952143-02-1

Basic information

• Product Name: 3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine
• CAS NO: 952143-02-1
• Molecular Weight: 265.032
• Mol File: 952143-02-1.mol

Chemical Properties

• CAS DataBase Reference: 3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine(952143-02-1)
• EPA Substance Registry System: 3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine(952143-02-1)

Safety Data

• Hazardous Substances Data: 952143-02-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Biology and Drug Discovery Research:
3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine is used as a building block for the development of photoaffinity probes (PAPs) for various applications in chemical biology and drug discovery research. These applications include protein profiling, covalent inhibitors, protein-protein interactions and complexes, and target engagement, identification, or validation studies.
Used in Photoaffinity Labeling (PAL):
3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine is used as a photoactivable group in photoaffinity labeling (PAL) techniques. PAL is a method of growing interest in chemical biology and drug discovery research, as it allows for the study of protein targets and their interactions with high spatial and temporal resolution.
Used in Suzuki-Miyaura (S-M) Cross-Coupling:
3-(4-bromophenyl)-3-(trifluoromethyl)-3H-diazirine is used in Suzuki-Miyaura (S-M) cross-coupling reactions, which are efficient and scalable methods for the synthesis of various organic compounds. The diazirine-tolerant S-M coupling conditions developed by Ichiishi et al. allow for the installation of this diazirine group with minimal perturbation, facilitating the synthesis of complex molecules for research purposes.

Upstream product

• 16184-89-7 4'-bromo-2,2,2-trifluoroacetophenone 
• 106-37-6 1.4-dibromobenzene 
• 952142-96-0 1-(4-bromophenyl)-2,2,2-trifluoroethanone O-(p-tolylsulfonyl)oxime 
• 292145-64-3 1-(4-bromophenyl)-2,2,2-trifluoroethanone oxime 
• 952142-99-3 3-(4-bromophenyl)-3-(trifluoromethyl)diaziridine 

Relevant articles and documents

Photochemical Cyclopropenation of Alkynes with Diazirines as Carbene Precursors in Continuous Flow

An efficient synthesis of 3-trifluoromethyl-3-aryl-cyclopropenes via the cyclopropenation reaction of alkynes with photolytically generated carbenes from diazirine compounds is described. This reaction is performed in continuous flow using readily available LEDs under mild reaction conditions. This new and efficient method describes the synthesis of 25 examples of 3-trifluoromethyl-3-aryl-cyclopropenes with yields up to 97%, achieved in continuous flow with a 5 min residence time. Control experiments highlighted that diazirines are more efficient than diazo compounds for this transformation.

Convenient synthesis of a [1-14C]diazirinylbenzoic acid as a photoaffinity label for binding studies of V-ATPase inhibitors

Diazirine-tagged systems are considered reliable compounds for photoaffinity labeling (PAL) in biochemical studies as they enable investigation and understanding of biological mechanisms through covalent bonding to the target and subsequent detection. 14C-labeled 4-(3-trifluoromethyl-3H- diazirin-3-yl)benzoic acid (11) was prepared by a lithium-bromide exchange on the bis-silylated 4-bromophenyldiaziridine 19 with subsequent transformations with electrophiles as key steps of the synthesis. Using 14CO 2, which was generated from rather inexpensive Ba14CO 3, the desired diaziridinylbenzoic acid 21 was obtained in 78% yield based on the employed radioactive material. Oxidation under mild conditions then yielded diazirine 11 in a 100 mg scale. This versatile photoaffinity label was selectively attached to the tetrahydropyrane ring of bafilomycin A1 (2) and concanamycin A-derived 3, which both specifically inhibit the V-ATPases. Inhibition assays were performed and revealed that the inhibitory capacities of the labeled derivatives are suitable for PAL studies on this important group of enzymes to elucidate the as yet unknown binding sites. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.