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655228

Sigma-Aldrich

Potassium vinyltrifluoroborate

95%

Sinonimo/i:

Potassium (ethenyl)trifluoroborate

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About This Item

Formula condensata:
CH2=CHBF3K
Numero CAS:
13682-77-4
Peso molecolare:
133.95
Numero MDL:
MFCD02093335
Codice UNSPSC:
12352103
ID PubChem:
24884089
NACRES:
NA.22

Livello qualitativo

100

Saggio

95%

Stato

solid

Stringa SMILE

[K+].F[B-](F)(F)C=C

InChI

1S/C2H3BF3.K/c1-2-3(4,5)6;/h2H,1H2;/q-1;+1
ZCUMGICZWDOJEM-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

Potassium vinyltrifluoroborate is a versatile organometallic reagent used as a vinylating agent in the presence of palladium catalysts.

Potassium vinyltrifluoroborate is an air- and water-stable potassium organotrifluoroborate that can be utilized in coupling reactions under relatively mild conditions.

Applicazioni

Organotrifluoroborate involved in:
  • Suzuki Miyaura cross-coupling reactions and polymerization reactions
  • Synthesis of photonic crystals
  • Synthesis of sensitizers for dye-sensitized solar cells
  • Mannich / diastereoselective hydroamination reaction sequence

Organotrifluoroborates as versatile and stable boronic acid surrogates.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2

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

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
SHBN1388
SHBL4557
SHBK3923
SHBH9664
SHBG2993V

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Sigma-Aldrich

750271

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The suzuki-heck polymerization as a tool for the straightforward obtainment of poly (fluorenylene-vinylene) sensitizers for dye-sensitized solar cells.
Grisorio R, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49(4), 842-847 (2011)
Suzuki- Miyaura cross-coupling reactions of potassium vinyltrifluoroborate with aryl and heteroaryl electrophiles.
Molander GA and Brown AR
The Journal of Organic Chemistry, 71(26), 9681-9686 (2006)
New poly (phenylenevinylene)-methyl methacrylate-based photonic crystals.
Achelle S, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 48(12), 2659-2665 (2010)
Xuejuan Ma et al.
Journal of hazardous materials, 355, 65-73 (2018-05-19)
The degradation of organophosphorous nerve agents is of primary concern due to the severe toxicity of these agents. Based on the active center of organophosphorus hydrolase (OPH), a bimetallic nuclear ligand, (5-vinyl-1,3-phenylene)bis(di(1H-imidazol-2-yl) methanol) (VPIM), was designed and synthesized, which contains
Potassium organotrifluoroborates: new perspectives in organic synthesis.
Sylvain Darses et al.
Chemical reviews, 108(1), 288-325 (2007-12-22)

Articoli

Potassium Trifluoroborate Salts

Potassium trifluoroborates are a special class of organoboron reagents that offer several advantages over the corresponding boronic acids and esters in that they are moisture- and air-stable, and are remarkably compliant with strong oxidative conditions.

Potassium Organotrifluoroborates

These bench stable Potassium Organotrifluoroborates are useful for Suzuki-Miyaura cross-coupling reactions and have also been used for a variety of other C-C bond forming reactions. Importantly, these reagents are compatible with a wide range of functional groups and are stable to many commonly used and harsh reaction conditions.

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