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906298

Sigma-Aldrich

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H4BrF3N2
CAS Number:
952143-02-1
Molecular Weight:
265.03
UNSPSC Code:
12352101

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

Related Categories

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.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

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

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Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Naoko Ichiishi et al.
ACS medicinal chemistry letters, 10(1), 56-61 (2019-01-19)
Access to high quality photoaffinity probe molecules is often constrained by synthetic limitations related to diazirine installation. A survey of recently published photoaffinity probe syntheses identified the Suzuki-Miyaura (S-M) coupling reaction, ubiquitous in drug discovery, as being underutilized to incorporate
Formate assay in body fluids: application in methanol poisoning.
A B Makar et al.
Biochemical medicine, 13(2), 117-126 (1975-06-01)

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