chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane

• ChemBase ID: 146654
• Molecular Formular: C20H34BCl
• Molecular Mass: 320.74796
• Monoisotopic Mass: 320.24420917
• SMILES: B([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)Cl
• Canonical SMILES: ClB([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C
• InChI: InChI=1S/C20H34BCl/c1-11-15-7-13(19(15,3)4)9-17(11)21(22)18-10-14-8-16(12(18)2)20(14,5)6/h11-18H,7-10H2,1-6H3/t11-,12-,13+,14+,15-,16-,17-,18-/m0/s1
• InChIKey: PSEHHVRCDVOTID-NAVXHOJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• IUPAC Traditional name: chlorobis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• Synonyms: (+)-Ipc2BCl; (+)-B-Chlorodiisopinocampheylborane; (+)-DIP-Chloride™; (+)-B-氯二异蒎莰硼烷

Database IDs

• CAS Number: 112246-73-8
• PubChem SID: 162240847; 24859059
• PubChem CID: 9923113

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.0043
• LogD (pH = 7.4): 7.0043
• Log P: 7.0043
• Molar Refractivity: 91.5303 cm^3
• Polarizability: 38.477573 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 53-55 °C(lit.)
• Flash Point: 110 °C; 230 °F

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34-37
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2

Product Information

• Purity: 90-105% (approx.)
• Empirical Formula (Hill Notation): C20H34BCl

DETAILS

Sigma Aldrich - 317012

Application
Both (+)- and (-)-DIP-chloride are used for asymmetric reduction of prochiral ketones1,2 and for the preparation of β-amino alcohols.2,3
Excellent reagent for asymmetric reductions.
For a short paper on the preparation of DIP halides and their use in stereoselective reductions see ACS Symp. Ser. 641, 84-97 (1996).
Packaging
5, 25 g in glass bottle
Legal Information
DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC