Description

Bis[(-)-pinanediolato]diboron (CAS No. 230299-17-9) is a highly specialized chiral boron reagent widely used in asymmetric synthesis and cross-coupling reactions. With the molecular formula C₂₀H₃₂B₂O₄, this compound features a unique pinanediolato ligand framework, providing exceptional stereoselectivity in organic transformations. It is particularly valuable in Suzuki-Miyaura couplings, enabling the formation of C-C bonds with high enantiomeric purity. Supplied as a white to off-white crystalline solid, this reagent is rigorously tested for purity and stability, ensuring reliable performance in demanding research and industrial applications. Store under inert conditions to maintain reactivity and shelf life.

Properties

• CAS Number: 230299-17-9
• Complexity: 612
• IUPAC Name: (1R,2R,6S,8R)-2,9,9-trimethyl-4-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• InChI: InChI=1S/C20H32B2O4/c1-17(2)11-7-13(17)19(5)15(9-11)23-21(25-19)22-24-16-10-12-8-14(18(12,3)4)20(16,6)26-22/h11-16H,7-10H2,1-6H3/t11-,12-,13-,14-,15+,16+,19-,20-/m1/s1
• InChI Key: VNEZFUGEQURPEN-COLRIBGKSA-N
• Exact Mass: 358.2486698
• Molecular Formula: C20H32B2O4
• Molecular Weight: 358.1
• SMILES: B1(O[C@H]2C[C@H]3C[C@@H]([C@]2(O1)C)C3(C)C)B4O[C@H]5C[C@H]6C[C@@H]([C@]5(O4)C)C6(C)C
• Topological: 36.9
• Monoisotopic Mass: 358.2486698
• Synonyms: bis[(-)-pinanediolato]diboron, 230299-17-9, MFCD02683578, (3aR,3’aR,4R,4’R,6R,6’R,7aS,7’aS)-Dodecahydro-3a,3’a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole, bis((-)-pinanediolato)diboron, AKOS016028422, CS-0145780, O11697, (1R,2R,6S,8R)-2,9,9-trimethyl-4-[(1R,2R,6S,8R)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane, (3aR,3 inverted exclamation markaaR,4R,4 inverted exclamation markaR,6R,6 inverted exclamation markaR,7aS,7 inverted exclamation markaaS)-Dodecahydro-3a,3 inverted exclamation markaa,5,5,5 inverted exclamation marka,5 inverted exclamation marka-hexamethyl-2,2 inverted exclamation marka-bi-4,6-methano-1,3,2-benzodioxaborole

Bis[(-)-pinanediolato]diboron is extensively employed in asymmetric borylation reactions, facilitating the synthesis of chiral boronic esters. It serves as a key intermediate in pharmaceutical research for constructing enantiomerically enriched compounds. The reagent is also utilized in materials science for designing optically active polymers. Its robust stability under mild conditions makes it ideal for catalytic cycles and multistep syntheses.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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