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TCI

CAS 2763205-15-6

2',7'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] TCI B6552

2',7'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] TCI B6552

Chemical Identity

Other names
2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[fluorene-9,5'-pyrido[3',2':4,5]cyclopenta[1,2-b]pyridine] · SpiroBpy-Bpin
CAS No.
2763205-15-6
PubChem
CID 168438051
Formula
C35H36B2N2O4
Molecular weight
570.30 g/mol
Purity
>95.0%(HPLC)(qNMR)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
2',7'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3,13-diazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene-8,9'-fluorene]
SMILES
B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)C4=C(C35C6=C(C7=C5C=CC=N7)N=CC=C6)C=C(C=C4)B8OC(C(O8)(C)C)(C)C
InChIKey
HUQKDLAJTKYRCC-UHFFFAOYSA-N
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TCI B6552 is a spiro-linked building block bearing two pinacol boronate groups at the 2' and 7' positions of a spiro[cyclopenta-dipyridine-fluorene] framework. Its difunctional boronate handles make it a convenient monomer for palladium-catalysed Suzuki–Miyaura cross-coupling and for the assembly of conjugated oligomers and polymers. The rigid, orthogonal spiro geometry combined with electron-poor pyridine nitrogens is of particular interest in organic optoelectronic material research and in nitrogen-donor ligand design. AMI Scientific supplies this TCI product in 100 mg and 500 mg pack sizes; always consult the official TCI documentation and safety data sheet before use.

Advantages (TCI brochure)

  • Allows the highly selective introduction of a boryl group at the meta-position of benzene ring
  • Applicable to meta-selective borylation of arene moieties in a wide range of substrates

From the TCI brochure

  • Meta-selective C-H borylation of arene moieties in a wide range of substrates

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References cited in the TCI brochure

  1. Boobalan Ramadoss. Remote steric control for undirected meta -selective C–H activation of arenes Science, 2022. doi:10.1126/science.abm7599
  2. Matteo Zanda. SYNFORM ISSUE 2022/06 Synlett, 2022. doi:10.1055/s-0041-1737487