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| CATECHOLBORANE Basic information |
| Product Name: | CATECHOLBORANE | | Synonyms: | Benzo[d][1,3,2]dioxaborole(1.0M);CATECHOLBORANE;1,3,2-BENZODIOXABOROLE;RARECHEM AK VD 0002;Catecholborane, 1.0 M solution in THF;Catecholborane, Benzo[d][1,3,2]dioxaborole;Catecholborane, 1.0 M solution in THF, J&KSeal;Benzcatechinborane | | CAS: | 274-07-7 | | MF: | C6H5BO2 | | MW: | 119.91 | | EINECS: | 205-991-5 | | Product Categories: | Boranes;Boronic Acids and Derivatives;Borylation Reagents;Chemical Synthesis;Organometallic Reagents;Synthetic Reagents;BoranesOrganometallic Reagents;Boronic Acids and Derivatives;Borylation Reagents;Reduction;Synthetic Reagents | | Mol File: | 274-07-7.mol |
| CATECHOLBORANE Chemical Properties |
| Melting point | 12 °C(lit.) | | Boiling point | 50 °C50 mm Hg(lit.) | | density | 1.125 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.507(lit.) | | Fp | 36 °F | | storage temp. | 2-8°C | | solubility | Miscible with diethyl ether, tetrahydrofuran, dichloromethane, chloroform, carbon tetrachloride, toluene, and benzene. | | form | liquid | | color | Hazy Colourless | | Water Solubility | Reacts with water. | | Sensitive | Moisture Sensitive | | BRN | 972072 | | InChIKey | CENMEJUYOOMFFZ-UHFFFAOYSA-N | | CAS DataBase Reference | 274-07-7(CAS DataBase Reference) | | EPA Substance Registry System | 1,3,2-Benzodioxaborole (274-07-7) |
| CATECHOLBORANE Usage And Synthesis |
| Chemical Properties | CATECHOLBORANE is clear colorless solution
| | Uses | CATECHOLBORANE is used in the transition metal catalyzed hydroboration of alkenes.1,2,3
| | Uses | Catecholborane is used to prepare B-alkylcatecholboranes. It finds application for the preparation of amides and macrocyclic lactams from carboxylic acids. It is used as a stereoselective reducing agent to convert beta-hydroxy ketones to syn 1,3-diols. Further, it reacts with alkyne through hydroboration to form trans vinyl borane, which is a precursor to Suzuki reaction. | | Purification Methods | It is a moisture-sensitive flammable liquid which is purified by distillation in a vacuum under a N2 atmosphere and stored under N2 at 0-4o. It liberates H2 when added to H2O or MeOH. A solution in THF, after 25hours at 25o, has residual hydride of 95% (under N2) and 80% (under air) [Brown & Gupta J Am Chem Soc 97 5249 1975]. |
| CATECHOLBORANE Preparation Products And Raw materials |
| Raw materials | Tetrahydrofuran-->Catechol-->Borane-tetrahydrofuran complex | | Preparation Products | E-PHENYLETHENYLBORONIC ACID-->1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE-->tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate |
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