Ethyl 2-diazo-2-phenylacetate

Base Information

• Chemical Name: Ethyl 2-diazo-2-phenylacetate
• CAS No.: 22065-57-2
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.202
• Hs Code.: 2927000090
• DSSTox Substance ID: DTXSID10694878
• Nikkaji Number: J1.845.692C
• Mol file: 22065-57-2.mol

Synonyms:22065-57-2;Ethyl 2-diazo-2-phenylacetate;ETHYL DIAZOPHENYLACETATE;Ethyl diazo(phenyl)acetate;ethyl 2-phenyldiazoacetate;Ethyl2-diazo-2-phenylacetate;diazophenylacetic acid ethyl ester;DTXSID10694878;DYCIOVIEGYZBJP-UHFFFAOYSA-N;Phenyldiazoacetic acid ethyl ester;AKOS006306020;2-diazonio-1-ethoxy-2-phenyl-ethenolate;2-Diazonio-1-ethoxy-2-phenylethen-1-olate;A815893

Chemical Property of Ethyl 2-diazo-2-phenylacetate

Chemical Property:

• PSA: 63.69000
• LogP: 1.34966
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 190.074227566
• Heavy Atom Count: 14
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

ETHYL DIAZOPHENYLACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=[N+]=[N-])C1=CC=CC=C1

Technology Process of Ethyl 2-diazo-2-phenylacetate

There total 25 articles about Ethyl 2-diazo-2-phenylacetate 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: 99.0%

syn-Ethyl phenylglyoxylate hydrazone → ethyl 2-phenyldiazoacetate (22065-57-2)

Guidance literature:

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

DOI:10.1002/chem.201500118

Reference yield: 97.0%

phenylglyoxylic acid ethyl ester (1603-79-8) → ethyl 2-phenyldiazoacetate (22065-57-2)

Guidance literature:

phenylglyoxylic 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: 96.0%

C16H15N3O6S → ethyl 2-phenyldiazoacetate (22065-57-2)

Guidance literature:

With sodium hydride; In 1,4-dioxane; mineral oil; at 30 ℃; for 12h; Inert atmosphere;

upstream raw materials:

ethyl 3-oxo-2-phenylpropanoate

ethyl 2-phenyl-2-aminoacetate

ethyl 2-phenyl-2-(2-tosylhydrazono)acetate

diazoacetic acid ethyl ester

Downstream raw materials:

ethyl 2-phenyl-2-(piperidin-1-yl)acetate

ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)-2-phenylacetate

ethyl 2-(2-fluorophenylamino)-2-phenylacetate

ethyl 2-((tert-butoxycarbonyl)amino)-2-phenylacetate

Refernces

• 1、 Rodríguez, Anabel M.,Molina, Francisco,Díaz-Requejo, M. Mar,Pérez, Pedro J.. "Copper-Catalyzed Selective Pyrrole Functionalization by Carbene Transfer Reaction". . p. 1998 - 2004. Retrieved 2020.
• 2、 Umezu, Satoshi,dos Passos Gomes, Gabriel,Yoshinaga, Tatsuro,Sakae, Mikei,Matsumoto, Kenji,Iwata, Takayuki,Alabugin, Igor,Shindo, Mitsuru. "Regioselective One-Pot Synthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates". . p. 1298 - 1302. Retrieved 2017.
• 3、 Zhao, Yan-Rui,Li, Lei,Xu, Guo-Yong,Xuan, Jun. "All-Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation". supporting information. p. 506 - 511. Retrieved 2021/12/08.
• 4、 Cheng, Xiao,Cai, Bao-Gui,Mao, Hui,Lu, Juan,Li, Lei,Wang, Kun,Xuan, Jun. "Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation". supporting information. p. 4109 - 4114. Retrieved 2021/05/26.