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719013

Sigma-Aldrich

(Piperidinium-1-ylmethyl)trifluoroborate

internal salt

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About This Item

Empirical Formula (Hill Notation):
C6H13BF3N
CAS Number:
1268340-93-7
Molecular Weight:
166.98
MDL number:
MFCD18071160
UNSPSC Code:
12352103
PubChem Substance ID:
329763622
NACRES:
NA.22

form

solid

mp

134-149 °C

SMILES string

F[B-](F)(F)C[NH+]1CCCCC1

InChI

1S/C6H12BF3N/c8-7(9,10)6-11-4-2-1-3-5-11/h1-6H2/q-1/p+1

InChI key

PFMNVTAJBBIDDU-UHFFFAOYSA-O

Application

(Piperidinium-1-ylmethyl)trifluoroborate can be used as a reagent in the palladium-catalyzed Suzuki-cross coupling reaction with aryl and heteroaryl halides/mesylates to prepare methylpiperidinyl derivatives.[1][2]
Organotrifluoroborate involved in Suzuki-Miyaura cross-coupling and cross coupling with mesylated phenol derivatives

Organotrifluoroborates as versatile and stable boronic acid surrogates.

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
MKBC5796

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Reinvestigation of aminomethyltrifluoroborates and their application in Suzuki- Miyaura cross-coupling reactions
Raushel J, et al.
The Journal of Organic Chemistry, 76(8), 2762-2769 (2011)
Cross-coupling of mesylated phenol derivatives with potassium ammonio-and amidomethyltrifluoroborates
Molander GA and Beaumard F
Organic Letters, 13(5), 1242-1245 (2011)

Articles

Potassium Organotrifluoroborates

Bench-stable Potassium Organotrifluoroborates enable diverse C-C bond formation reactions.

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