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

• ChemBase ID: 139987
• 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-/m1/s1
• InChIKey: PSEHHVRCDVOTID-VMAIWCPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chlorobis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• IUPAC Traditional name: chlorobis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
• Synonyms: (-)-DIP-Chloride™ solution; (-)-Ipc2BCl; (-)-B-Chlorodiisopinocampheylborane; (-)-DIP-Chloride™; (-)-DIP-Chloride™ 溶液; (-)-B-二异松蒎基氯硼烷

Database IDs

• CAS Number: 85116-37-6
• MDL Number: MFCD00074807
• Beilstein Number: 5937756
• PubChem SID: 24883579; 24859060; 162234232; 24884095; 24883580
• PubChem CID: 11131038

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: 52-56 °C(lit.)
• Flash Point: <-22 °F; <-30 °C; 110 °C; 230 °F; 27 °C; 80.6 °F
• Density: 0.895 g/mL at 25 °C; 0.929 g/mL at 25 °C; 0.954 g/mL at 25 °C

Safety Information

• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N)
• UN Number: 2920; 2924; 3261
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2
• Risk Statements: 10-34-37; 11-34-48/20-51/53-62-65-67; 11-34-50/53-65-67; 34
• Safety Statements: 16-26-36/37/39-45-61-62; 26-36/37/39-45
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H314-H336-H361-H373-H411; H225-H304-H314-H336-H410; H226-H314-H335; H314
• GHS Precautionary statements: P210-P261-P273-P280-P301 + P310-P305 + P351 + P338; P261-P280-P305 + P351 + P338-P310; 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; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2; UN 2924 3/PG 2; UN 3261 8/PG 2

Product Information

• Concentration: 50-65 wt. % in heptane; 50-65 wt. % in hexanes; 65-75 wt. % in α-pinene
• Empirical Formula (Hill Notation): C20H34BCl

DETAILS

Sigma Aldrich - 655295

Packaging
25, 100 mL in glass bottle
Legal Information
DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 648418

Packaging
25, 100 mL in glass bottle
Legal Information
DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 648426

Packaging
25, 100 mL in glass bottle
Legal Information
DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 317020

Application
Both (+)- and (-)-DIP-chloride are used for asymmetric reduction of prochiral ketones1,2 and for the preparation of β-amino alcohols.2,3
Reagent used for an enantioselective reduction of (chloroacetyl) benzofurans to chlorohydrins which serve as intermediates for the corresponding epoxides and aminoalcohols. For a short paper on the preparation of DIP halides and their use in stereoselective reductions see Chem. Commun. 1053 (1994).
Packaging
5, 25, 100 g in glass bottle
Legal Information
DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC