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709875

Sigma-Aldrich

3-Methoxythiophene-2-boronic acid pinacol ester

97%

Synonym(s):

4,4,5,5-Tetramethyl-2-(3-methoxy-2-thienyl)-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C11H17BO3S
CAS Number:
1310384-98-5
Molecular Weight:
240.13
MDL number:
MFCD09837621
UNSPSC Code:
12352103
PubChem Substance ID:
329762904
NACRES:
NA.22

Assay

97%

form

solid

mp

124-128 °C

SMILES string

COc1ccsc1B2OC(C)(C)C(C)(C)O2

InChI

1S/C11H17BO3S/c1-10(2)11(3,4)15-12(14-10)9-8(13-5)6-7-16-9/h6-7H,1-5H3

InChI key

FXKKXDGOIQJEJS-UHFFFAOYSA-N

Application

3-Methoxythiophene-2-boronic acid pinacol ester can be used:
  • As an intermediate in the synthesis of benzothiadiazole derivatives, which are used as building blocks in the preparation of organic semiconductors.
  • As a starting material in the synthesis of imidazo[1,2-a]pyridine derivatives exhibiting bright excited-state intramolecular proton transfer (ESIPT) luminescence property in solid-state.
  • As a starting material in the preparation of polycyclic aromatic triptycenes.

Storage Class Code

13 - Non 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
MKBC0457V
50496BM
MKBC0457

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Synthesis of benzothiadiazole derivatives by applying C--C cross-couplings
Heiskanen JP, et al.
The Journal of Organic Chemistry, 81(4), 1535-1546 (2016)
Development of imidazo [1, 2-a] pyridine derivatives with an intramolecular hydrogen-bonded seven-membered ring exhibiting bright ESIPT luminescence in the solid state
Mutai T, et al.
Organic Letters, 21(7), 2143-2146 (2019)
Polycyclic aromatic triptycenes: oxygen substitution cyclization strategies
VanVeller B, et al.
Journal of the American Chemical Society, 134(17), 7282-7285 (2012)

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