648418

(−)-DIP-Chloride^™ solution

50-65 wt. % in heptane

• Synonym(s): (−)-B-Chlorodiisopinocampheylborane, (−)-Chlorodiisopinocampheylborane, Chlorobis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane, Diisopinocampheylchloroborane
• Empirical Formula (Hill Notation): C₂₀H₃₄BCl
• CAS Number: 85116-37-6
• Molecular Weight: 320.75
• MDL number: MFCD00074807
• UNSPSC Code: 12352001
• PubChem Substance ID: 24883579
• NACRES: NA.22

Properties

• Quality Level: 100
• concentration: 50-65 wt. % in heptane
• density: 0.895 g/mL at 25 °C
• SMILES string: C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B(Cl)[C@@H]3C[C@@H]4C[C@H]([C@H]3C)C4(C)C
• 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
• InChI key: PSEHHVRCDVOTID-VMAIWCPRSA-N

Description

General description

(−)-DIP-Chloride^™ solution is a pinane-based asymmetric reducing agent that is commonly used in asymmetric reduction reactions.

Application

(−)-Diisopinocampheylchloroborane [(−)-DIP-Chloride^™] solution can be used as a reducing reagent for the:

• Enantioselective reduction of α, β-unsaturated trifluoromethyl ketones into corresponding secondary allylic alcohols.
• Asymmetric reduction of aromatic and aliphatic α-halomethyl ketones to haloalcohols.

It can also be used as a catalyst for the enantioselective asymmetric Pictet-Spengler reaction.

Legal Information

DIP-Chloride is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07,GHS09
• signalword: Danger
• hcodes: H225,H304,H314,H336,H410
• pcodes: P210 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: <-22.0 °F - closed cup
• flash_point_c: < -30 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter