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188913

Sigma-Aldrich

Catecholborane

98%

Sinónimos:

Catecholatoborane, Catecholborane (CB), Pyrocatecholborane

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About This Item

Fórmula empírica (notación de Hill):
C6H5BO2
Número de CAS:
274-07-7
Peso molecular:
119.91
Beilstein/REAXYS Number:
972072
EC Number:
205-991-5
MDL number:
MFCD00005846
UNSPSC Code:
12352103
PubChem Substance ID:
24851357
NACRES:
NA.22

assay

98%

form

liquid

reaction suitability

reagent type: reductant

refractive index

n20/D 1.507 (lit.)

bp

50 °C/50 mmHg (lit.)

mp

12 °C (lit.)

density

1.125 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[bH]1oc2ccccc2o1

InChI

1S/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H

InChI key

CENMEJUYOOMFFZ-UHFFFAOYSA-N

Categorías relacionadas

Application

A monofunctional hydroborating agent which reduces β-hydroxyketones to 1,3-diols. Effects conjugate reduction of α,β-enones.
Used to prepare B-alkylcatecholboranes which were used, in turn, to generate alkyl radicals forming aryl ethers from quinones. Employed in a preparation of C2-symmetric boron complexes from methylenebis(oxazolines) used for enantioselective reduction of ketones.

Legal Information

Made under U.S. Pat. No. 6,204,405.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H225,H314

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

35.6 °F - closed cup

flash_point_c

2 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

649309

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Sigma-Aldrich

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The Journal of Organic Chemistry, 55, 5678-5678 (1990)
Eveline Kumli et al.
Organic letters, 8(25), 5861-5864 (2006-12-01)
Addition of alkyl radicals generated from B-alkylcatecholboranes onto 1,4-benzoquinones leads to substituted hydroquinones in good overall yields. Formation of aryl ethers via a unique radical addition to the oxygen atom of the enone system is the main reaction when bulky
The Journal of Organic Chemistry, 55, 5190-5190 (1990)
European Journal of Organic Chemistry, 4596-4596 (2006)

Artículos

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

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