Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

597988

Sigma-Aldrich

Cyclopropylboronic acid

Synonym(s):

Cyclopropaneboronic acid

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Facile synthesis of aryl(het)cyclopropane catalyzed by palladacycle
Zhang, M.; et al.
Tetrahedron, 68, 900-905 (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
Xiao Chen et al.
Journal of the American Chemical Society, 128(39), 12634-12635 (2006-09-28)
Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated.
Microwave-assisted N-cyclopropylation of pyridinols with cyclopropyl boronic acid
Tambe, Y. B.; et al.
Synthetic Communications, 42, 1341-1348 (2012)
Ni- and Cu-catalyzed coupling reactions using 2-(4,5-dihydro-1H-imidazo-2-yl)phenol as a versatile phosphine-free ligand
Haneda, S.; Sudo, K.; Hayashi, M.
Heterocycles, 84, 569-575 (2012)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service