CATECHOLBORANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H5BO2
Molecular Weight	119.914
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

B1OC2=C(O1)C=CC=C2

InChI

InChIKey=CENMEJUYOOMFFZ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H5BO2
Molecular Weight	119.914
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Electronic tuning of a carbene center via remote chemical induction, and relevant effects in catalysis.	2010-10-04	20821762
An efficient nickel catalyst for the reduction of carbon dioxide with a borane.	2010-07-07	20540579
Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.	2010-04-16	20334398
Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine.	2010-03-04	20335981
Total synthesis and absolute configuration of the marine norditerpenoid xestenone.	2009-11-24	20098605
Highly enantioselective oxazaborolidine-catalyzed reduction of 1,3-dicarbonyl compounds: role of the additive diethylaniline.	2009-04-02	19278241
Activation of B-H bonds by an oxo-rhenium complex.	2008-12-21	19153615
C-H bond activation of heteroarenes mediated by a half-sandwich iron complex of N-heterocyclic carbene.	2008-12-17	19007215
Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands.	2008-10-06	18774796
Oxygen-directed intramolecular hydroboration.	2008-07-23	18572941
Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series.	2008-01-01	17981469
Structural elucidation of a nickel boryl complex. A recyclable borylation Ni(II) reagent of bromobenzene.	2007-11-21	17971965
Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.	2006-07-17	16708414
TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.	2006-07-06	16805561
Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes.	2006-05-11	16671758
Fully stereocontrolled total syntheses of the prostacyclin analogues 16S-iloprost and 16S-3-oxa-iloprost by a common route, using alkenylcopper-azoalkene conjugate addition, asymmetric olefination, and allylic alkylation.	2005-12-21	16351123
Photoswitching of the Lewis acidity of a catecholborane bearing an azo group based on the change in coordination number of boron.	2005-09-01	16119929
A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction.	2005-01	15635240
Six- and eightfold palladium-catalyzed cross-coupling reactions of hexa- and octabromoarenes.	2004-12-17	15551314
In quest of factors that control the enantioselective catalytic Markovnikov hydroboration/oxidation of vinylarenes.	2004-12-03	15540267
Eremophilane sesquiterpenes from capsidiol.	2004-10-29	15497966
Transition-metal-mediated synthesis of novel carbocyclic nucleoside analogues with antitumoral activity.	2004-10-11	15372578
Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane.	2004-08-04	15281807
Formation of inclusion organoactinide complexes with boron-containing macrocycles.	2004-04-28	15099079
On the origin of regio- and stereoselectivity in the rhodium-catalyzed vinylarenes hydroboration reaction.	2004-04-16	15074912
Structure investigation of TiIV-BODOLates involved in the catalytic asymmetric reduction of ketones using catecholborane.	2004-01-05	14695563
Effective modular iminooxazoline (IMOX) ligands for asymmetric catalysis: [Zn(IMOX)]-promoted enantioselective reduction of ketones by catecholborane.	2003-10-20	14579441
Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols.	2003-09-17	16220949
Substrate-controlled highly diastereoselective synthesis of primary and secondary diorganozinc reagents by hydroboration/boron-zinc exchange sequence.	2003-06-16	12866543
Addition reactions at the 16(17) double bond of 3-methoxy-13alpha-estra-1,3,5(10),16-tetraene.	2003-03	12628692
Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers.	2003-01-10	12515454
Asymmetric synthesis of a selective endothelin A receptor antagonist.	2002-08	12192138
Asymmetric synthesis of syn- and anti-1,3-amino alcohols.	2002-06-12	12047156
An unprecedented recyclable catalyst system for asymmetric hydroboration.	2001-09-21	12240325
Asymmetric reduction of ketones with catecholborane using 2,6-BODOL complexes of titanium(IV) as catalysts.	2001-05-18	11411988

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:13:22 GMT 2025` Edited by `admin` on `Mon Mar 31 21:13:22 GMT 2025`
Record UNII	UB69382H5J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CATECHOLBORANE

Common Name

English

BENZCATECHINBORANE

Preferred Name

English

1,3,2-BENZODIOXABOROLE

Systematic Name

English

PYROCATECHOLBORANE

Common Name

English

CATECHOLBORANE [MI]

Common Name

English

1,3,2-BENZODIOXABOROLANE

Systematic Name

English

CATECHOLATOBORANE

Common Name

English

Code System Code Type Description

MERCK INDEX

m3173