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188913

Catecholborane

Name: Catecholborane
Brand: ALDRICH

98%

Synonym(s):

Catecholatoborane, Catecholborane (CB), Pyrocatecholborane

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About This Item

Empirical Formula (Hill Notation):

C₆H₅BO₂

CAS Number:

274-07-7

Molecular Weight:

119.91

UNSPSC Code:

12352103

NACRES:

NA.22

PubChem Substance ID:

24851357

EC Number:

205-991-5

Beilstein/REAXYS Number:

972072

MDL number:

MFCD00005846

Assay:

98%

Form:

liquid

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Properties

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

Description

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.

Other Notes

Material may precipitate naturally over time; the precipitate isinert

Legal Information

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

pictograms

GHS02,GHS05

signalword

Danger

hcodes

H225,H314

pcodes

P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

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Articles

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.

Radical addition to 1,4-benzoquinones: addition at O- versus C-atom.

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)

View All Related Papers

Global Trade Item Number

SKU	GTIN
188913-25G-A	04061838758989
188913-100G-A	04061838134936