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720747

Sigma-Aldrich

Potassium (2Z)-2-buten-2-yltrifluoroborate

≥95%

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About This Item

Empirical Formula (Hill Notation):
C4H7BF3K
CAS Number:
1134643-88-1
Molecular Weight:
162.00
MDL number:
MFCD16621473
UNSPSC Code:
12352103
PubChem Substance ID:
329763746
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

solid

mp

147-152 °C

storage temp.

2-8°C

SMILES string

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

InChI

1S/C4H7BF3.K/c1-3-4(2)5(6,7)8;/h3H,1-2H3;/q-1;+1/b4-3+;

InChI key

IFJZXYDBLMMRCO-BJILWQEISA-N

Application

Potassium (2Z)-2-buten-2-yltrifluoroborate can be used as a substrate:
  • In the asymmetric alkenylation of imines/aldimines using a rhodium based catalyst.
  • In the Rh(I)-catalyzed allylic amines synthesis by reacting with N-tert-butanesulfinyl aldimines.
  • In the ytterbium triflate catalyzed multicomponent synthesis of β-unsaturated α-amino esters.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG3727
MKBR8238V
MKBQ2221V
MKBP5184V
MKBD3764

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Three-component reaction for the synthesis of diverse β-unsaturated α-amino esters
Stefani HA, et al.
Tetrahedron, 70(20), 3243-3248 (2014)
Highly enantioselective Rh-catalyzed alkenylation of imines: synthesis of chiral allylic amines via asymmetric addition of potassium alkenyltrifluoroborates to N-Tosyl imines
Gopula B, et al.
Organic Letters, 16(2), 632-635 (2014)
Enantioselective Alkenylation of Aldimines Catalyzed by a Rhodium-Diene Complex
Cui Z, et al.
Organic Letters, 16(3), 1016-1019 (2014)
Asymmetric synthesis of α-branched allylic amines by the Rh (I)-catalyzed addition of alkenyltrifluoroborates to N-tert-butanesulfinyl aldimines
Brak K and Ellman JA
Journal of the American Chemical Society, 131(11), 3850-3851 (2009)

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