Ethyl 2-diazopropanoate

Base Information

• Chemical Name: Ethyl 2-diazopropanoate
• CAS No.: 6111-99-5
• Molecular Formula: C5H8N2O2
• Molecular Weight: 128.131
• Hs Code.: 2927000090
• DSSTox Substance ID: DTXSID80702919
• Nikkaji Number: J81.146G
• Mol file: 6111-99-5.mol

Synonyms:ethyl 2-diazopropanoate;6111-99-5;2-Diazonio-1-ethoxyprop-1-en-1-olate;2-Diazopropanoic acid ethyl ester;ethyl 2-diazopropionate;DTXSID80702919;2-Diazopropionic acid ethyl ester;YRYGWFQYKCXDNA-UHFFFAOYSA-N;2-diazo-propionic acid ethyl ester;AKOS023412482;AT25590;EN300-1074291;A928573

Chemical Property of Ethyl 2-diazopropanoate

Chemical Property:

• Refractive Index: 1.4472 (estimate)
• Boiling Point: 237.54°C (rough estimate)
• PSA: 63.69000
• Density: 1.0860
• LogP: 0.32126
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 128.058577502
• Heavy Atom Count: 9
• Complexity: 158

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=[N+]=[N-])C

Technology Process of Ethyl 2-diazopropanoate

There total 18 articles about Ethyl 2-diazopropanoate 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: 96.0%

2-oxo-propionic acid ethyl ester (617-35-6) → ethyl diazoalaninate (6111-99-5)

Guidance literature:

2-oxo-propionic acid ethyl ester; With benzoic acid; hydrazine; In tetrahydrofuran; at 20 ℃; for 16h;

With N-iodo-N-potassio-p-toluenesulphonamide; potassium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/chem.201304656

Reference yield: 92.0%

ethyl 2-hydrazonopropanoate (169383-53-3) → ethyl diazoalaninate (6111-99-5)

Guidance literature:

With Polystyrene supported potassium N-iodosulfonamide resin; In dichloromethane; Inert atmosphere;

DOI:10.1002/chem.201500118

Reference yield: 87.0%

ethyl 2-(2-tosylhydrazono)propanoate → ethyl diazoalaninate (6111-99-5)

Guidance literature:

ethyl 2-(2-tosylhydrazono)propanoate; With sodium methylate; In methanol;

at 90 - 220 ℃; for 1h; Pyrolysis;

DOI:10.15227/orgsyn.064.0207

upstream raw materials:

AlaOEt

2-acetylpropanoic acid ethyl ester

ethyl 2-formylpropionate

3-hydroxy-2-methylacrylic acid ethyl ester

Downstream raw materials:

ethyl exo-6-methyl-2-oxabicyclo<3.1.0>hex-3-ene-6-carboxylate

ethyl 2-methyl-6-oxo-2(E),4(Z)-hexadienoate

Ethyl (2E,4E)-2-methyl-6-oxohexa-2,4-dienoate

ethyl 2-methyl-6-oxo-2(E),4(Z)-heptadienoate

Refernces

• 1、 Pisella, Guillaume,Gagnebin, Alec,Waser, Jerome. "Copper-catalyzed oxyvinylation of diazo compounds". supporting information. p. 3884 - 3889. Retrieved 2020/05/14.
• 2、 Iniesta, Ester,Vidal-Ferran, Anton. "Supramolecularly regulated copper-bisoxazoline catalysts for the efficient insertion of carbenoid species into hydroxyl bonds". supporting information. p. 6364 - 6367. Retrieved 2020/06/21.