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Catecholborane, 50% w/w in toluene (98% dry wt.)

Product Code. 15447755
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Product Code. 15447755 Supplier Thermo Scientific Alfa Aesar Supplier No. H30234.22
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Description

CAS: 274-07-7 | C6H4BO2 | 118.906 g/mol

Employed in organic synthesis. Addition of catecholborane to vinylarenes in the presence of Wilkinson's catalyst, gives Markovnikov hydroboration products exclusively, whereas the corresponding reaction with a-substituted vinylarenesgivesgood yields of vinylboronate. Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation. Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Employed in organic synthesis. Addition of catecholborane to vinylarenes in the presence of Wilkinson′s catalyst, gives Markovnikov hydroboration products exclusively, whereas the corresponding reaction with a-substituted vinylarenesgivesgood yields of vinylboronate. Hydroboration with catecholborane, followed by treatment with easily available reagents such as alkenyl sulfones or alkynyl phenyl sulfones in the presence of a radical initiator, represents an effective and simple one-pot procedure for direct vinylation, formylation, and cyanation. Catecholborane may be used as a stereoselective reducing agent when converting β-hydroxy ketones to syn 1,3-diols.

Solubility
Reacts with water.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from water, moisture.
TRUSTED_SUSTAINABILITY

Chemical Identifiers

CAS 274-07-7
Molecular Formula C6H4BO2
Molecular Weight (g/mol) 118.906
MDL Number MFCD00005846
InChI Key ZDQWVKDDJDIVAL-UHFFFAOYSA-N
Synonym catecholborane, 1,3,2-benzodioxaborole, benzo d 1,3,2 dioxaborole, 1,3,2$l^ 2-benzodioxaborole, cenmejuyoomffz-uhfffaoysa-n, catechol borane, catecholatoborane, benzcatechinborane, pyrocatecholborane
PubChem CID 6327445
IUPAC Name 1,3,2$l^{2}-benzodioxaborole
SMILES [B]1OC2=CC=CC=C2O1

Specifications

Density 0.911
Refractive Index 1.5025
Quantity 100 g
UN Number UN2924
Sensitivity Moisture sensitive
Solubility Information Reacts with water.
Formula Weight 119.92
Percent Purity 98%
Concentration or Composition (by Analyte or Components) 50% w/w in toluene
Assay (dry wt.)
Chemical Name or Material Catecholborane
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