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)

Safety Information

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

MSDS

• Language:English Provider:SigmaAldrich

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

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