Boronic acids are typically very stable. However, if degradation occurs, Boronic acid will degrade to corresponding alcohol and boric acid.
576638
trans-1-Propen-1-ylboronic acid
≥95.0%
Synonym(s):
(E)-1-Propen-1-ylboronic acid, (E)-Prop-1-enylboronic acid, trans-1-Propeneboronic acid, trans-1-Propenylboronic acid, trans-Propenylboronic acid
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About This Item
Linear Formula:
CH3CH=CHB(OH)2
CAS Number:
Molecular Weight:
85.90
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥95.0%
impurities
~10 wt. % cis-isomer
mp
123-127 °C (lit.)
storage temp.
2-8°C
SMILES string
[H]\C(C)=C(\[H])B(O)O
InChI
1S/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2+
InChI key
CBMCZKMIOZYAHS-NSCUHMNNSA-N
Related Categories
Application
Reactant for:
Reactant for preparation of:
- 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
Reactant for preparation of
- Palladium-phosphine-catalyzed Suzuki-Miyaura coupling reactions[1][2][3]
- Cu(II)-mediated Ullmann-type coupling[4]
- Palladium-catalyzed Sonogashira cross-coupling[5]
Reactant for preparation of
- Alkynylphenoxyacetic acids as DP2 receptor antagonists for treatment of allergic inflammatory diseases[6]
- Tetrahydrobenzothiophenes as conformationally restricted enol-mimic inhibitors of type II dehydroquinase via Paal-Knorr synthesis involving Suzuki coupling[7]
- Highly substituted benzannulated cyclooctanol derivatives by samarium diiodide-mediated cyclization[8]
- Stereospecific dienes via nickel-catalyzed three-component reductive coupling with alkynes and enones[9]
Other Notes
Contains varying amounts of anhydride
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Chun-Ming Yang et al.
Organic letters, 12(16), 3610-3613 (2010-08-14)
A highly regio- and stereoselective nickel-catalyzed three-component coupling of alkynes with enones and alkenyl boronic acids to afford highly substituted 1,3-dienes is described. The reaction can also be extended to cyclization of enynes with coupling to alkenyl boronic acids. A
Total synthesis of rodgersinol: a survey of the Cu(II)-mediated coupling of ortho-substituted phenols
Jung, J.-W.; et al.
Tetrahedron, 66, 6826-6831 (2010)
A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
Fuwa, H.; et al.
Tetrahedron, 67, 4995-5010 (2011)
The preparation of substituted pyrazoles from β,β-dibromo-enones by a tandem condensation/Suzuki-Miyaura cross-coupling process
Beltran-Rodil, S.; et al.
Synlett, 4, 602-606 (2010)
Ming-Bo Zhou et al.
The Journal of organic chemistry, 75(16), 5635-5642 (2010-08-14)
Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)(2) and Ag(2)O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding
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What compounds are formed when boronic acids degrade?
1 answer-
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Is the cis isomer present in Product 576638, trans-1-Propen-1-ylboronic acid?
1 answer-
Product No. 576638 may contain up to 10 wt% of the cis isomer.
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What is the pKa of Product 576638, trans-1-Propen-1-ylboronic acid?
1 answer-
The pKa of most boronic acids is approximately 9.
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What is the Department of Transportation shipping information for this product?
1 answer-
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.
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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 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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