bis([(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane); [2-(dimethylamino)ethyl]dimethylamine

• ChemBase ID: 150664
• Molecular Formular: C26H54B2N2
• Molecular Mass: 416.34236
• Monoisotopic Mass: 416.44731054
• SMILES: B[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C.B[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C.CN(C)CCN(C)C
• Canonical SMILES: B[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C.B[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C.CN(CCN(C)C)C
• InChI: InChI=1S/2C10H19B.C6H16N2/c2*1-6-8-4-7(5-9(6)11)10(8,2)3;1-7(2)5-6-8(3)4/h2*6-9H,4-5,11H2,1-3H3;5-6H2,1-4H3/t2*6-,7+,8-,9-;/m00./s1
• InChIKey: QNDCJVKDHWRHGS-NCHGFZPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis([(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane); [2-(dimethylamino)ethyl]dimethylamine
• IUPAC Traditional name: bis([(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane); temed
• Synonyms: (R)-Alpine-Boramine™; (-)-N,N′-Bis(monoisopinocampheylborane)-N,N,N′,N′-tetramethylethylenediamine; (-)-Isopinocampheylborane TMEDA complex; (-)-N,N′-双(单异松蒎基硼烷)-N,N,N′,N′-四甲基乙二胺; (-)-异松蒎基硼烷-四甲基乙二胺络合物

Database IDs

• CAS Number: 67826-92-0
• MDL Number: MFCD00077801
• PubChem SID: 162244825; 24855135
• PubChem CID: 16211704

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.2052
• LogD (pH = 7.4): 3.2052
• Log P: 3.2052
• Molar Refractivity: 44.22 cm^3
• Polarizability: 19.750172 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 139-141 °C(lit.)

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2813
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: 3
• Risk Statements: 15-36/38
• Safety Statements: 26-36-43
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H261-H315-H319
• GHS Precautionary statements: P231 + P232-P305 + P351 + P338-P422
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, 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 2813 4.3/PG 3

Product Information

• Empirical Formula (Hill Notation): C13H27BN

DETAILS

Sigma Aldrich - 251496

Packaging
5 g in glass bottle
Application
Chiral hydroboration reagent.1,2This amine-borane complex has been used as a polarity-reversal catalyst for the kinetic resolution of racemic esters and ketones.3
Legal Information
Alpine-Boramine is a trademark of Sigma-Aldrich Co. LLC