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| | Dichlorophenylborane Basic information |
| | Dichlorophenylborane Chemical Properties |
| Melting point | 7 °C | | Boiling point | 66 °C11 mm Hg(lit.) | | density | 1.224 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.545(lit.) | | Fp | −5 °F | | storage temp. | 2-8°C | | form | Liquid | | color | Colorless | | Specific Gravity | 1.224 | | Water Solubility | Soluble in water (Reacts violently). | | Sensitive | Moisture Sensitive | | BRN | 2243576 | | InChI | InChI=1S/C6H5BCl2/c8-7(9)6-4-2-1-3-5-6/h1-5H | | InChIKey | NCQDQONETMHUMY-UHFFFAOYSA-N | | SMILES | B(Cl)(Cl)C1=CC=CC=C1 | | CAS DataBase Reference | 873-51-8(CAS DataBase Reference) |
| Hazard Codes | F,C | | Risk Statements | 11-34-37 | | Safety Statements | 16-26-36/37/39-45 | | RIDADR | UN 2924 3/PG 2 | | WGK Germany | 3 | | F | 10-23 | | HazardClass | 3 | | PackingGroup | II | | HS Code | 29310099 | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Flam. Liq. 2
Skin Corr. 1B |
| | Dichlorophenylborane Usage And Synthesis |
| Chemical Properties | clear colorless liquid | | History |
In 1880, Michaelis and co-workers began to investigate aryl-boranes to determine the valency of boron which was, at thetime, debated to be three or five. They reacted gaseous BCl3with diphenylmercury at elevated temperatures in a sealedtube and observed the formation of dichlorophenylborane and HgCl2. Dichlorophenylborane was isolated via distillationand was characterized by elemental analysis and conclusivefollow-up chemistry[1].
| | Uses | Catalyst for:
- Antiproliferative macrolide and cell migration inhibitor lactimidomycin
- Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions
- Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives
- Stereoselective alkylative ring opening of cyclic anhydrides
- Cross-metathesis reaction of amino derivatives with olefins
- Asymmetric acetate aldol reactions
- The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene
| | Uses | Dichlorophenylborane is widely used as a catalyst in Antiproliferative macrolide and cell migration inhibitor lactimidomycin and in enantioselective synthesis of polypeptide segments using vinylogous Mukaiyama aldol reactions and in enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives. It is a stereo selective alkylative ring opening of cyclic anhydrides and in cross-metathesis reaction of amino derivatives with olefines. | | reaction suitability | reagent type: reductant | | References | [1] Sarina M. Berger, Prof.Dr. Todd B. Marder, Matthias Ferger. “Synthetic Approaches to Triarylboranes from 1885 to 2020.” Chemistry - A European Journal 27 24 (2021): 7043–7058.
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| | Dichlorophenylborane Preparation Products And Raw materials |
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