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906298

Sigma-Aldrich

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

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C8H4BrF3N2
Numero CAS:
Peso molecolare:
265.03
Numero MDL:
Codice UNSPSC:
12352101
NACRES:
NA.22

Saggio

≥95%

Stato

liquid

Impiego in reazioni chimiche

reagent type: cross-linking reagent

Temperatura di conservazione

2-8°C

Stringa SMILE

BrC1=CC=C(C2(N=N2)C(F)(F)F)C=C1

InChI

1S/C8H4BrF3N2/c9-6-3-1-5(2-4-6)7(13-14-7)8(10,11)12/h1-4H
YBEXZCGWGWNLQQ-UHFFFAOYSA-N

Applicazioni

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)

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


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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
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A B Makar et al.
Biochemical medicine, 13(2), 117-126 (1975-06-01)

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