61881-19-4

Basic information

• Product Name: 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride
• Synonyms: 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride;2,2,2-Trifluoro-N-phenylethanimidoyl chloride;N-Phenyltrifluoroacetimidoyl chloride;2,2,2-Trifluoro-N-phenylacetimidoyl Chloride
• CAS NO: 61881-19-4
• Molecular Formula: C₈H₅ClF₃N
• Molecular Weight: 207.58
• Product Categories: Fluorinated Building Blocks;Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds;Synthetic Organic Chemistry
• Mol File: 61881-19-4.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 53 °C / 10mmHg
• Flash Point: 60℃
• Appearance: /
• Density: 1.28
• Vapor Pressure: 1.544mmHg at 25°C
• Refractive Index: 1.4750-1.4800
• Storage Temp.: 0-10°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -1.60±0.50(Predicted)
• CAS DataBase Reference: 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride(61881-19-4)
• EPA Substance Registry System: 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride(61881-19-4)

Safety Data

• RIDADR: 2924
• HazardClass: 3/8
• PackingGroup: III
• Hazardous Substances Data: 61881-19-4(Hazardous Substances Data)

Usage

Description

2,2,2-Trifluoro-N-phenylacetimidoyl Chloride is an organic compound characterized by the presence of a trifluoromethyl group, a phenyl ring, and an imidoyl chloride functional group. It is a versatile reagent in organic synthesis, particularly in the formation of glycosidic bonds, due to its reactivity and stability.

Uses

Used in Organic Synthesis:
2,2,2-Trifluoro-N-phenylacetimidoyl Chloride is used as a reactant/reagent for the synthesis of oligo-fructopyranoside through regioselective glycosylation. This process involves the use of difructopyranosyl N-phenyltrifluoroacetimidate donor, which allows for the formation of specific glycosidic linkages in the target molecule.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride serves as a key intermediate for the preparation of various complex carbohydrate structures. Its unique reactivity enables the selective formation of glycosidic bonds, which is crucial for the synthesis of biologically active oligosaccharides and glycoconjugates.
Used in Pharmaceutical Industry:
2,2,2-Trifluoro-N-phenylacetimidoyl Chloride is used as a building block in the development of pharmaceutical compounds, particularly those targeting carbohydrate-based drug discovery. Its ability to form stable glycosidic linkages makes it a valuable tool in the synthesis of potential therapeutic agents with improved pharmacological properties.
Used in Material Science:
In material science, 2,2,2-Trifluoro-N-phenylacetimidoyl Chloride can be utilized in the synthesis of novel polymers and materials with specific properties. Its reactivity and stability contribute to the development of advanced materials with potential applications in various industries, such as electronics, coatings, and adhesives.

InChI:InChI=1/C8H5ClF3N/c9-7(8(10,11)12)13-6-4-2-1-3-5-6/h1-5H

Upstream product

• 61881-11-6 2,2,2-trifluoro-N-phenylethanethioamide 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 62-53-3 aniline 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 339276-14-1 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 

Relevant articles and documents

Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.

Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles

A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.

Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtai

Elemental Sulfur and Dimethyl Sulfoxide-Promoted Oxidative Cyclization of Trifluoroacetimidohydrazides with Methylhetarenes for the Synthesis of 3-Hetaryl-5-trifluoromethyl-1,2,4-triazoles

A metal-free approach for the synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles via sulfur/dimethyl sulfoxide-promoted oxidative cyclization of readily available trifluoroacetimidohydrazides with methylhetarenes has been developed. This transformation proceeds in cascade sulfur-mediated generation of thioaldehyde, condensation, intramolecular cyclization and oxidative aromatization sequence.