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165336

Sigma-Aldrich

Methylboronic acid

97%

Sinonimo/i:

Methaneboronic acid

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About This Item

Formula condensata:
CH3B(OH)2
Numero CAS:
13061-96-6
Peso molecolare:
59.86
Beilstein:
1731087
Numero MDL:
MFCD00002105
Codice UNSPSC:
12352103
ID PubChem:
24850133
NACRES:
NA.22

Livello qualitativo

100

Saggio

97%

Stato

solid

Punto di fusione

91-94 °C (lit.)

Stringa SMILE

CB(O)O

InChI

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

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Categorie correlate

Applicazioni

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
0000269323
0000269323
SHBM7877
0000147043

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Sigma-Aldrich

588423

Phenethylboronic acid

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Talanta, 205, 120067-120067 (2019-08-28)
2,7-Naphthyridine derivatives were developed as fluorophores for the first time to design two fluorescence probes, AND-DNP and ND-DNP, which can be applied for detecting thiophenol in aqueous media. Comparing with ND-DNP, AND-DNP showed more favorable properties such as lower background
Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals
Verdelet, T.; et al.
Tetrahedron, 67, 8757-8762 (2011)
Aryl- or Alkylation of Diaryl Disulfides Using Organoboronic Acids and a Copper Catalyst
Taniguchi N
Synlett, 9, 1351-1354 (2006)
A comparative study of ethylene polymerization by bis(aminotropone) Ti catalysts
Goldani, M. T.; et al.
Polym. Bull., 68, 755-773 (2012)
Ling Zhou et al.
Journal of the American Chemical Society, 132(44), 15474-15476 (2010-10-16)
A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of γ-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of
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