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

• ChemBase ID: 156183
• 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-;/m11./s1
• InChIKey: QNDCJVKDHWRHGS-AUDPXGPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis([(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane); [2-(dimethylamino)ethyl]dimethylamine
• IUPAC Traditional name: bis([(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane); temed
• Synonyms: (+)-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: 68297-74-5
• MDL Number: MFCD00013212
• PubChem SID: 162250321
• PubChem CID: 12482036

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.)
• Optical Rotation: [α]20/D +69±2°, c = 9% in THF

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Grade: purum
• Empirical Formula (Hill Notation): C26H54B2N2

DETAILS

Sigma Aldrich - 59234

Other Notes
Chiral hydroborating agent; trans-di and trisubstituted olefins give alcohols of high enantiomeric purity upon hydroboration-oxidation. An incorrect sign of optical rotation was reported in the original publication1,2,3; Preparation of amines from olefins3
Preparation Note
produced from (-)-α-pinene