6111-99-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Diazopropanoic acid ethyl ester is used as a synthetic intermediate for the production of pharmaceuticals. Its ability to introduce the diazo functional group into other molecules makes it a valuable reagent in the synthesis of various drugs, contributing to the development of new medications and therapies.
Used in Dye Industry:
In the dye industry, 2-Diazopropanoic acid ethyl ester is used as a key component in the synthesis of dyes. Its reactivity allows for the creation of a wide range of colored compounds, which are utilized in various applications such as textiles, printing inks, and pigments.
Used in Organic Chemistry Research:
2-Diazopropanoic acid ethyl ester is used as a research reagent in organic chemistry. Its highly reactive nature and ability to introduce the diazo functional group make it an essential tool for chemists studying the properties and reactions of various organic compounds.
Used in Synthesis of Other Organic Compounds:
2-Diazopropanoic acid ethyl ester is used as a reagent in the synthesis of other organic compounds, such as agrochemicals, fragrances, and flavorings. Its versatility in introducing the diazo functional group enables the creation of a diverse range of products across different industries.
It is important for researchers and handlers to exercise caution when working with 2-Diazopropanoic acid ethyl ester due to its explosive nature. Proper safety measures and handling procedures should be followed to minimize risks and ensure a safe working environment.

Upstream product

• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 27772-62-9 ethyl 2-formylpropionate 
• 111466-76-3 N-Ethoxycarbonyl-N-nitroso-2-amino-propionsaeure-ethylester 
• 95204-49-2 ethyl N-methoxycarbonyl-N-nitrosoalaninate 
• 169383-53-3 ethyl 2-hydrazonopropanoate 
• 941-55-9 4-toluenesulfonyl azide 
• 121811-29-8 ethyl 2-methyl-3-oxopentanoate 
• 535-11-5 Ethyl 2-bromopropionate 
• 105-37-3 Ethyl propionate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 95204-53-8 MeOCO-AlaOEt 
• 10488-87-6 ethyl 2-benzoylpropionate 
• 54843-13-9 3-hydroxy-2-methylacrylic acid ethyl ester 
• 17344-99-9 AlaOEt 

Downstream Products

• 97-64-3 ethyl 2-hydroxypropionate 
• 22644-89-9 diethyl (Z)-2,3-dimethylbutenedioate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 65354-74-7 1-Methyl-2-isopropylidencyclopropancarbonsaeureethylester 
• 65354-75-8 1,2,2-Trimethyl-3-methylene-cyclopropanecarboxylic acid ethyl ester 
• 60153-81-3 (1R,6S,7R)-7-Methyl-bicyclo[4.1.0]heptane-7-carboxylic acid ethyl ester 
• 130121-11-8 ethyl exo-6-methyl-2-oxabicyclo<3.1.0>hex-3-ene-6-carboxylate 
• 130121-12-9 ethyl 2-methyl-6-oxo-2(E),4(Z)-hexadienoate 
• 130121-15-2 Ethyl (2E,4E)-2-methyl-6-oxohexa-2,4-dienoate 
• 148431-23-6 2-Diazo-3-oxo-4-<5-oxo-2,2-bis(trifluormethyl)-1,3-oxazolidin-3-yl>-butansaeureethylester 
• 148431-35-0 5-(<5-Oxo-2,2-bis(trifluormethyl)-1,3-oxazolidin-3-yl>-acetylamino)-1,2,3-thiadiazol-4-carbonsaeure-ethylester 
• 82706-96-5 (Z)-ethyl 2-cyano-1,2-dimethylcyclopropanecarboxylate 
• 82706-95-4 (E)-ethyl 2-cyano-1,2-dimethylcyclopropanecarboxylate 
• 82706-93-2 (3S,5S)-5-Cyano-3,5-dimethyl-4,5-dihydro-3H-pyrazole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Copper-Catalyzed Regioselective Coupling of Tosylhydrazones and 2-Pyridones: A Strategy for the Production of N-Alkylated Compounds

The highly regioselective N-alkylation reaction of 2-pyridones was achieved through hydrazone chemistry, especially for substrates with bulky secondary alkyl groups. Described herein is a copper-catalyzed coupling reaction of pyridone derivatives with tosylhydrazones.

Copper-catalyzed oxyvinylation of diazo compounds

A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering polyfunctionalized vinylated products. The strategy was successfully extended to a three-component/intermolecular version with alcohols. The obtained products contain synthetically versatile functional groups, such as an aryl iodide, an ester, and an allylic leaving group, enabling further modification.

Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers

Multicomponent reactions provide efficient means to access molecular complexity. Herein, we report a copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers. Extensive variations of the three partners of the reaction is possible, leading to highly functionalized and structurally diverse products under mild conditions. Alkynylation of a copper ylide intermediate is postulated as key step for this transformation.

Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds

The catalytic insertion of copper carbenoids into O-H bonds affords synthetically useful α-alkyl/aryl-α-alkoxy/aryloxy derivatives. Herein, the design, preparation and application of supramolecularly regulated copper(i) complexes of bisoxazoline ligands is reported. We have demonstrated that the catalytic performance of these systems can be modulated by the use of an external molecule (i.e.the regulation agent), which interacts with a polyethyleneoxy chain on the ligand (i.e.the regulation site)viasupramolecular interactions. This approach has been applied to an array of structurally diverse alcohols (cycloalkyl, alkyl and aryl derivatives). Moreover, we have used this methodology to synthesise advanced synthetic intermediates of biologically relevant compounds.

Cross coupling of sulfonyl radicals with silver-based carbenes: A simple approach to β-carbonyl arylsulfones

A coupling reaction between sulfonyl radicals and silver-based carbenes has been well established. This simple radical-carbene coupling (RCC) process provided an efficient approach to a variety of β-carbonyl arylsulfones from sodium arylsulfinates and diazo compounds, and was characterized by wide substrate scope, easy scale-up, simple manipulation, accessible starting materials, and mild reaction conditions.

Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5- epi-Cycloclavine

Starting from the commercially available 4-bromoindole, a concise and efficient enantioselective formal synthesis of (+)-cycloclavine (1) in 13 steps with 2.0% overall yield and a total synthesis of (+)-5-epi-cycloclavine (2) in 14 steps with 3.3% overall yield were achieved. Key features of the syntheses include the addition of a Grignard reagent to the C-N/Heck reaction sequence to construct the fused 6-5-6 ring systems, cyclopropanation, an ester aminolysis reaction, and the first example of the construction of a 3-azabicyclo[3,1,0]hexane through an intramolecular [3 + 2] cycloaddition/nitrogen extrusion.

Metal-Free Tandem Rearrangement/Lactonization: Access to 3,3-Disubstituted Benzofuran-2-(3H)-ones

A novel metal-free synthesis of 3,3-disubstituted benzofuran-2-(3H)-ones through reacting α-aryl-α-diazoacetates with triarylboranes is presented. Initially, triarylboranes were successfully investigated in α-arylations of α-diazoacetates, however in the presence of a heteroatom in the ortho position, the boron enolate intermediate undergoes an intramolecular rearrangement to form a quaternary center. The intermediate cyclizes to afford valuable 3,3-disubstituted benzofuranones in good yields.

Synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives: Via a multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate

We report a green synthesis of spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives which are of potential value in medicinal chemistry. We are able to access spiro[2,3-dihydrofuran-3,3′-oxindole] derivatives via a Cu(OTf)2-catalyzed or Cu(OTf)2/Rh2(OAc)4-cocatalyzed multi-component cascade reaction of α-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate. The reaction can be accomplished in good to excellent yields (60-99%), and the structure of products 6a and 6k was supported by X-ray crystallography. The catalyst Cu(OTf)2 can be recycled 4 times without a sharp loss of the yield of 6a. 6q can be easily synthesized in gram scale. In brief, the reaction is characterized by step economy, a harmless solvent, and a recyclable catalyst.

A sustainable catalytic enantioselective synthesis of norstatine derivatives

Norstatine derivatives are of important value in pharmaceutical science. However, their catalytic asymmetric synthesis is rare. We developed a sustainable method via chiral phosphoric acid (CPA)-[Rh(OAc)2]2 co-catalyzed multi-component reactions (MCR) of diazoacetates with alcohol/water and imines. This method allows us to synthesize a library of 45 norstatines with excellent enanotioselectivites and broad substrate scope which includes anti-α-aryl-norstatines 11-1, anti-α-alkyl-norstatines 11-2, syn-α-hydro-norstatines 11-3 and syn-α-aryl-norstatines 11-4. The sustainability of this method lies in the reliable scalability, improved safety, and reusable [Rh(OAc)2]2 catalyst. The synthetic value of norstatine derivatives was demonstrated by preparing oxazolinone 14, ezetimibe analogue 15, and Taxol C-13 chain 16. Mechanistic study reveals that the synergetic catalysis of CPA and [Rh(OAc)2]2 is essential to maintain chemo- and enantioselectivity. Control experiments support the mechanism where the reactions proceed through the trapping of hyper-reactive oxonium ylides with imines. Shortly, we report herein the sustainable catalytic enantioselective synthesis of both syn- and anti-norstatine derivatives. We believe that this method might shed light on the sustainable synthesis of norstatine derivative-based drug candidates.

Au Nanoparticle-Catalyzed Insertion of Carbenes from α-Diazocarbonyl Compounds into Hydrosilanes

Supported Au nanoparticles on TiO2 catalyze the insertion of carbenes from α-diazocabonyl compounds into hydrosilanes. It is proposed that the transformation involves two modes of catalytic activation: formation of nucleophilic Au carbenes on the surface of nanoparticle via expulsion of N2 and activation of the Si-H bond of hydrosilane on Au nanoparticle, followed by coupling of the chemisorbed species. No external ligands or additives are required, while the process is purely heterogeneous, thus allowing the recycling and reuse of the catalyst.