2,2,2-Trifluorodiazoethane (CF3CHN2) has been proven to be a valuable reagent for the rapid synthesis of various classes of trifluoromethyl-substituted organic molecules in both academic and industrial research. The reagent was prepared first in 1943, but only recently it received a great attention from the scientific community. Protocols for in situ generation, in flow generation, and crystalline analogues of CF3CHN2 were developed during the past decade and have led to an ever-increasing number of publications on the topic. The current review summarizes and comprehensively analyzes all manuscripts in a peer-reviewed literature on 2,2,2-trifluorodiazoethane since its discovery in 1943 until today (as of 19 June 2020). These include contributions mostly overseen by scientific community before. A particular emphasis of this review is to classify the existing reactivity modes of CF3CHN2 and to systematically analyze the corresponding reaction mechanisms in details. At the end of this review, several undeveloped areas for CF3CHN2 are outlined, based on the overseen precedents in the literature.

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943.

Enantiopure aziridines are versatile chiral building blocks that have a high potential for further elaboration to a wide range of chiral nitrogen-containing derivatives. The aziridine ring is not only an important reactive intermediate but is also present in many biologically active
compounds. In the context of an explosion of research in organofluorine chemistry due to the matchless properties of fluorinated molecules,
trifluoromethylated building blocks are privileged scaffolds for library design and drug discovery. Herein, we report the first catalytic asymmetric
synthesis of CF3-substituted aziridines that is remarkable for its simplicity, a low catalyst loading, and very high enantioselectivity.

https://hal.archives-ouvertes.fr/hal-02913343/document

Chiral Brønsted acid-catalyzed diastereo- and enantioselective synthesis of CF3-substituted aziridines

Cu‐Catalysed Three‐Component Reaction of Aryldiazonium Salts with Fluorinated Diazo Reagents and Nitriles: Access to Difluoro‐ and Trifluoromethylated N1‐Aryl‐1,2,4‐triazoles

[371-67-5] C2HF3N2 (MW 110.04)





InChI = InChI=1S/C2HF3N2/c3-2(4,5)1-7-6/h1H



InChIKey = YWUIUNGMQOICND-UHFFFAOYSA-N



(trifluoroethyl carbene source for cyclopropanation; 1,3-dipole reagent for dipolar cycloaddition)



Alternate Names: ethane, 2-diazo-1,1,1-trifluoro-; 1-diazo-2,2,2-trifluoroethane; 2-diazo-1,1,1-trifluoroethane; trifluoromethyl diazomethane; 2,2,2-trifluorodiazoethane



Physical Data: bp 13 °C.



Solubility: sol ether, dichloromethane, toluene.



Form Supplied in: not commercially available.



Preparative Methods: diazotization of 2,2,2-trifluoroethylamine hydrochloride.



Handling, Storage, and Precautions: toxic, explosive, and gaseous at room temperature. Trifluoromethyl diazomethane should be stored in an ethereal solution under anhydrous conditions at low temperature (e.g. −15 °C).

Wen-Jing Xiao

Papers

1,1,1-Trifluorodiazomethane