Ethyl azidoacetate

Base Information

• Chemical Name: Ethyl azidoacetate
• CAS No.: 637-81-0
• Molecular Formula: C4H7N3O2
• Molecular Weight: 129.118
• Hs Code.: 2929909090
• European Community (EC) Number: 211-301-3
• NSC Number: 84132
• DSSTox Substance ID: DTXSID30213101
• Nikkaji Number: J205.911H
• Wikidata: Q72472755
• Mol file: 637-81-0.mol

Synonyms:Ethyl azidoacetate;637-81-0;Ethyl 2-azidoacetate;Azidoacetic acid ethyl ester;Acetic acid, azido-, ethyl ester;Azido-acetic acid ethyl ester;CCRIS 3368;EINECS 211-301-3;Acetic acid, 2-azido-, ethyl ester;BRN 4247209;C4H7N3O2;Azido-aceticaciethylester;Ethylazidoacetate;MFCD00190177;ethyl azido-acetate;Acetic acid, 2-azido-,ethyl ester;ethyl-2-azidoacetate;ethyl alpha-azidoacetate;NCIOpen2_000977;azido acetic acid ethyl ester;SCHEMBL13431922;DTXSID30213101;NSC84132;NSC 84132;NSC-84132;AKOS005259752;(2-ethoxy-2-oxo-ethyl)imino-imino-ammonium;E1255;FT-0626163;Azidoacetic acid ethyl ester, 25% in toluene;EN300-37371;A834524;J-640294;J-800298

Chemical Property of Ethyl azidoacetate

Chemical Property:

• Appearance/Colour: Colorless or light yellow liquid
• Refractive Index: 1.4330 to 1.4370
• Boiling Point: 44-46 °C 2mm
• Flash Point: 7 °C
• PSA: 76.05000
• Density: 1.127 g/mL at 25 °C
• LogP: 0.31256
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 129.053826475
• Heavy Atom Count: 9
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2-Azidoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,C
• Hazard Codes: Xn,Xi,C,F
• Statements: 1-40-36/37/38-10-67-65-63-48/20-38-11
• Safety Statements: 7-16-26-35-36-47-62-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CN=[N+]=[N-]
• General Description: ETHYL AZIDOACETATE is an organic azide compound that participates efficiently in CuSO₄-catalyzed Huisgen-click reactions, forming 1,4-disubstituted triazoles with high regioselectivity and yield under thermal conditions in water. It reacts readily with alkynes, such as propargyl phenyl ether, to produce triazole derivatives, demonstrating its utility as a key reactant in click chemistry applications. ETHYL AZIDOACETATE's reactivity and compatibility with aqueous conditions make it valuable for one-pot multicomponent syntheses.

Technology Process of Ethyl azidoacetate

There total 10 articles about Ethyl azidoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl bromoacetate (105-36-2) → ethyl-2-azidoacetate (637-81-0)

Guidance literature:

With sodium azide; In water; acetone; at 20 ℃; for 0.5h;

DOI:10.1021/ol800675u

Reference yield: 98.0%

chloroacetic acid ethyl ester (105-39-5) → ethyl-2-azidoacetate (637-81-0)

Guidance literature:

With sodium azide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; at 20 ℃; for 25h; Inert atmosphere;

DOI:10.1002/chem.200903484

Reference yield: 60.0%

trimethylsilylazide (4648-54-8) + chloroacetic acid ethyl ester (105-39-5) → ethyl-2-azidoacetate (637-81-0)

Guidance literature:

DOI:10.1246/cl.1982.1477

upstream raw materials:

(N-nitroso-hydrazino)-acetic acid ethyl ester

chloroacetic acid ethyl ester

GlyOEt*HCl

ethyl iodoacetae

Downstream raw materials:

triphenylphosphine imine ethyl acetate

α-azido-N-methylacetamide

ethyl N-isobutyrylglycinate

5-ethoxy-2-phenyl-1,3-oxazole

Refernces

A simple, efficient thermally promoted protocol for Huisgen-click reaction catalyzed by CuSO₄·5H₂O in water

10.1016/j.tetlet.2014.02.108

The study presents a thermally promoted and CuSO4-catalyzed protocol for the Huisgen-click reaction in water. The chemicals involved include organic azides and alkynes as reactants, with CuSO4·5H2O serving as the catalyst. The protocol is efficient, with the reaction between propargyl phenyl ether and ethyl azidoacetate yielding a product in 85% yield within 30 minutes at 100°C. The study also explores the regioselectivity of the reaction, finding that CuSO4·5H2O provides the best regioselectivity among tested Cu(II) catalysts, favoring the formation of 1,4-disubstituted triazoles. Additionally, the protocol is extended to a one-pot three-component reaction involving alkyl halides, NaN3, and alkynes, where NaN3 acts as both an azidonation reagent and a reducing agent for Cu(II), facilitating the in situ generation of Cu(I) necessary for the reaction. This method is proven to be suitable for a wide range of substrates, yielding products in excellent yields, and represents a significant advancement in the field of Huisgen-click chemistry.

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