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731528

Sigma-Aldrich

trans-2-Ethoxyvinylboronic acid pinacol ester

95%

Synonym(s):

(E)-2-(2-Ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, (E)-2-Ethoxyvinylboronic acid pinacol ester

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About This Item

Empirical Formula (Hill Notation):
C10H19BO3
CAS Number:
1201905-61-4
Molecular Weight:
198.07
MDL number:
MFCD09998813
UNSPSC Code:
12352103
PubChem Substance ID:
329764663
NACRES:
NA.22

Quality Level

100

Assay

95%

form

liquid

refractive index

n20/D 1.447

density

0.935 g/mL at 25 °C

functional group

ether

storage temp.

2-8°C

SMILES string

CCO\C=C\B1OC(C)(C)C(C)(C)O1

InChI

1S/C10H19BO3/c1-6-12-8-7-11-13-9(2,3)10(4,5)14-11/h7-8H,6H2,1-5H3/b8-7+

InChI key

MRAYNLYCQPAZJN-BQYQJAHWSA-N

Application

trans-2-Ethoxyvinylboronic acid pinacol ester is a boronic ester commonly used in Suzuki-Miyaura cross-coupling.
This reaction is a key step to synthesize:
  • Azaindole and diazaindoles from chloroamino-N-heterocycles.
  • Doryanine and its derivatives from 2-bromobenzoic acid.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

188.1 °F

Flash Point(C)

86.7 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM9030
SHBK5988
SHBH2831V
SHBF9370V
SHBD6646V

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Structure-and reactivity-based development of covalent inhibitors of the activating and gatekeeper mutant forms of the epidermal growth factor receptor (EGFR).
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Total Synthesis of the Illicium-Derived Sesquineolignan Simonsol C.
Nugent, Jeremy et al.
Organic Letters, 18(15), 3798-3801 (2016)
Two-step synthesis of aza-and diazaindoles from chloroamino-N-heterocycles using ethoxyvinylborolane.
Whelligan, Daniel K et al.
The Journal of Organic Chemistry, 75(1), 11-15 (2009)
Efficient and rapid synthesis of N-substituted isoquinolin-1-ones under mild conditions: Facile access to doryanine derivatives
Takwale AD, et al.
Tetrahedron Letters, 60(18), 1259-1261 (2019)

Articles

Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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