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710075

Sigma-Aldrich

(Thiomorpholinium-4-ylmethyl)trifluoroborate

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About This Item

Empirical Formula (Hill Notation):
C5H11BF3NS
CAS Number:
Molecular Weight:
185.02
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

description

internal salt

form

solid

mp

146-156 °C

SMILES string

F[B-](F)(F)C[NH+]1CCSCC1

InChI

1S/C5H10BF3NS/c7-6(8,9)5-10-1-3-11-4-2-10/h1-5H2/q-1/p+1

InChI key

VUNVVPNMYVRSKZ-UHFFFAOYSA-O

Application

Organotrifluoroborate involved in Suzuki-Miyaura cross-coupling reactions and cross coupling with mesylated phenol derivatives

Organotrifluoroborates as versatile and stable boronic acid surrogates

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Gary A Molander et al.
Organic letters, 13(5), 1242-1245 (2011-02-08)
A large array of aryl and heteroaryl mesylates have been successfully employed as electrophiles in a Csp(2)-Csp(3) Suzuki-Miyaura cross-coupling with potassium ammonio- and amidomethyltrifluoroborates to afford the corresponding products in high yields.
Jessica Raushel et al.
The Journal of organic chemistry, 76(8), 2762-2769 (2011-03-17)
A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in

Articles

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

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