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78181

Phenylboronic acid

purum, ≥97.0% (HPLC)

Synonyma:

Benzeneboronic acid, Dihydroxyphenylborane, NSC 66487, Phenyl-boric acid, Phenylboric acid, Phenyldihydroxyborane

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Velikost baleníSkladová položkaDostupnostCena
1 g
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1 930,00 Kč
10 g
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2 040,00 Kč
50 g
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7 500,00 Kč

O této položce

Lineární vzorec:
C6H5B(OH)2
Číslo CAS:
Molekulová hmotnost:
121.93
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
202-701-9
Beilstein/REAXYS Number:
970972
MDL number:

1 930,00 Kč


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grade

purum

Quality Segment

assay

≥97.0% (HPLC)

form

crystals

mp

216-219 °C (lit.), 218-222 °C

SMILES string

OB(O)c1ccccc1

InChI

1S/C6H7BO2/c8-7(9)6-4-2-1-3-5-6/h1-5,8-9H

InChI key

HXITXNWTGFUOAU-UHFFFAOYSA-N

General description

Phenylboronic acid is a highly stable receptor ligand used in cross-coupling reactions and drug delivery.

Phenylboronic acid (PBA) is an organoboronic acid. It behaves as a molecular receptor that can attach to compounds containing cis-diol group.[1] Microwave-assisted Suzuki coupling of aryl chlorides with phenylboronic acid in the presence of Pd/C (catalyst) and water (solvent) has been described.[2] Palladium-catalyzed cross-coupling reaction of phenylboronicacid with haloarenes to afford biaryls has been reported.

Application

Phenylboronic acid may be employed in the following reactions:
  • Rhodium-catalyzed intramolecular amination.[3]
  • Pd-catalyzed direct arylation.
  • Mizoroki-Heck and Suzuki-Miyaura coupling reactions catalyzed by palladium nanoparticles.
  • Palladium-catalyzed stereoselective Heck-type reaction.
  • Highly effective Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water.

Phenylboronic acid may be employed as reagent in the preparation of:
  • Ni(II) pincer complex and Pd(II) pyridoxal hydrazone metallacycles as catalysts for the Suzuki-Miyaura cross-coupling reactions.
  • N-type polymers for all-polymer solar cells.[4]
  • Novel series of potent and selective mTOR kinase inhibitors.
  • Inhibitors of lactate dehydrogenase against cancer cell proliferation.[5]

Other Notes

Contains varying amounts of phenylboronic anhydride

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Tato položka
P20009524018647098
assay

≥97.0% (HPLC)

assay

95%

assay

90%

assay

97%

mp

216-219 °C (lit.), 218-222 °C

mp

216-219 °C (lit.)

mp

>230 °C (lit.)

mp

27-31 °C (lit.)

form

crystals

form

crystals

form

solid

form

solid

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

grade

purum

grade

-

grade

-

grade

-


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pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Skladovací třída

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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Peng-Cheng Chen et al.
Langmuir : the ACS journal of surfaces and colloids, 27(20), 12597-12605 (2011-09-09)
Phenylboronic acid (PBA)-functionalized materials have attracted considerable attention because of their potential applications in many fields. In this paper, we report a PBA-segregated honeycomb-patterned porous film (HPPF) for glucose sensing. Polystyrene-block-poly(acrylic acid-co-acrylamidophenylboronic acid) with different contents of PBA pendants was
Synthesis of polyfunctional glycerol esters: lipase-catalyzed esterification of glycerol with diesters.
Villeneuve P, et al.
Journal of the American Oil Chemists' Society, 75(11), 1545-1549 (1998)
Phenylboronic-acid-based functional chemical materials for fluorescence imaging and tumor therapy
Li S, et al.
ACS Omega, 7, 2520-2532 (2022)



Globální číslo obchodní položky

Skladová položkaGTIN
PH015129-100MG04061831271751
78181-1G04061826140017
78181-50G04061832943336
78181-10G04061832943312

Questions

1–2 of 2 Questions  
  1. 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/418/501/product-dating-information-06-25-mk.pdf

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  2. 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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