| Identification | More | [Name]
Cyclopropylboronic acid | [CAS]
411235-57-9 | [Synonyms]
AKOS BRN-0457
CYCLOPROPYLBORONIC ACID
Cyclopropylboronic acid,monohydrate
CYCLOROPYLBORONIC ACID
Boronic acid, cyclopropyl-(9CI)
Cyclopropylboronic
Cyclopropylboronic acid 95%
Chemical Name: Cyclopropylboronic acid
Cyclopropylboronic acid, tech. 85% | [EINECS(EC#)]
609-890-0 | [Molecular Formula]
C3H7BO2 | [MDL Number]
MFCD04038750 | [Molecular Weight]
85.9 | [MOL File]
411235-57-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
90-95 °C (lit.) | [Boiling point ]
205.1±23.0 °C(Predicted) | [density ]
1.11±0.1 g/cm3(Predicted) | [storage temp. ]
Store below-20 | [solubility ]
DMSO | [form ]
Powder | [pka]
10.49±0.20(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [TSCA ]
No | [HazardClass ]
IRRITANT, IRRITANT-HARMFUL | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [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 |
|
|