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576638

Sigma-Aldrich

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
Pricing and availability is not currently available.

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

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[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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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
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)
Tetrahydrobenzothiophene derivatives: conformationally restricted inhibitors of type II dehydroquinase.
Sonia Paz et al.
ChemMedChem, 6(2), 266-272 (2011-01-29)
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)
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

Questions

1–6 of 6 Questions  
  1. What compounds are formed when boronic acids degrade?

    1 answer
    1. Boronic acids are typically very stable. However, if degradation occurs, Boronic acid will degrade to corresponding alcohol and boric acid.

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  2. Is the cis isomer present in Product 576638, trans-1-Propen-1-ylboronic acid?

    1 answer
    1. Product No. 576638 may contain up to 10 wt% of the cis isomer.

      Helpful?

  3. What is the pKa of Product 576638, trans-1-Propen-1-ylboronic acid?

    1 answer
    1. The pKa of most boronic acids is approximately 9.

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  4. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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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  5. How does the storage temperature relate to shipping conditions?

    1 answer
    1. 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.

      Helpful?

  6. What is it about boronic acids that makes them acidic?

    1 answer
    1. 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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