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721352

Sigma-Aldrich

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

97%

Synonym(s):

2-(3,6-Dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C11H19BO3
CAS Number:
287944-16-5
Molecular Weight:
210.08
MDL number:
MFCD11052631
UNSPSC Code:
12352103
PubChem Substance ID:
329763842
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

63-67 °C

functional group

ether

storage temp.

2-8°C

SMILES string

CC1(C)OB(OC1(C)C)C2=CCOCC2

InChI

1S/C11H19BO3/c1-10(2)11(3,4)15-12(14-10)9-5-7-13-8-6-9/h5H,6-8H2,1-4H3

InChI key

DOSGEBYQRMBTGS-UHFFFAOYSA-N

Application

3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester can be used:
  • To prepare 1,2-dihydro-2-oxopyridine based endocannabinoid system (ECS) modulators.
  • As an intermediate in the synthesis of embryonic ectoderm development (EED) inhibitors.
  • To prepare pyrrolotriazine based IRAK4 inhibitors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1743
MKCL4188
MKCD5727
MKBW6137V
MKBT0424V

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Modification on the 1, 2-dihydro-2-oxo-pyridine-3-carboxamide core to obtain multi-target modulators of endocannabinoid system
Gado F, et al.
Bioorganic Chemistry, 94, 103353-103353 (2020)
EEDi-5285: An Exceptionally Potent, Efficacious, and Orally Active Small-Molecule Inhibitor of Embryonic Ectoderm Development
Rej RK, et al.
Journal of medicinal chemistry, 63(13), 7252-7267 (2020)
Optimization of permeability in a series of pyrrolotriazine inhibitors of IRAK4
Degorce SL, et al.
Bioorganic & Medicinal Chemistry, 26(4), 913-924 (2018)

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