442157-12-2

Basic information

• Product Name: ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate
• Synonyms: ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate
• CAS NO: 442157-12-2
• Molecular Weight: 238.218
• Mol File: 442157-12-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate(442157-12-2)
• EPA Substance Registry System: ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate(442157-12-2)

Safety Data

• Hazardous Substances Data: 442157-12-2(Hazardous Substances Data)

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 1999-00-4 ethyl 3-(4'-fluorophenyl)-3-oxopropionate 

Relevant articles and documents

An efficient aldol-type reaction of ethyl diazoacetate with aldehydes promoted by MgI2 etherate

The first example of the preparation of α-diazo-β-hydroxy esters by the aldol-type condensation of aldehydes with ethyl diazoacetate using Et3N as base in the presence of magnesium iodide etherate [MgI2.(Et2O)n] has been achieved in good to excellent yields at room temperature in CH2Cl2 in 15-30 min.

An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate

The aldol addition of acyldiazomethane with aromatic aldehydes, vinyl aldehyde and aliphatic aldehydes was carried out efficiently in the presence of MgI2 etherate and iPr2EtN (DIPEA) using untreated reagent-grade CH2Cl2 under atmospheric conditions in good to excellent yields. Iodide counterion and a non-coordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this reaction system.

Safe generation and direct use of diazoesters in flow chemistry

A safe and fast method for the production of β-hydroxy-α- diazoesters in continuous flow technology is described. The synthesis involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters in a three-step sequence. Georg Thieme Verlag Stuttgart · New York.