Description

Bis[(+)-pinanediolato]diboron (CAS No. 230299-05-5) is a highly specialized organoboron compound with the molecular formula C₂₀H₃₂B₂O₄. This chiral reagent is widely utilized in asymmetric synthesis and cross-coupling reactions due to its unique pinanediolato ligand framework, which enhances stereoselectivity. The compound is supplied as a high-purity crystalline solid, ensuring optimal performance in catalytic applications. Its stability under inert conditions makes it a reliable choice for advanced organic transformations, including Suzuki-Miyaura couplings and borylation reactions. Ideal for researchers and scientists working in pharmaceutical development, material science, and fine chemical synthesis.

Properties

• CAS Number: 230299-05-5
• Complexity: 612
• IUPAC Name: (1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S,2S,6R,8S)-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-/m0/s1
• InChI Key: VNEZFUGEQURPEN-YAEFTDRSSA-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, 230299-05-5, bis((+)-pinanediolato)diboron, 673-659-0, 2,2′-Bi-4,6-methano-1,3,2-benzodioxaborole, dodecahydro-3a,3’a,5,5,5′,5′-hexamethyl-, (3aS,3’aS,4S,4’S,6S,6’S,7aR,7’aR)-, MFCD27664803, 230299-17-9, (1S,2S,6R,8S)-2,9,9-trimethyl-4-[(1S,2S,6R,8S)-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, (3aS,3’aS,4S,4’S,6S,6’S,7aR,7’aR)-Dodecahydro-3a,3’a,5,5,5′,5′-hexamethyl-2,2′-bi-4,6-methano-1,3,2-benzodioxaborole, SCHEMBL23451168, AKOS027256617, AS-37624, CS-0133037, (3aS,3 inverted exclamation markaaS,4S,4 inverted exclamation markaS,6S,6 inverted exclamation markaS,7aR,7 inverted exclamation markaaR)-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 primarily used as a chiral boronating agent in asymmetric synthesis, enabling the stereoselective formation of C-B bonds. It is particularly valuable in Suzuki-Miyaura cross-coupling reactions for constructing enantiomerically enriched biaryl compounds. The compound also finds application in the preparation of boron-containing intermediates for drug discovery and agrochemical research. Its robust performance in borylation reactions makes it a staple in organometallic chemistry laboratories.

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

• Acute Tox. 4 (25%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• Acute Tox. 4 (25%)
• STOT SE 3 (100%)

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