Catecholborane

Product Information

Molecular Formula:
C6H4BO2
Molecular Weight:
119.91
Description
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.
Synonyms
Catecholborane;1,3,2-Benzodioxaborole;274-07-7;Benzo[d][1,3,2]dioxaborole;1,3,2$l^{2}-benzodioxaborole;CENMEJUYOOMFFZ-UHFFFAOYSA-N
Canonical SMILES
[B]1OC2=CC=CC=C2O1
InChI
InChI=1S/C6H4BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4H
InChI Key
ZDQWVKDDJDIVAL-UHFFFAOYSA-N
Boiling Point
121.385°C at 760 mmHg
Melting Point
12°C(lit.)
Flash Point
35.6 °F - closed cup
Purity
95%
Density
1.125
Appearance
clear colorless solution
Storage
2-8°C
Refractive Index
n20/D 1.507 (lit.)

Safety Information

Hazards
H225 - H314
Precautionary Statement
P210 - P280 - P305 + P351 + P338 - P310

Computed Properties

Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
119.0304345 g/mol
Monoisotopic Mass
119.0304345 g/mol
Topological Polar Surface Area
18.5Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
95.2
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

Publication Number Title Priority Date
JP-2022037094-A Method for producing a polyene compound having a hydroxyl group 2021-12-14
CN-113969414-A Tellurium-modified nickel telluride/nickel selenide heterojunction hydrogen evolution catalyst and preparation method and application thereof 2021-11-26
CN-114105822-A Pseudo C2Symmetrical chiral diallyl substituted compound and preparation method and application thereof 2021-11-16
CN-113880873-A Hydroboration reaction method for catalyzing olefin by calcium halide 2021-10-25
CN-113880799-A Intermediate compound for preparing paclitaxel, synthesis method thereof and synthesis method of paclitaxel 2021-08-06
CN-113584518-A Tellurium/nickel telluride hydrogen evolution catalyst and preparation method and application thereof 2021-07-02
CN-113652707-A Nickel telluride hydrogen evolution catalyst and preparation method and application thereof 2021-07-02
CN-112794860-A Oxazole pyrimidone amide compound or medicinal salt thereof, preparation method and application 2021-03-24
CN-112794860-B Oxazole pyrimidone amide compound or medicinal salt thereof, preparation method and application 2021-03-24
CN-112624981-A Preparation method of 2-fluoro-5- [ (4-oxo-3H-2, 3-diazanaphthyl) methyl ] benzoic acid 2021-03-09

Literatures

PMID Publication Date Title Journal
22213362 2012-01-27 Catalytic non-conventional trans-hydroboration: a theoretical and experimental perspective Chemistry (Weinheim an der Bergstrasse, Germany)
22180016 2012-01-16 Silylboranes as new sources of silyl radicals for chain-transfer reactions Chemistry (Weinheim an der Bergstrasse, Germany)
22057739 2011-12-23 Transition-metal-catalyzed synthesis of diboranes(4) Angewandte Chemie (International ed. in English)
21819141 2011-09-07 A radical procedure for the anti-Markovnikov hydroazidation of alkenes Journal of the American Chemical Society
21819075 2011-09-05 Net heterolytic cleavage of B-H and B-B bonds across the N-Pd bond in a cationic (PNP)Pd fragment Inorganic chemistry
21413735 2011-04-18 How does the nickel pincer complex catalyze the conversion of CO2 to a methanol derivative? A computational mechanistic study Inorganic chemistry
20821762 2010-10-04 Electronic tuning of a carbene center via remote chemical induction, and relevant effects in catalysis Chemistry (Weinheim an der Bergstrasse, Germany)
20540579 2010-07-07 An efficient nickel catalyst for the reduction of carbon dioxide with a borane Journal of the American Chemical Society
20334398 2010-04-16 Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts Organic letters
20335981 2010-03-04 Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine Molecules (Basel, Switzerland)
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Related Products

Online Inquiry
  • Verification code
USA
  • International:
  • US & Canada (Toll free):
  • Email:
  • Fax:
UK
  • Email:
Copyright © 2024 BOC Sciences. All rights reserved.
Top
Inquiry Basket