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709905

Sigma-Aldrich

Fluorene-2-boronic acid

Synonym(s):

9H-Fluoren-2-yl-boronic acid

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About This Item

Linear Formula:
C13H9B(OH)2
CAS Number:
480424-61-1
Molecular Weight:
210.04
MDL number:
MFCD05664106
UNSPSC Code:
12352103
PubChem Substance ID:
329762520
NACRES:
NA.22

form

solid

mp

125-129 °C

SMILES string

OB(O)c1ccc-2c(Cc3ccccc-23)c1

InChI

1S/C13H11BO2/c15-14(16)11-5-6-13-10(8-11)7-9-3-1-2-4-12(9)13/h1-6,8,15-16H,7H2

InChI key

OHGJAUSHXQCSQX-UHFFFAOYSA-N

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General description

May contain varying amounts of anhydride

Application

Fluorene-2-boronic acid can be used as a substrate in:
  • Copper-catalyzed γ-arylation of carboxamides.
  • Au(I)-catalyzed protodeboronation reactions.
  • Pd-catalyzed C-H monofunctionalization of benzoquinone.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eric M Woerly et al.
Journal of the American Chemical Society, 132(20), 6941-6943 (2010-05-06)
Stimulated by the substantial challenge of synthesizing the complex and sensitive stereogenic allene-containing core of (-)-peridinin, the first stereocontrolled coupling of haloallenes with boronic acids has been achieved. This new method and the principles that emerged during its development stand
Gold-Catalyzed Proto-and Deuterodeboronation
Barker G, et al.
The Journal of Organic Chemistry, 80(20), 9807-9816 (2015)
Palladium-Catalyzed Direct C-H Functionalization of Benzoquinone
Walker SE, et al.
Angewandte Chemie (International Edition in English), 126(50), 14096-14099 (2014)
Copper-Catalyzed Arylation of Remote C (sp3)- H Bonds in Carboxamides and Sulfonamides
Li Z, et al.
Angewandte Chemie (International Edition in English), 57(40), 13288-13292 (2018)

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