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576638

Sigma-Aldrich

trans-1-Propen-1-ylboronic acid

≥95.0%

Synonyme(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

Formule linéaire :
CH3CH=CHB(OH)2
Numéro CAS:
7547-97-9
Poids moléculaire :
85.90
Numéro MDL:
MFCD02179501
Code UNSPSC :
12352103
ID de substance PubChem :
24880870
Nomenclature NACRES :
NA.22

Pureté

≥95.0%

Impuretés

~10 wt. % cis-isomer

Pf

123-127 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

[H]\C(C)=C(\[H])B(O)O

InChI

1S/C3H7BO2/c1-2-3-4(5)6/h2-3,5-6H,1H3/b3-2+

Clé InChI

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

Autres remarques

Contains varying amounts of anhydride

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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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
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)
Daohong Yu et al.
The Journal of organic chemistry, 77(4), 1798-1804 (2012-01-31)
A selective palladium-catalyzed Suzuki-Miyaura coupling reaction of polyfluorophenyl oxazolines through ortho C-F activation is described. It was found that reactions with DPPF as the ligand occurred much faster than those with other ligands. A variety of arylboronic acids including challenging
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