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.
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
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) |
