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Merck

165336

Sigma-Aldrich

Methylborsäure

97%

Synonym(e):

Methanboronsäure

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CHF 49.60
5 G
CHF 106.00

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1 G
CHF 49.60
5 G
CHF 106.00

About This Item

Lineare Formel:
CH3B(OH)2
CAS-Nummer:
Molekulargewicht:
59.86
Beilstein:
1731087
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.22

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Qualitätsniveau

Assay

97%

Form

solid

mp (Schmelzpunkt)

91-94 °C (lit.)

SMILES String

CB(O)O

InChI

1S/CH5BO2/c1-2(3)4/h3-4H,1H3

InChIKey

KTMKRRPZPWUYKK-UHFFFAOYSA-N

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Anwendung

Methylboronic acid can be used as a reagent:
  • In the palladium-catalyzed Stille and Suzuki-Miyaura cross-couplings.[1][2]
  • In the microwave-heated heterogeneous palladium (Pd)-catalytized reactions.[3]
  • In ruthenium (Ru)-catalyzed silylation reactions[4]
  • To prepare bis(aminotropone) titanium (Ti) catalysts for ethylene polymerizations.[5]
  • In the enantioselective asymmetric bromoaminocyclization and bromoaminocyclization using amino-thiocarbamate catalysts.[6][7]
  • To prepare common building blocks for pharmaceuticals and agrochemicals.[8]
  • To prepare chrysin analogs by Suzuki-Miyaura coupling reactions.[9]
  • To prepare casein kinase I inhibitors.[10]
  • In the divergent C-H functionalizations directed by sulfonamide pharmacophores in drug discovery.[2]
  • In the synthesis of unsymmetrical monosulfides from disulfides via copper-catalyzed coupling with boronic acids.[11]
  • In a palladium-catalyzed coupling with enol tosylates.[12]
  • For derivatizing many carbohydrates and biologically active compounds for GLC analysis.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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1 of 1

Hui-Xiong Dai et al.
Journal of the American Chemical Society, 133(18), 7222-7228 (2011-04-15)
Modern drug discovery is contingent on identifying lead compounds and rapidly synthesizing analogues. The use of a common pharmacophore to direct multiple and divergent C-H functionalizations of lead compounds is a particularly attractive approach. Herein, we demonstrate the viability of
Ling Zhou et al.
Journal of the American Chemical Society, 133(24), 9164-9167 (2011-05-05)
A facile and efficient enantioselective bromoaminocyclization of unsaturated sulfonamides has been developed using an amino-thiocarbamate catalyst. A range of enantioenriched pyrrolidines were prepared with up to 99% yield and 99% ee. The corresponding lactams could be obtained through oxidation of
Ruthenium-catalyzed C-H silylation of methylboronic acid using a removable a-directing modifier on the boron atom
Ihara, H.; Ueda, A.; Suginome, M.
Chemistry Letters (Jpn), 40, 916-918 (2011)
Selective heating of Pd-modified ordered mesoporous carbon CMK-3 by microwave irradiation
Inagaki, S.; et al.
Bulletin of the Chemical Society of Japan, 84, 1136-1143 (2011)
Chemical Development of the Casein Kinase I - Epsilon Inhibitor: 3-(3-Fluorophenyl)sulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic Acid Amide
Huang, B-G.; et al.
Organic Process Research & Development, 15, 1040-1045 (2011)

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/449/386/product-dating-information-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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