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165336

Sigma-Aldrich

Methylboronic acid

97%

Sinônimo(s):

Methaneboronic acid

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About This Item

Fórmula linear:
CH3B(OH)2
Número CAS:
13061-96-6
Peso molecular:
59.86
Beilstein:
1731087
Número MDL:
MFCD00002105
Código UNSPSC:
12352103
ID de substância PubChem:
24850133
NACRES:
NA.22

Nível de qualidade

100

Ensaio

97%

Formulário

solid

pf

91-94 °C (lit.)

cadeia de caracteres SMILES

CB(O)O

InChI

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

chave InChI

KTMKRRPZPWUYKK-UHFFFAOYSA-N

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Categorias relacionadas

Aplicação

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

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
0000269323
SHBM7877
SHBJ8932
SHBH6335

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Phenethylboronic acid

Sigma-Aldrich

588423

Phenethylboronic acid

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
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)
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)
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
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)
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