59733-95-8

Basic information

• Product Name: ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE
• Synonyms: ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE
• CAS NO: 59733-95-8
• Molecular Formula: C₅H₅F₃N₂O₂
• Molecular Weight: 182.1
• Mol File: 59733-95-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 60-62°C/100mm
• Appearance: /
• CAS DataBase Reference: ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE(59733-95-8)
• EPA Substance Registry System: ETHYL 2-DIAZO-3,3,3-TRIFLUORO-PROPIONATE(59733-95-8)

Safety Data

• Hazardous Substances Data: 59733-95-8(Hazardous Substances Data)

Upstream product

• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 352-23-8 ethyl 3,3,3-trifluoropropanoate 
• 123220-98-4 C₁₂H₁₅F₃N₂O₅S 
• 1334313-60-8 (E)-ethyl 3,3,3-trifluoro-2-(2-tosylhydrazono)propanoate 

Downstream Products

• 134427-79-5 ethyl (2-phenylthio)-2-(trifluoromethyl)-4-pentynoate 
• 134427-73-9 ethyl 3-phenyl-2-(phenylthio)-2-(trifluoromethyl)-4-pentenoate 
• 134427-76-2 ethyl 2-(2-cyclohexen-1-yl)-2-(phenylthio)-3,3,3-trifluoropropionate 
• 134356-87-9 ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoropropanoate 
• 1334313-87-9 ethyl 2-(2-(benzyloxy)ethoxy)-3,3,3-trifluoropropanoate 

Relevant articles and documents

Enantioselective Synthesis of α-Trifluoromethyl Amines via Biocatalytic N-H Bond Insertion with Acceptor-Acceptor Carbene Donors

The biocatalytic toolbox has recently been expanded to include enzyme-catalyzed carbene transfer reactions not occurring in Nature. Herein, we report the development of a biocatalytic strategy for the synthesis of enantioenriched α-trifluoromethyl amines through an asymmetric N-H carbene insertion reaction catalyzed by engineered variants of cytochrome c552 from Hydrogenobacter thermophilus. Using a combination of protein and substrate engineering, this metalloprotein scaffold was redesigned to enable the synthesis of chiral α-trifluoromethyl amino esters with up to >99% yield and 95:5 er using benzyl 2-diazotrifluoropropanoate as the carbene donor. When the diazo reagent was varied, the enantioselectivity of the enzyme could be inverted to produce the opposite enantiomers of these products with up to 99.5:0.5 er. This methodology is applicable to a broad range of aryl amine substrates, and it can be leveraged to obtain chemoenzymatic access to enantioenriched β-trifluoromethyl-β-amino alcohols and halides. Computational analyses provide insights into the interplay of protein- and reagent-mediated control on the enantioselectivity of this reaction. This work introduces the first example of a biocatalytic N-H carbenoid insertion with an acceptor-acceptor carbene donor, and it offers a biocatalytic solution for the enantioselective synthesis of α-trifluoromethylated amines as valuable synthons for medicinal chemistry and the synthesis of bioactive molecules.

Rapid access to α-alkoxy and α-amino acid derivatives through safe continuous-flow generation of diazoesters

Microreactors: A highly efficient continuous-flow process has been developed for the synthesis of diazoesters from arylsulfonylhydrazones by means of in-flow Bamford-Stevens reactions. Furthermore, a range of α-alkoxy and α-amino acid derivatives have bee

Trifluoromethyl-Substituted Carbethoxy Carbene as a Novel CF3-Containing a2 Synthon Equivalent for the Preparation of 2-(Trifluoromethyl)-4-oxo Carboxylic Ester Derivative: Highly Functionalized Synthetic Building Blocks Bearing a CF3 Group

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