Acetic acid, benzoyldiazo-, ethyl ester

Base Information

• Chemical Name: Acetic acid, benzoyldiazo-, ethyl ester
• CAS No.: 28383-65-5
• Molecular Formula: C11H10N2O3
• Molecular Weight: 218.212
• Hs Code.: 2927000090
• DSSTox Substance ID: DTXSID001289643
• Nikkaji Number: J129.017G
• Mol file: 28383-65-5.mol

Synonyms:Acetic acid, benzoyldiazo-, ethyl ester;ethyl 2-diazo-3-oxo-3-phenylpropanoate;28383-65-5;Benzenepropanoic acid, .alpha.-diazo-.beta.-oxo-, ethyl ester;ethyl diazobenzoylacetate;2-diazo-3-oxo-3-phenyl-propionic acid ethyl ester;ethyl alpha-diazobenzoylacetate;DTXSID001289643;ethyl 2-diazo-3-oxo-3-phenylpropionate;Ethyl alpha-diazo-beta-oxobenzenepropanoate;alpha-Diazo-beta-oxobenzenepropanoic acid ethyl ester

Chemical Property of Acetic acid, benzoyldiazo-, ethyl ester

Chemical Property:

• PSA: 80.76000
• LogP: 1.18426
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 218.06914219
• Heavy Atom Count: 16
• Complexity: 326

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Acetic acid, benzoyldiazo-, ethyl ester

There total 14 articles about Acetic acid, benzoyldiazo-, ethyl ester 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%

4-acetamidobenzenesulfonyl azide (2158-14-7) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → ethyl 2-diazo-3-oxo-3-phenylpropanoate (28383-65-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1002/anie.202108899

Reference yield: 99.0%

ethyl 3-oxo-3-phenylpropionate (94-02-0) → ethyl 2-diazo-3-oxo-3-phenylpropanoate (28383-65-5)

Guidance literature:

With 4-acetamidobenzenesulfonyl azide; triethylamine; In acetonitrile; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2004.03.037

Reference yield: 93.0%

4-toluenesulfonyl azide (941-55-9) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → ethyl 2-diazo-3-oxo-3-phenylpropanoate (28383-65-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/acs.orglett.0c01811

upstream raw materials:

ethyl 3-oxo-3-phenylpropionate

cis-nitrous acid

methylmagnesium bromide

chloroformic acid ethyl ester

Downstream raw materials:

diazoacetic acid ethyl ester

benzoic acid

diethyl 2-phenylmalonate

ortoquinone

Refernces

• 1、 Cuevas-Ya?ez, Erick,Muchowski, Joseph M.,Cruz-Almanza, Raymundo. "Metalation of α-diazocarbonyl compounds using Grignard reagents. A convenient synthesis of α-diazo-β-ketoesters and mixed esters of α-diazomalonate". . p. 2417 - 2419. Retrieved 2004.
• 2、 Reyes, Yahaira,Mead, Keith T.. "Acetoxy-Substituted Cyclopropane Dicarbonyls as Stable Donor-Acceptor-Acceptor Cyclopropanes". . p. 3020 - 3026. Retrieved 2015.
• 3、 Fantinel, Mariane,Valiati, Nayara,Moro, Pedro A.M.,Sá, Marcus M.. "Amino-modified Merrifield resins as recyclable catalysts for the safe and sustainable preparation of functionalized α-diazo carbonyl compounds". . . Retrieved 2021/03/30.
• 4、 Jha, Neha,Singh, Roushan Prakash,Saxena, Paridhi,Kapur, Manmohan. "Iridium(III)-Catalyzed C(3)-H Alkylation of Isoquinolines via Metal Carbene Migratory Insertion". supporting information. p. 8694 - 8698. Retrieved 2021/11/24.