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436836

Sigma-Aldrich

2-Thienylboronic acid

≥95.0%

Synonym(s):

2-Thienylboric acid, 2-Thienylboronic acid, Thien-5-ylboronic acid, Thiophene-2-boronic acid

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About This Item

Empirical Formula (Hill Notation):
C4H5BO2S
CAS Number:
6165-68-0
Molecular Weight:
127.96
Beilstein:
112375
MDL number:
MFCD00151850
UNSPSC Code:
12352103
PubChem Substance ID:
24867305
NACRES:
NA.22
Pricing and availability is not currently available.

Assay

≥95.0%

form

solid

mp

138-140 °C (lit.)

storage temp.

2-8°C

SMILES string

OB(O)c1cccs1

InChI

1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H

InChI key

ARYHTUPFQTUBBG-UHFFFAOYSA-N

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Application

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura cross-couplings[1]
  • Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide[2]
  • Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer[3]
  • Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters[4]
  • Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions[5]
  • Copper-catalyzed nitration reactions[6]
  • Geometry relaxation-induced Large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes[7]

Reagent used in Preparation of
  • Photophysical properties of oxygen-containing polycyclic aromatic triptycenes[8]
  • Donor unit for donor-acceptor-type polymers via N-alkylation, Suzuki coupling, and bromination[9]
  • Aminopyridine-based inhibitors of mitotic kinase Nek2 with potential antipoliferative effects in cancer tumors[10]

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000363980
0000363980
0000262205
0000209100
MKCP6694

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Chain-growth catalyst transfer polycondensation of a conjugated alternating copolymer
Ono, R. J.; Bielawski, C. W.
Polymeric Materials: Science and Engineering Preprints (2012)
Synthesis of a novel donor unit for D-A-type polymers, 2,7-di(5-bromothiophen-2-yl)-10-hexadecyl-phenoxazine
Li, L.; et al.
Advanced Materials Research, 418-420 (2012)
Synthesis of a novel fluorene derivative for polyfluorenes. 7,7'-Di(5-bromothiophen-2-yl)-9,9,9',9'-tetraoctyl-2,2'-bifluorene
Li, L.; et al.
Advanced Materials Research, 418-420 (2012)
Guo-Ping Lu et al.
The Journal of organic chemistry, 77(8), 3700-3703 (2012-04-07)
The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and
Yinghui Chen et al.
The Journal of organic chemistry, 77(5), 2192-2206 (2012-02-10)
2-Thienyl and 2,6-bisthienyl BODIPY derivatives (BS-SS and BS-DS) were prepared that show intense absorption (ε = 65000 M(-1) cm(-1) at 507 nm) and a large Stokes shift (96 nm) vs the small Stokes shift of typical BODIPY (<15 nm). Control
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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