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576638 Sigma-Aldrich

trans-1-Propen-1-ylboronic acid

≥95.0%

Synonym: (E)-Prop-1-enylboronic acid, (E)-1-Propen-1-ylboronic acid, trans-1-Propeneboronic acid, trans-1-Propenylboronic acid, trans-Propenylboronic acid

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Properties

Related Categories Alkenyl Boronic Acids, Boronic Acids, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
InChI Key   CBMCZKMIOZYAHS-NSCUHMNNSA-N
assay   ≥95.0%
impurities   ~10 wt. % cis-isomer
mp   123-127 °C (lit.)
storage temp.   2-8°C

Description

Application

Reactant for:
• Palladium-phosphine-catalyzed Suzuki-Miyaura coupling reactions
• Cu(II)-mediated Ullmann-type coupling

Reactant for preparation of:
• Alkynylphenoxyacetic acids as DP2 receptor antagonists for treatment of allergic inflammatory diseases
• Tetrahydrobenzothiophenes as conformationally restricted enol-mimic inhibitors of type II dehydroquinase via Paal-Knorr synthesis involving Suzuki coupling
• Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-mediated cyclization
• Stereospecific dienes via nickel-catalyzed three-component reductive coupling with alkynes and enones

Reactant for
• Palladium-phosphine-catalyzed Suzuki-Miyaura coupling reactions
• Cu(II)-mediated Ullmann-type coupling
• Palladium-catalyzed Sonogashira cross-coupling

Reactant for preparation of
• Alkynylphenoxyacetic acids as DP2 receptor antagonists for treatment of allergic inflammatory diseases
• Tetrahydrobenzothiophenes as conformationally restricted enol-mimic inhibitors of type II dehydroquinase via Paal-Knorr synthesis involving Suzuki coupling
• Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-mediated cyclization
• Stereospecific dienes via nickel-catalyzed three-component reductive coupling with alkynes and enones

Packaging

1, 5 g in glass bottle

Other Notes

Contains varying amounts of anhydride

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

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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 orview 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 576638, trans-1-Propen-1-ylboronic 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.
Is the cis isomer present in Product 576638, trans-1-Propen-1-ylboronic acid?
Product No. 576638 may contain up to 10 wt% of the cis isomer.
My question is not addressed here, how can I contact Technical Service for assistance?
Ask a Scientist here.
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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

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