317020

(−)-DIP-Chloride^™

• Synonym(s): (−)-B-Chlorodiisopinocampheylborane, (−)-Ipc₂BCl
• Empirical Formula (Hill Notation): C₂₀H₃₄BCl
• CAS Number: 85116-37-6
• Molecular Weight: 320.75
• Beilstein: 5937756
• MDL number: MFCD00074807
• UNSPSC Code: 12352001
• PubChem Substance ID: 24859060
• NACRES: NA.22

Properties

• form: solid
• Quality Level: 100
• mp: 52-56 °C (lit.)
• SMILES string: C[C@H]1[C@@H](CC2CCC1C2(C)C)B(Cl)[C@@H]3CC4CCC([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

Application

Both (+)- and (-)-DIP-chloride are used for asymmetric reduction of prochiral ketones and for the preparation of β-amino alcohols.

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).

Legal Information

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

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Skin Corr. 1B
• Storage Class Code: 8A - Combustible corrosive hazardous materials
• WGK: WGK 3
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves