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750271

Sigma-Aldrich

Potassium trans-1-propenyltrifluoroborate

97%

Synonym(s):

Potassium (E)-trifluoro(1-propenyl)borate

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About This Item

Empirical Formula (Hill Notation):
C3H5BF3K
CAS Number:
804565-39-7
Molecular Weight:
147.98
MDL number:
MFCD09992882
UNSPSC Code:
12352103
PubChem Substance ID:
329766067
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

81-85 °C

SMILES string

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

InChI

1S/C3H5BF3.K/c1-2-3-4(5,6)7;/h2-3H,1H3;/q-1;+1/b3-2+;

InChI key

RLDWVFWDURMTAV-SQQVDAMQSA-N

Application

Potassium trans-1-propenyltrifluoroborate can be used:
  • As a substrate in the cross-coupling reactions with 2-(chloromethyl)-2,1-borazaronaphthalenes to yield allyl borazaronaphthalenes using a palladium catalyst.
  • In the synthesis of anethole dithiolethione-NH2 (ADT-NH2), which in turn is used to prepare a drug-H2S delivery system.
  • To prepare methyl (E)-2,2-dimethyl-5-(propen-1-yl)-4H-benzo[d][1,3]dioxine-7-carboxylate, a key intermediate for the synthesis of the alkaloid ampullosine.

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
0000237112
0000226157
0000230307
0000230791
MKCL0609

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First total synthesis of ampullosine, a unique isoquinoline alkaloid isolated from Sepedonium ampullosporum, and of the related permethylampullosine
Vargas DF, et al.
Royal Society of Chemistry Advances, 9(57), 33096-33106 (2019)
Synthesis of amino-ADT provides access to hydrolytically stable amide-coupled hydrogen sulfide releasing drug targets
Hammers MD, et al.
Synlett, 27(09), 1349-1353 (2016)
Accessing 2-(Hetero) arylmethyl-,-allyl-, and-propargyl-2, 1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2, 1-borazaronaphthalenes
Molander GA, et al.
Organic Letters, 16(22), 6024-6027 (2014)

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