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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

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1 of 4

This Item
06536C80687C80857
assay

≥98.0% (GC)

assay

≥95.0% (GC)

assay

97%

assay

≥99%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

density

1.05 g/cm3 at 20 °C

density

1.05 g/mL at 25 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

density

-

storage temp.

2-30°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

form

liquid

form

-

form

liquid

form

crystals

mp

-8 °C

mp

−9-−4 °C (lit.)

mp

−9-−4 °C (lit.)

mp

132-135 °C (lit.)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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    Jeffrey S Bandar et al.
    Journal of the American Chemical Society, 134(12), 5552-5555 (2012-03-16)
    Cyclopropenimines are shown to be a highly effective new class of enantioselective Brønsted base catalysts. A chiral 2,3-bis(dialkylamino)cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25

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