U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CATECHOLBORANE

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

PubMed

TitleDatePubMed
Asymmetric reduction of ketones with catecholborane using 2,6-BODOL complexes of titanium(IV) as catalysts.
2001 May 18
An unprecedented recyclable catalyst system for asymmetric hydroboration.
2001 Sep 21
Asymmetric synthesis of a selective endothelin A receptor antagonist.
2002 Aug
Asymmetric synthesis of syn- and anti-1,3-amino alcohols.
2002 Jun 12
Borane-mediated aldol cycloreduction of monoenone monoketones: diastereoselective formation of quaternary centers.
2003 Jan 10
Substrate-controlled highly diastereoselective synthesis of primary and secondary diorganozinc reagents by hydroboration/boron-zinc exchange sequence.
2003 Jun 16
Addition reactions at the 16(17) double bond of 3-methoxy-13alpha-estra-1,3,5(10),16-tetraene.
2003 Mar
Effective modular iminooxazoline (IMOX) ligands for asymmetric catalysis: [Zn(IMOX)]-promoted enantioselective reduction of ketones by catecholborane.
2003 Oct 20
Development and application of a new general method for the asymmetric synthesis of syn- and anti-1,3-amino alcohols.
2003 Sep 17
On the origin of regio- and stereoselectivity in the rhodium-catalyzed vinylarenes hydroboration reaction.
2004 Apr 16
Formation of inclusion organoactinide complexes with boron-containing macrocycles.
2004 Apr 28
Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane.
2004 Aug 4
Six- and eightfold palladium-catalyzed cross-coupling reactions of hexa- and octabromoarenes.
2004 Dec 17
In quest of factors that control the enantioselective catalytic Markovnikov hydroboration/oxidation of vinylarenes.
2004 Dec 3
Structure investigation of TiIV-BODOLates involved in the catalytic asymmetric reduction of ketones using catecholborane.
2004 Jan 5
Transition-metal-mediated synthesis of novel carbocyclic nucleoside analogues with antitumoral activity.
2004 Oct 11
Eremophilane sesquiterpenes from capsidiol.
2004 Oct 29
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 Dec 21
A convenient synthesis of immunosuppressive agent FTY720 using the petasis reaction.
2005 Jan
Photoswitching of the Lewis acidity of a catecholborane bearing an azo group based on the change in coordination number of boron.
2005 Sep 1
Development of a common fully stereocontrolled access to the medicinally important and promising prostacyclin analogues iloprost, 3-oxa-iloprost and cicaprost.
2006 Jul 17
TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration.
2006 Jul 6
Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes.
2006 May 11
Structural elucidation of a nickel boryl complex. A recyclable borylation Ni(II) reagent of bromobenzene.
2007 Nov 21
C-H bond activation of heteroarenes mediated by a half-sandwich iron complex of N-heterocyclic carbene.
2008 Dec 17
Activation of B-H bonds by an oxo-rhenium complex.
2008 Dec 21
Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series.
2008 Jan 1
Oxygen-directed intramolecular hydroboration.
2008 Jul 23
Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands.
2008 Oct 6
Highly enantioselective oxazaborolidine-catalyzed reduction of 1,3-dicarbonyl compounds: role of the additive diethylaniline.
2009 Apr 2
Total synthesis and absolute configuration of the marine norditerpenoid xestenone.
2009 Nov 24
Enantioselective, organocatalytic reduction of ketones using bifunctional thiourea-amine catalysts.
2010 Apr 16
An efficient nickel catalyst for the reduction of carbon dioxide with a borane.
2010 Jul 7
Synthesis of syn-gamma-amino-beta-hydroxyphosphonates by reduction of beta-ketophosphonates derived from L-proline and L-serine.
2010 Mar 4
Electronic tuning of a carbene center via remote chemical induction, and relevant effects in catalysis.
2010 Oct 4
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:24:40 GMT 2023
Edited
by admin
on Sat Dec 16 02:24:40 GMT 2023
Record UNII
UB69382H5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CATECHOLBORANE
MI  
Common Name English
1,3,2-BENZODIOXABOROLE
Systematic Name English
BENZCATECHINBORANE
Common 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
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3059769
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY
PUBCHEM
67506
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY
CAS
274-07-7
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-991-5
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY
FDA UNII
UB69382H5J
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY
WIKIPEDIA
CATECHOLBORANE
Created by admin on Sat Dec 16 02:24:40 GMT 2023 , Edited by admin on Sat Dec 16 02:24:40 GMT 2023
PRIMARY