719013
(Piperidinium-1-ylmethyl)trifluoroborate
internal salt
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About This Item
Empirical Formula (Hill Notation):
C6H13BF3N
CAS Number:
Molecular Weight:
166.98
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352103
MDL number:
Form:
solid
Product Name
(Piperidinium-1-ylmethyl)trifluoroborate, internal salt
InChI
1S/C6H12BF3N/c8-7(9,10)6-11-4-2-1-3-5-11/h1-6H2/q-1/p+1
SMILES string
F[B-](F)(F)C[NH+]1CCCCC1
InChI key
PFMNVTAJBBIDDU-UHFFFAOYSA-O
form
solid
mp
134-149 °C
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.
Organotrifluoroborate involved in Suzuki-Miyaura cross-coupling and cross coupling with mesylated phenol derivatives
Organotrifluoroborates as versatile and stable boronic acid surrogates.
Organotrifluoroborates as versatile and stable boronic acid surrogates.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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
Bench-stable Potassium Organotrifluoroborates enable diverse C-C bond formation reactions.
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