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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
MKCJ8905

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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
Teppei Fujimoto et al.
Organic letters, 17(3), 544-547 (2015-01-27)
A practical deoxyfluorination with novel deoxyfluorinating reagent PhenoFluorMix, a mixture of N,N'-1,3-bis(2,6-diisopropylphenyl)chloroimidazolium chloride and CsF, is presented. PhenoFluorMix overcomes the challenges associated with hydrolysis of PhenoFluor. PhenoFluorMix does not hydrolyze, is readily available on decagram scale, and is storable in
Nathaniel W Goldberg et al.
Organic letters, 18(23), 6102-6104 (2016-12-10)
A practical, high-yielding method for the deoxyfluorination of alcohols is presented using AlkylFluor, a novel salt analogue of PhenoFluor. AlkylFluor is readily prepared on multigram scale and is stable to long-term storage in air and exposure to water. The practicality
Corrigendum: Concerted nucleophilic aromatic substitution with 19F- and 18F.
Constanze N Neumann et al.
Nature, 538(7624), 274-274 (2016-08-04)
Martin G Strebl et al.
ACS central science, 3(9), 1006-1014 (2017-10-06)
Histone deacetylase 6 (HDAC6) function and dysregulation have been implicated in the etiology of certain cancers and more recently in central nervous system (CNS) disorders including Rett syndrome, Alzheimer's and Parkinson's diseases, and major depressive disorder. HDAC6-selective inhibitors have therapeutic
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