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188913

Sigma-Aldrich

Catecholborane

98%

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Synonym(s):
Catecholatoborane, Catecholborane (CB), Pyrocatecholborane
Empirical Formula (Hill Notation):
C6H5BO2
CAS Number:
274-07-7
Molecular Weight:
119.91
Beilstein:
972072
EC Number:
205-991-5
MDL number:
MFCD00005846
UNSPSC Code:
12352103
PubChem Substance ID:
24851357
NACRES:
NA.22

Quality Level

200

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

Related Categories

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

Signal Word

Danger

Hazard Statements

H225,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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, 5678-5678 (1990)
The Journal of Organic Chemistry, 55, 5190-5190 (1990)

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