methyl[(1S,2S)-1-phenyl-1-{[(1S,5s,10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-yl]amine

• ChemBase ID: 140663
• Molecular Formular: C22H38BNOSi
• Molecular Mass: 371.43972
• Monoisotopic Mass: 371.28157177
• SMILES: B1([C@H]([C@H]2CCC[C@@H]1CCC2)[Si](C)(C)C)O[C@H]([C@@H](NC)C)c1ccccc1
• Canonical SMILES: CN[C@H]([C@H](c1ccccc1)OB1[C@@H]2CCC[C@H]([C@@H]1[Si](C)(C)C)CCC2)C
• InChI: InChI=1S/C22H38BNOSi/c1-17(24-2)21(18-11-7-6-8-12-18)25-23-20-15-9-13-19(14-10-16-20)22(23)26(3,4)5/h6-8,11-12,17,19-22,24H,9-10,13-16H2,1-5H3/t17-,19-,20+,21+,22-/m0/s1
• InChIKey: ZOZYQBFBLCMBTA-RXZUFOQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl[(1S,2S)-1-phenyl-1-{[(1S,5s,10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-yl]amine
• IUPAC Traditional name: methyl[(1S,2S)-1-phenyl-1-{[(1S,5s,10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]decan-9-yl]oxy}propan-2-yl]amine
• Synonyms: N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine; (+)-9-(1S, 2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane; N,α-二甲基-β-[[(10R)-10-(三甲基硅基)-9-硼杂双环[3.3.2]癸-9-基]氧]-(αS,βS)-苯乙胺; (+)-9-(1S, 2S-伪麻黄碱基)-(10R)-(三甲基硅基)-9-硼杂双环[3.3.2]癸烷

Database IDs

• CAS Number: 848618-13-3
• MDL Number: MFCD09265094
• PubChem SID: 24885323; 162234904
• PubChem CID: 16218304

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.873867
• LogD (pH = 7.4): 5.3188624
• Log P: 7.2965
• Molar Refractivity: 103.1751 cm^3
• Polarizability: 45.530586 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 130-134 °C
• Optical Rotation: [α]22/D +60°, c = 4.5 in chloroform-d

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C22H38BNOSi

DETAILS

Sigma Aldrich - 676675

Application
Air-stable, crystalline pseudoephedrine borinic acid complex which when treated with an appropriate Grignard reagent provides access to homoallylic or homopropargylic alcohols and α-allenyl carbinols.1,2,3
Soderquist Reagents: For allylboration, allenylboration, propargylboration
Packaging
1, 5 g in glass bottle