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Trifluoromethyl phenyl diazirine amine

Trifluoromethylphenyldiazirines are one type of the most effective diazirines with generally high photoreaction reaction yield by UV irradiation (~350 nm). Diazirines are known for their ability to undergo photochemical reactions when exposed to ultraviolet (UV) light, specifically by forming highly reactive carbene intermediates that react with nearby molecules. The phenylcarbenes generated by the UV irradiation of trifluoromethylphenyldiazirines have much higher reactivity than nitrenes (generated by phenylazides). Phenylcarbene is incactivated by water when neighboring target molecules are absent, and thus does not lead to non-specific crosslinking. This property makes diazirines useful for studying protein-protein, protein-nucleic acid interactions, ligand-receptor binding, and other biomolecular interactions. It's important to note that diazirines are highly reactive and can be challenging to handle due to their instability.

References

View all 36 references: Citation Explorer
Comprehensive computational study on reaction mechanism of N-Nitroso dimethyl amine formation from substituted hydrazine derivatives during ozonation.
Authors: Sulay, Rehin and Mathew, Jintumol and Krishnan, Anandhu and Thomas, Dr Vibin Ipe
Journal: Heliyon (2023): e14511
Transcriptome-Wide Studies of RNA-Targeted Small Molecules Provide a Simple and Selective r(CUG)exp Degrader in Myotonic Dystrophy.
Authors: Gibaut, Quentin M R and Bush, Jessica A and Tong, Yuquan and Baisden, Jared T and Taghavi, Amirhossein and Olafson, Hailey and Yao, Xiyuan and Childs-Disney, Jessica L and Wang, Eric T and Disney, Matthew D
Journal: ACS central science (2023): 1342-1353
Strategy for Conjugating Oligopeptides to Mesoporous Silica Nanoparticles Using Diazirine-Based Heterobifunctional Linkers.
Authors: Khan, Md Arif and Ghanim, Ramy W and Kiser, Maelyn R and Moradipour, Mahsa and Rogers, Dennis T and Littleton, John M and Bradley, Luke H and Lynn, Bert C and Rankin, Stephen E and Knutson, Barbara L
Journal: Nanomaterials (Basel, Switzerland) (2022)
Fabrication of PAMAM antimicrobial monolayer via UV induced grafting on the surface of polyethylene terephthalate.
Authors: Zhang, Haobo and Wang, Weihan and Wei, Lilong and Wu, Dezhen and Cheng, Jue and Gao, Feng
Journal: Colloids and surfaces. B, Biointerfaces (2021): 111601
Dirhodium-Catalyzed Enantioselective B-H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes.
Authors: Zhao, Yu-Tao and Su, Yu-Xuan and Li, Xiao-Yu and Yang, Liang-Liang and Huang, Ming-Yao and Zhu, Shou-Fei
Journal: Angewandte Chemie (International ed. in English) (2021): 24214-24219
Page updated on April 15, 2025

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Catalog Number39009
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Physical properties

Molecular weight

251.64

Solvent

DMSO

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C); Minimize light exposure

CAS

1258874-29-1
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