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597988

Sigma-Aldrich

Cyclopropylboronic acid

Synonym(s):

Cyclopropaneboronic acid

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About This Item

Empirical Formula (Hill Notation):
C3H7BO2
CAS Number:
411235-57-9
Molecular Weight:
85.90
MDL number:
MFCD04038750
UNSPSC Code:
12352103
PubChem Substance ID:
24881728
NACRES:
NA.22

form

solid

mp

90-95 °C (lit.)

storage temp.

−20°C

SMILES string

OB(O)C1CC1

InChI

1S/C3H7BO2/c5-4(6)3-1-2-3/h3,5-6H,1-2H2

InChI key

WLVKDFJTYKELLQ-UHFFFAOYSA-N

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Application

Boronic acid component in a study of carbon-hydrogen bond alkylation in the presence of Pd(II), Ag(I) and benzoquinone.
Cu-mediated N-cyclopropanation
Reagent used for
  • Microwave-assisted copper(II)-catalyzed N-cyclopropylation
  • Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes
  • Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid
  • Palladium(0)-catalyzed cyclopropane C-H bond functionalization
  • Palladium-catalyzed decarboxylative coupling
  • Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes
  • Palladium-catalyzed Suzuki coupling reaction

Reagent used in Preparation of
  • Diaryl ketones by arylation of arylboronic acids with aromatic aldehydes catalyzed by Cu(OTf)2 and Xantphos
  • Aminothiazolylpyrrolidine-based tartrate diamides as TACE inhibitors to treat inflammatory disorders and cancer

Other Notes

Contains varying amounts of anhydride
May contain 3-5% cyclopropanol
May contain 5-10% boric acid

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Sébastien Bénard et al.
The Journal of organic chemistry, 73(16), 6441-6444 (2008-07-10)
Reaction of azoles, amides, and sulfonamides in dichloroethane with readily available cyclopropylboronic acid in the presence of copper acetate and sodium carbonate afforded the N-cyclopropyl derivatives in good to excellent yields.
Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes
Kubota, A.; Sanford, M. S.
Synthesis, 16, 2579-2589 (2011)
Tetrahedron Letters, 43, 6987-6990 (2002)
Microwave-assisted N-cyclopropylation of pyridinols with cyclopropyl boronic acid
Tambe, Y. B.; et al.
Synthetic Communications, 42, 1341-1348 (2012)
Chaoyang Dai et al.
Bioorganic & medicinal chemistry letters, 21(10), 3172-3176 (2011-04-05)
TNF-α converting enzyme (TACE) inhibitors are promising agents to treat inflammatory disorders and cancer. We have investigated novel tartrate diamide TACE inhibitors where the tartrate core binds to zinc in a unique tridentate fashion. Incorporating (R)-2-(2-N-alkylaminothiazol-4-yl)pyrrolidines into the left hand
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