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904848

Sigma-Aldrich

2-Chloro-1,3-bis(2,6-diisopropylphenyl)imidazolium chloride

≥95%

Synonym(s):

1,3-Bis(2,6-di-i-propylphenyl)-2-chloroimidazolium chloride, Chloroimidazolium chloride

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About This Item

Empirical Formula (Hill Notation):
C27H36Cl2N2
CAS Number:
1228185-09-8
Molecular Weight:
459.49
MDL number:
MFCD23703069
UNSPSC Code:
12352101
NACRES:
NA.22

Assay

≥95%

form

powder

functional group

chloro

InChI

1S/C27H36ClN2.ClH/c1-17(2)21-11-9-12-22(18(3)4)25(21)29-15-16-30(27(29)28)26-23(19(5)6)13-10-14-24(26)20(7)8;/h9-20H,1-8H3;1H/q+1;/p-1

InChI key

JDMACANGISWEGX-UHFFFAOYSA-M

Application

This chloroimidazolium chloride is used in the deoxyfluorination of phenols. Recently, the Ritter lab used it in conjunction with 902314 and 906794 to incorporate the [18F]fluoride radiolabel site specifically into polypeptides for use with positron emission tomography (PET) imaging in the study of various biological applications.

Automate your fluorination reactions with Synple Automated Synthesis Platform (SYNPLE-SC002)

Other Notes

Site-specific deoxyfluorination of small peptides with [18F]fluoride

HDAC6 Brain Mapping with [18F]Bavarostat Enabled by a Ru-Mediated Deoxyfluorination

18F-Deoxyfluorination of Phenols via Ru p-Complexes

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
MKCT1190
MKCJ8905
MKCT3587

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1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride 95%

Sigma-Aldrich

656631

1,3-Bis(2,4,6-trimethylphenyl)imidazolinium chloride

Robert J Gilliard et al.
Chemical communications (Cambridge, England), 53(91), 12325-12328 (2017-11-03)
The reaction of the chloroimidazolium chloride salt, [NHC-Cl][Cl], NHC = C{N(2,6-iPr2C6H3)CH}2 (1) with two equivalents of sodium phosphaethynolate, Na[OCP]·(dioxane)2.5, results in the formation of NHC-{cyclo-(CO)-P2-C(O)} (2) and NHC-P2-C(O)-NHC (3). Notably, in the presence of free NHC ligand, compound 2 converts
M Hassan Beyzavi et al.
ACS central science, 3(9), 944-948 (2017-10-06)
The deficiency of robust and practical methods for 18F-radiofluorination is a bottleneck for positron emission tomography (PET) tracer development. Here, we report the first transition-metal-assisted 18F-deoxyfluorination of phenols. The transformation benefits from readily available phenols as starting materials, tolerance of
Daniel Mendoza-Espinosa et al.
Journal of the American Chemical Society, 132(21), 7264-7265 (2010-05-07)
Using the nucleophilicity of NHCs and aNHCs, as well as the leaving group ability of the former, the carbon-carbon double bond of imidazol-2-ylidenes can be readily mono- and difunctionalized. These results provide also a new light on the formation of
Teppei Fujimoto et al.
Organic process research & development, 18(8), 1041-1044 (2014-09-02)
We report a practical synthesis method of the reagent PhenoFluor on decagram scale, provide a new formulation of PhenoFluor as a toluene solution, which should decrease challenges associated with the moisture sensitivity of the reagent, and expand the substrate scope
Jisu Back et al.
Journal of the American Chemical Society, 139(43), 15300-15303 (2017-10-19)
Notwithstanding the notable progress in the synthesis of N-heterocyclic carbene-stabilized radicals, aminyl radicals, supported by NHCs or otherwise, have been scarcely studied due to synthetic challenges. Triazenyl radical is a particular form of aminyl radical that contains three adjacent nitrogen
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