73899-14-6

Basic information

• Product Name: 3-Phenyl-3-(trifluoroMethyl)diazirine
• Synonyms: 3-Phenyl-3-(trifluoroMethyl)diazirine;3-Phenyl-3-(trifluoroMethyl)-3H-diazirine;3H-Diazirine, 3-phenyl-3-(trifluoroMethyl)-;3-Phenyl-3-(trifluoromethyl)-3H-diazirine
• CAS NO: 73899-14-6
• Molecular Formula: C₈H₅F₃N₂
• Molecular Weight: 186
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Photoaffinity Labels
• Mol File: 73899-14-6.mol

Chemical Properties

• Boiling Point: 176.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• Refractive Index: 1.4380 to 1.4420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-Phenyl-3-(trifluoroMethyl)diazirine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-3-(trifluoroMethyl)diazirine(73899-14-6)
• EPA Substance Registry System: 3-Phenyl-3-(trifluoroMethyl)diazirine(73899-14-6)

Safety Data

• Hazardous Substances Data: 73899-14-6(Hazardous Substances Data)

Usage

Uses

Used in Biopolymer Research:
3-Phenyl-3-(trifluoroMethyl)diazirine is used as a photophore in photoaffinity labelling for probing receptor-ligand interfaces and other biopolymer research. Its high reactivity and sensitivity to light allow it to form covalent bonds with target molecules upon exposure to ultraviolet light, enabling researchers to study the structure, function, and interactions of biopolymers in detail.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Phenyl-3-(trifluoroMethyl)diazirine is used as a key intermediate in the synthesis of various drug molecules. Its unique photochemical properties make it a valuable building block for the development of new drugs with novel mechanisms of action and improved therapeutic profiles.
Used in Chemical Synthesis:
3-Phenyl-3-(trifluoroMethyl)diazirine is also used in chemical synthesis as a versatile reagent for the preparation of a wide range of organic compounds. Its high reactivity and ability to form stable covalent bonds with various substrates make it a useful tool for the synthesis of complex organic molecules, including natural products, pharmaceuticals, and other specialty chemicals.

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Relevant articles and documents

Photodecarboxylative Amination of Redox-Active Esters with Diazirines

Diazirines have been recently demonstrated to serve as electrophilic amination reagents that afford diaziridines, versatile heterocycles that are readily transformed into amines, hydrazines, and nitrogen-containing heterocycles. Here, we report the photodecarboxylative amination of redox-active esters with diazirines using inexpensive photoactivators under mild conditions with an enhanced scope for primary substrates. The stability of diazirines to blue light is demonstrated, paving the way for further research into other photochemical amination methods with these unique heterocycles.

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.

Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents

The ubiquity of nitrogen-containing small molecules in medicine necessitates the continued search for improved methods for C-N bond formation. Electrophilic amination often requires a disparate toolkit of reagents whose selection depends on the specific structure and functionality of the substrate to be aminated. Further, many of these reagents are challenging to handle, engage in undesired side reactions, and function only within a narrow scope. Here we report the use of diazirines as practical reagents for the decarboxylative amination of simple and complex redox-active esters. The diaziridines thus produced are readily diversifiable to amines, hydrazines, and nitrogen-containing heterocycles in one step. The reaction has also been applied in fluorous phase synthesis with a perfluorinated diazirine.

PROCESSES AND COMPOUNDS FOR THE DECARBOXYLATIVE AMINATION OF REDOX-ACTIVE ESTERS WITH DIAZIRINES

The invention described herein relates generally to processes for the synthesis of amine-containing organic compounds. More specifically, described herein relates to processes for the decarboxylative amination of redox-active esters with diazirines and the products formed thereof. Compounds for use in the above processes are also described.

Alternative one-pot synthesis of (trifluoromethyl)phenyldiazirines from tosyloxime derivatives: Application for new synthesis of optically pure diazirinylphenylalanines for photoaffinity labeling

Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.

COSMETIC USE OF AND COSMETIC COMPOUND CONTAINING PHOTOREACTIVE COMPOUND, PHOTOREACTIVE POLYAMINE AND POLYAMINE SHEET

A use of a polyamine sheet usable for cosmetic purposes is disclosed. A photoreactive polyamine utilized for the creation of this polyamine sheet, and a photoreactive compound that comprises a raw material for this photoreactive polyamine is also disclosed as well as their use for cosmetic purposes and cosmetic compounds containing the same. A photoreactive compound having a diazirine group as a photoreactive group, a photoreactive polyamine compound created from this photoreactive compound and polyamine, a polyamine sheet utilizing this photoreactive polyamine compound, and production methods thereof are disclosed along with their cosmetic uses and cosmetic compounds containing the same.