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Merck
CN

188913

Catecholborane

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

Key Documents

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InChI key

CENMEJUYOOMFFZ-UHFFFAOYSA-N

InChI

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

SMILES string

[bH]1oc2ccccc2o1

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

Quality Level

200

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.

Other Notes

Material may precipitate naturally over time; the precipitate isinert

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

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ7841
SHBQ5440
SHBK9116
SHBH7523
SHBH1447V

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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
European Journal of Organic Chemistry, 4596-4596 (2006)
The Journal of Organic Chemistry, 55, 5190-5190 (1990)

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