854265
• NACRES: NA.22

Propiedades

• 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

Descripción

General description

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

Application

R- and S-Alpine-Boranes are used for asymmetric reduction of aldehydes and prochiral ketones.

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.
• (+)-(S)-4-hydroxy-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• (R)-1-(tert-Butyldiphenylsilyloxy)pent-3-yn-2-ol, an intermediate for the preparation of (S)-4,5-dihydroxypentane-2,3-dione (DPD).

Legal Information

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

Información de seguridad

• pictograms: GHS02,GHS08,GHS07
• signalword: Danger
• hcodes: H225,H250,H302,H319,H335,H351
• pcodes: P210 - P231 - P280 - P302 + P334 - P370 + P378 - P422
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Pyr. Liq. 1 - STOT SE 3
• target_organs: Respiratory system
• supp_hazards: EUH019
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter