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597988
Cyclopropylboronic acid
Synonym(s):
Cyclopropaneboronic acid
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1 G
$82.09
5 G
$213.00
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$779.00
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1 G
$82.09
5 G
$213.00
25 G
$779.00
About This Item
Empirical Formula (Hill Notation):
C3H7BO2
CAS Number:
Molecular Weight:
85.90
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
solid
Quality Level
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.[1]
Cu-mediated N-cyclopropanation[2]
Reagent used for
Reagent used in Preparation of
- Microwave-assisted copper(II)-catalyzed N-cyclopropylation[3]
- Nickel- and copper-catalyzed Suzuki-Miyaura coupling reaction of arenes[4]
- Palladacycle-catalyzed Suzuki-cross coupling of aryl halides with cyclopropylboronic acid[5]
- Palladium(0)-catalyzed cyclopropane C-H bond functionalization[6]
- Palladium-catalyzed decarboxylative coupling[7]
- Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes[8]
- Palladium-catalyzed Suzuki coupling reaction[9]
Reagent used in Preparation of
Other Notes
Contains varying amounts of anhydride
May contain 3-5% cyclopropanol
May contain 5-10% boric acid
signalword
Danger
hcodes
Hazard Classifications
Repr. 1B
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Customers Also Viewed
Palladium-catalyzed ligand-directed oxidative functionalization of cyclopropanes
Kubota, A.; Sanford, M. S.
Synthesis, 16, 2579-2589 (2011)
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.
Tetrahedron Letters, 43, 6987-6990 (2002)
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
Microwave-assisted N-cyclopropylation of pyridinols with cyclopropyl boronic acid
Tambe, Y. B.; et al.
Synthetic Communications, 42, 1341-1348 (2012)
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What is the Department of Transportation shipping information for this product?
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What is it about boronic acids that makes them acidic?
1 answer-
Boronic acids have a vacant p orbital. Therefore, despite the presence of two hydroxyl groups, the acidic character of most Boronic acids is that of a Lewis acid.
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What compounds are formed when boronic acids degrade?
1 answer-
Boronic acids are typically very stable. However, if degradation occurs, boronic acid will degrade to corresponding alcohol and boric acid.
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How does the storage temperature relate to shipping conditions?
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The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment.
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What is the solubility for Product 597988, Cyclopropylboronic acid?
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Product No. 597988 should be soluble in methanol at 0.1g in 30 mL (approximately 3 mg/mL).
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What is the pKa of Product 597988, Cyclopropylboronic acid?
1 answer-
The pKa of most boronic acids is approximately 9.
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