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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

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
  • 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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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)
Jakub Saadi et al.
Beilstein journal of organic chemistry, 6, 1229-1245 (2011-02-02)
A series of γ-oxo esters suitably substituted with various styrene subunits was subjected to samarium diiodide-induced 8-endo-trig cyclizations. Efficacy, regioselectivity and stereoselectivity of these reactions via samarium ketyls strongly depend on the substitution pattern of the attacked alkene moiety. The

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