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906298 Sigma-Aldrich

3-(4-Bromophenyl)-3-(trifluoromethyl)-3H-diazirine

Synonym: Probe building block for photoaffinity labeling, Suzuki-Miyaura-compatible multifunctional photo probe building block, Trifluoromethyl diazirine aryl bromide

  • CAS Number 952143-02-1

  • Empirical Formula (Hill Notation) C8H4BrF3N2

  • Molecular Weight 265.03

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Properties

Related Categories Bifunctional Linkers, Chemical Biology, Chemical Synthesis, Linkers and Crosslinkers
assay   ≥95%
form   liquid
reaction suitability   reagent type: cross-linking reagent
storage temp.   2-8°C
SMILES string   BrC1=CC=C(C2(N=N2)C(F)(F)F)C=C1

Description

Application

3-(4-Bromophenyl)-3-(trifluoromethyl)-3H-diazirine is a Suzuki-Miyaura (S−M)-compatible building block tailored for the design of photoaffinity probes (PAPs). Photoaffinity labeling (PAL) is of growing interest in chemical biology and drug discovery research for use in protein profiling; covalent inhibitors; protein-protein interactions and complexes; and target engagement, identification, or validation studies. Diazirines are desirable photoactivable groups for chemical probes; however, their installation is not always straightforward. In response, diazirine-tolerant S-M coupling conditions were developed by Ichiishi, et al, using 3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine and shown to be efficient and scalable with minimal perturbation of the diazirine.

Other Notes

Reducing Limitation in Probe Design: The Development of a Diazirine-Compatible Suzuki-Miyaura Cross Coupling Reaction

Safety & Documentation

Safety Information

WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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