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

• ChemBase ID: 140744
• Molecular Formular: C23H39B
• Molecular Mass: 326.36676
• Monoisotopic Mass: 326.31448165
• SMILES: B(CC=C)([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
• Canonical SMILES: C=CCB([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/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m1/s1
• InChIKey: ZIXZBDJFGUIKJS-RLEROFIGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-en-1-ylbis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• IUPAC Traditional name: prop-2-en-1-ylbis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• Synonyms: (-)-B-Allyldiisopinocampheylborane solution; (-)-Ipc2B(allyl)borane solution; (-)-B-二异松莰烯基烯丙基硼; (-)-Ipc2B(烯丙基)硼烷

Database IDs

• CAS Number: 85116-38-7
• PubChem SID: 162234984; 24885432
• PubChem CID: 11110195

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 7.4905
• LogD (pH = 7.4): 7.4905
• Log P: 7.4905
• Molar Refractivity: 100.001 cm^3
• Polarizability: 42.03943 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Boiling Point: 35-36 °C
• Flash Point: -49 °C; -56.2 °F
• Density: 0.638 g/mL at 25 °C
• Optical Rotation: [α]20/D -35 to ±5°, c = 1

Safety Information

• European Hazard Symbols: Flammable (F); Nature polluting (N); Harmful (Xn)
• UN Number: 1265
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36/37/38-51/53-65-67
• Safety Statements: 16-26-61-62
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H304-H315-H319-H335 + H336-H411
• GHS Precautionary statements: P210-P261-P273-P301 + P310-P305 + P351 + P338-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1265 3/PG 2
• Storage Temperature: -20°C

Product Information

• Concentration: 1 M in pentane
• Linear Formula: (C10H17)2BCH2CH=CH2

DETAILS

Sigma Aldrich - 678538

Application
Convenient, salt-free, stable solution of a chiral allyl borane for asymmetric allylation of aldehydes leading to chiral homoallylic alcohols.1,2
General description
Material may become hazy upon cooler storage, this will not affect use
Packaging
5, 25 mL in ampule