• USA Home
  • 597988 - Cyclopropylboronic acid

EMAIL THIS PAGE TO A FRIEND
597988 Sigma-Aldrich

Cyclopropylboronic acid

Synonym: Cyclopropaneboronic acid

  • CAS Number 411235-57-9

  • Empirical Formula (Hill Notation) C3H7BO2

  • Molecular Weight 85.90

  •  MDL number MFCD04038750

  •  PubChem Substance ID 24881728

  •  NACRES NA.22

Purchase

Properties

Related Categories Alkyl and Aryl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
Quality Level   100
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

Description

Application

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

Packaging

1, 5, 25 g in glass bottle

Other Notes

Contains varying amounts of anhydride

May contain 3-5% cyclopropanol

May contain 5-10% boric acid

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number

Certificate of Origin (COO)

Please Enter a Lot Number

Frequently Asked Questions

How does the storage temperature relate to shipping conditions?
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. See Shipping and Storage for more information.
Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
How do I find price and availability?
There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 or view local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
What is the pKa of Product 597988, Cyclopropylboronic acid?
The pKa of most boronic acids is approximately 9.
What is it about boronic acids that makes them acidic?
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.
What compounds are formed when boronic acids degrade?
Boronic acids are typically very stable. However, if degradation occurs, boronic acid will degrade to corresponding alcohol and boric acid.
What is the solubility for Product 597988, Cyclopropylboronic acid?
Product No. 597988 should be soluble in methanol at 0.1g in 30 mL (approximately 3 mg/mL).
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
Show more questions
Protocols & Articles

Articles

Boronic Acids - ChemFiles 2007

Most boronic acids readily undergo dehydration reactions to give a cyclic (trimer) anhydride. Our selection of boronic acids may contain varying amounts of this cyclic anhydride. Fortunately, the aci...
ChemFiles 2007, 7.7, 3.
Keywords: Coupling reactions, Dehydration reaction, Suzuki coupling

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

28982 Curcumin solution, ~0.1 % (w/v) (in ethanol with 2M HCl (99:1 v/v)), for TLC derivatization
06693 Timestrip Plus -20 °C

Technical Service:

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

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?