CATECHOLBORANE

Catecholborane is an organoboron compound commonly used in organic synthesis as a selective hydroborating agent.
Catecholborane is known for its ability to add across carbon-carbon multiple bonds with high regioselectivity and stereoselectivity.
Catecholborane is used as a mild and stable boron reagent in both academic and industrial applications, particularly in pharmaceuticals and materials chemistry.

CAS Number: 274-07-7
EC Number: 205-985-3
Molecular Formula: C6H5BO2
Molecular Weight: 123.91 g/mol

Synonyms: Catecholborane, Boronic Acid, Catechol Ester, HBcat, 1,3,2-Benzodioxaborole, o-Benzenediolborane, Boranate Ester, Catechol Boronic Ester, Hydroxyphenylborane, Hydroboration Reagent, Boron-Catechol Complex, Catecholborane, Catchelborane, Catecholatoborane, Pyrocatecholborane, HBcat, 1,3,2-Benzodioxaborole, Benzo[1,3,2]dioxaborole, Benzo[d][1,3,2]dioxaborole, Benzcatechinborane, 7,9-dioxa-8λ²-borabicyclo[4.3.0]nona-1,3,5-triene, C₆H₅BO₂, CAS 274‑07‑7, EC 205‑991‑5, PubChem CID 6327445, ChemSpider 10617125, InChIKey CENMEJUYOOMFFZ‑UHFFFAOYSA‑N, UB69382H5J, RARECHEM AK VD 0002, Catechol borane in THF, HBcat solution, 50 % w/w Catecholborane in toluene, 1.0 M Catecholborane in THF, 98 % Catecholborane, 99 % Catecholborane, ≥99.9 % Catecholborane, Reagent-grade Catecholborane, Analytical-grade Catecholborane, Technical-grade Catecholborane, Food-grade Catecholborane, Pharma-grade Catecholborane

APPLICATIONS

Catecholborane is widely used in hydroboration reactions to convert alkenes into organoboron intermediates.
Catecholborane is employed in the regioselective addition of boron across alkynes for use in further functional group transformations.
Catecholborane is utilized in asymmetric synthesis when paired with chiral catalysts.

Catecholborane is applied in the pharmaceutical industry to prepare intermediates for drug development.
Catecholborane is used to synthesize biologically active molecules that require specific stereochemistry.
Catecholborane is involved in the preparation of boron-containing compounds used in boron neutron capture therapy (BNCT).

Catecholborane is used in organic electronics to introduce boron functionality into polymer backbones.
Catecholborane serves as a precursor in the synthesis of boronate esters used in Suzuki-Miyaura coupling reactions.
Catecholborane is utilized in the functionalization of graphene and other carbon-based materials.

Catecholborane is applied in academic research as a standard reagent for hydroboration-oxidation studies.
Catecholborane is used in polymer chemistry to modify unsaturated monomers.
Catecholborane is employed in developing catalysts and ligands that contain boron centers.

Catecholborane is used in total synthesis routes for natural products and complex organic molecules.
Catecholborane is involved in the introduction of boron moieties in fluorescent labeling and imaging agents.
Catecholborane is used in agrochemical synthesis to develop boron-based growth enhancers and protective agents.

Catecholborane is incorporated into synthesis protocols for nonionic surfactants containing boron.
Catecholborane is utilized in the design of boron-based sensors and responsive materials.
Catecholborane is applied in fuel research for the development of boron-based energy storage compounds.

Catecholborane is used in the synthesis of flame retardants containing boron for plastic and textile applications.
Catecholborane is employed in producing intermediates for liquid crystal materials.
Catecholborane is used in academic laboratories to teach principles of chemoselectivity and functional group compatibility.

Catecholborane is included in the preparation of nanostructured boron-containing frameworks.
Catecholborane is utilized in synthesizing precursors for boronic acid-functionalized biomolecules.
Catecholborane is used in the modification of dendrimers for advanced materials and drug delivery systems.

Catecholborane is used in organic synthesis for hydroboration of alkenes.
Catecholborane is employed in enantioselective reductions of carbonyl compounds.
Catecholborane is used to convert alkynes into cis-alkenes via syn-addition.

Catecholborane is utilized in the synthesis of boron-containing pharmaceuticals.
Catecholborane is applied in catalytic asymmetric reductions with chiral auxiliaries.

Catecholborane is used in the preparation of secondary and tertiary alcohols.
Catecholborane is employed in the formation of vinyl boranes from alkynes.
Catecholborane is used in Suzuki-Miyaura cross-coupling reactions after conversion to boronic acids.

Catecholborane is used to produce organoboron compounds for medicinal chemistry.
Catecholborane is utilized in hydride transfer reactions in fine chemical synthesis.

Catecholborane is applied in boron neutron capture therapy research for boron delivery agents.
Catecholborane is used in materials science to introduce boron into polymeric structures.

Catecholborane is employed in reducing oximes and imines to amines.
Catecholborane is used in stereoselective synthesis of allylic alcohols.

Catecholborane is applied in transition-metal-catalyzed hydroboration reactions.
Catecholborane is used in total synthesis of natural products.

Catecholborane is employed in the development of novel boron ligands.
Catecholborane is used to generate boron-containing heterocycles.
Catecholborane is utilized in reducing nitro compounds under mild conditions.

Catecholborane is applied in chemoselective reductions of multiple functional groups.
Catecholborane is used in the synthesis of radiolabeled boron compounds for PET imaging.

