906298
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:
Molecular Weight:
265.03
MDL number:
UNSPSC Code:
12352101
NACRES:
NA.22
form
liquid
InChI
1S/C8H4BrF3N2/c9-6-3-1-5(2-4-6)7(13-14-7)8(10,11)12/h1-4H
InChI key
YBEXZCGWGWNLQQ-UHFFFAOYSA-N
SMILES string
BrC1=CC=C(C2(N=N2)C(F)(F)F)C=C1
assay
≥95%
reaction suitability
reagent type: cross-linking reagent
storage temp.
2-8°C
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)
Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_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
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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