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| | Cyclopropylboronic acid Basic information |
| | Cyclopropylboronic acid Chemical Properties |
| Melting point | 90-95 °C (lit.) | | Boiling point | 205.1±23.0 °C(Predicted) | | density | 1.11±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | DMSO | | pka | 10.49±0.20(Predicted) | | form | Powder | | color | white | | Sensitive | moisture sensitive | | InChI | InChI=1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2 | | InChIKey | WLVKDFJTYKELLQ-UHFFFAOYSA-N | | SMILES | C1CC1B(O)O | | CAS DataBase Reference | 411235-57-9(CAS DataBase Reference) |
| Hazard Codes | Xn,T | | Risk Statements | 22-36-61-60-36/37/38 | | Safety Statements | 26-36-45-53-37/39 | | WGK Germany | 3 | | TSCA | No | | HazardClass | IRRITANT, IRRITANT-HARMFUL | | HS Code | 29319090 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Repr. 1B |
| | Cyclopropylboronic acid Usage And Synthesis |
| Chemical Properties | White to off-white powder | | Uses | Cyclopropylboronic Acid is an organoboronic acid commonly used in highly efficient Suzuki coupling reactions. | | Uses | Reagent used for• ;Microwave-assisted copper(II)-catalyzed N-cyclopropylation1• ;Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes2• ;Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid3• ;Palladium(0)-catalyzed cyclopropane C-H bond functionalization4• ;Palladium-catalyzed decarboxylative coupling5• ;Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes6• ;Palladium-catalyzed Suzuki coupling reaction7Reagent used in Preparation of• ;Diaryl ketones by arylation | | Uses | suzuki reaction | | Synthesis | Cyclopropylmagnesium bromide (0.5 M in THF, 25 mL, 12.5 mmol) was added dropwise to a stirred solution of trimethylborate (1.69 g, 1.81 mL, 16.25 mmol) in tetrahydrofuran (7 mL) under nitrogen protection at -78°C. A white precipitate was observed during the reaction. A white precipitate was observed to form during the reaction. after 1 h, the reaction system was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction was quenched with 2.0 N aqueous hydrochloric acid (20 mL) and the mixture was stirred for 1 hr. Subsequently, the reaction mixture was extracted with dichloromethane (15 mL) and the aqueous phase was back-extracted with deionized water (2 x 15 mL). All aqueous phases were combined and extracted with methyl tert-butyl ether (4 x 40 mL). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to give a white solid product. Two recrystallizations were carried out via a solvent mixture of dichloromethane and hexane, resulting in 252-297 mg of white solid product in 27% yield. The product was characterized by NMR hydrogen spectroscopy (250 MHz, CDCl3): δ 0.56-0.50 (2H, m, CH2), 0.42-0.40 (2H, m, CH2), -0.08 to -0.20 (1H, m, CH). | | References | [1] Patent: WO2004/56788, 2004, A1. Location in patent: Page 51 |
| | Cyclopropylboronic acid Preparation Products And Raw materials |
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