Catecholborane is used in laboratory-scale hydrogenation processes.
Catecholborane is used to study reaction mechanisms in organoboron chemistry.
Catecholborane is applied in the formation of borate esters.

Catecholborane is used in making boron-functionalized ligands for catalysis.
Catecholborane is used in regioselective hydroboration of unsaturated compounds.

Catecholborane is employed in the synthesis of anti-cancer boron compounds.
Catecholborane is used to produce boron-based flame retardants.
Catecholborane is utilized in doping processes for semiconductors.

Catecholborane is applied in reducing carbonyl groups in carbohydrates.
Catecholborane is used in the synthesis of organoboron polymers.

Catecholborane is employed in cross-coupling reactions via boronate intermediates.
Catecholborane is used in academic research focused on selective reductions.
Catecholborane is used to prepare stable boron-carbon bonds.

Catecholborane is applied in derivatization of steroidal molecules.
Catecholborane is used in the study of steric effects in hydroboration.

Catecholborane is employed in synthesis of high-purity alcohol intermediates.
Catecholborane is used in the generation of alkyl boranes for industrial processes.
Catecholborane is used in stereoselective transformations in chiral chemistry.

Catecholborane is utilized in catalysis with rhodium and iridium complexes.
Catecholborane is used in hydroboration of dienes and enynes.

Catecholborane is applied in hydride transfer processes for fine chemicals.
Catecholborane is used in bench-scale pilot studies for boron-based drugs.
Catecholborane is used in boron addition reactions to carbon–carbon double bonds.

Catecholborane is employed to synthesize intermediates for agrochemicals.
Catecholborane is used in development of reagents for asymmetric synthesis.

Catecholborane is used in the formation of stable boron–oxygen bonds.
Catecholborane is utilized in boron-based protecting group strategies.

Catecholborane is applied in the research of electron-deficient boron reagents.
Catecholborane is used in ligand design for organometallic catalysts.

DESCRIPTION

Catecholborane is a colorless to pale yellow liquid with a slightly aromatic odor.
Catecholborane consists of a boron atom coordinated with catechol (1,2-dihydroxybenzene), forming a five-membered heterocycle.
Catecholborane is a reactive, yet more stable and selective alternative to diborane or borane-THF complexes.

Catecholborane acts as a mild hydroborating reagent, providing clean and controlled additions to unsaturated compounds.
Catecholborane is typically used in anhydrous solvents under inert atmosphere to prevent hydrolysis.
Catecholborane is highly valued for its regioselectivity, producing anti-Markovnikov products in hydroboration reactions.

Catecholborane offers a safer and more manageable alternative to more volatile boranes.
Catecholborane is sensitive to air and moisture and should be handled in controlled environments.
Catecholborane can be stored for extended periods if properly sealed and kept away from oxidizers.

Catecholborane is an organoboron compound composed of catechol and borane.
Catecholborane appears as a colorless to light yellow liquid with high reactivity.

Catecholborane is a valuable reagent in organic synthesis, particularly for hydroboration reactions.
Catecholborane is sensitive to moisture and should be handled under inert conditions.

Catecholborane reacts readily with alkenes and alkynes to form boron-containing intermediates.
Catecholborane is often used in asymmetric synthesis due to its stereoselective properties.

Catecholborane serves as a source of nucleophilic hydride in reduction reactions.
Catecholborane can be converted to more stable boron derivatives like boronic acids.

Catecholborane is preferred for reactions requiring mild and selective boron addition.
Catecholborane plays an important role in academic and industrial research in synthetic chemistry.

PROPERTIES

Chemical Name: Catecholborane
Molecular Formula: C6H5BO2
Molecular Weight: 123.91 g/mol
Appearance: Colorless to pale yellow liquid
Odor: Slightly aromatic
Boiling Point: ~84°C at 10 mmHg
Melting Point: Not applicable
Solubility: Soluble in organic solvents (e.g., THF, diethyl ether, toluene); reacts with water
Reactivity: Reacts violently with water, alcohols, and oxidizing agents
Flash Point: ~35°C
Density: ~1.13 g/cm³
Storage: Store under inert atmosphere, in a tightly sealed container
Stability: Stable under inert, dry conditions; decomposes with moisture

FIRST AID

Inhalation:
Remove to fresh air immediately.
Provide oxygen if breathing is difficult.
Seek medical attention if symptoms persist.

Skin Contact:
Immediately wash with soap and plenty of water.
Remove contaminated clothing.
Get medical attention in case of persistent irritation.

Eye Contact:
Flush eyes thoroughly with water for at least 15 minutes.
Remove contact lenses if present.
Seek medical attention immediately.

Ingestion:
Do not induce vomiting.
Rinse mouth with water.
Seek immediate medical help.

Note to Physicians:
Treat symptomatically.
Catecholborane may release toxic fumes if decomposed.

HANDLING AND STORAGE

Handling:
Handle under inert atmosphere (e.g., nitrogen or argon).
Avoid contact with water or moisture.
Wear protective gloves, goggles, and clothing.
Use in a fume hood with appropriate precautions.

Storage:
Store in a tightly sealed container under an inert gas.
Keep away from heat, sparks, open flame, and incompatible materials.
Avoid contact with air and moisture.
Recommended storage temperature: 2–8°C (refrigerated).

Spill Response:
Absorb with dry inert material (e.g., vermiculite or sand).
Do not use water.
Place in chemical waste container and ventilate the area.