Diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide

Base Information

• Chemical Name: Diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide
• CAS No.: 18417-40-8
• Molecular Formula: C8H12N2O6
• Molecular Weight: 230.177
• NSC Number: 98298
• Nikkaji Number: J1.915.209J
• Mol file: 18417-40-8.mol

Synonyms:18417-40-8;diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide;diethyl 2-oxido-1,2,5-oxadiazol-2-ium-3,4-dicarboxylate;2-Oxy-furazan-3,4-dicarboxylic acid diethyl ester;Diethyl 2-hydroxy-1,2.lambda.~5~,5-oxadiazole-3,4-dicarboxylate;bis(ethoxycarbonyl)furoxane;NCIOpen2_006486;SCHEMBL9684032;MFCD00184997;NSC-98298;STK689827;AKOS005602182;AS-6220;CS-0315088;diethyl1,2,5-oxadiazole-3,4-dicarboxylate2-oxide;3,4-Bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide;3,4-BIS(ETHOXYCARBONYL)-1,2,5-OXADIAZOL-2-IUM-2-OLATE

Chemical Property of Diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide

Chemical Property:

• Vapor Pressure: 0.000651mmHg at 25°C
• Boiling Point: 309.2°Cat760mmHg
• Flash Point: 140.8°C
• Density: 1.45g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 230.05388604
• Heavy Atom Count: 16
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=NO[N+](=C1C(=O)OCC)[O-]

Technology Process of Diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide

There total 17 articles about Diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide 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: 70.0%

ethyl acetoacetate (141-97-9) → nitroacetic acid ethyl ester (626-35-7) + diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide (18417-40-8)

Guidance literature:

ethyl acetoacetate; With sulfuric acid; nitric acid; In dichloromethane; at -5 - -3 ℃; Flow reactor;

With ethanol; at 30 ℃; Flow reactor;

DOI:10.1021/acs.joc.6b01634

Reference yield: 63.0%

α-ethoxycarbonylnitromethane sodium salt → diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide (18417-40-8) + ethyl 2-(hydroxyimino)-2-phenylacetate (131934-09-3,135765-81-0,712-41-4)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; benzene; at 0 ℃; for 2.5h;

DOI:10.1021/ja00004a044

Reference yield: 26.0%

1-(trimethyl-silyloxy)-3-phenyl-1-propene (51075-22-0) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → ethyl 4-benzylisoxazole-3-carboxylate (1332635-52-5) + diethyl 1,2,5-oxadiazole-3,4-dicarboxylate 2-oxide (18417-40-8)

Guidance literature:

1-(trimethyl-silyloxy)-3-phenyl-1-propene; ethyl 2-chloro-2-(hydroxyimino)acetate; With triethylamine; In hexane; at 20 ℃; Inert atmosphere;

With toluene-4-sulfonic acid; In hexane; at 70 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol202002r

upstream raw materials:

ethyl 2-(hydroxyimino)acetate

sodium acetylide

ethyl 2-chloro-2-(hydroxyimino)acetate

benzene

Downstream raw materials:

2,5-Dibenzyl-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

2,5-Bis-phenoxymethyl-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

2,5-Bis-(4-nitro-phenoxymethyl)-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

2,5-Bis-(naphthalen-2-yloxy)-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

Refernces

• 1、 Chentsova, Anna,Ushakov, Dmitry B.,Seeberger, Peter H.,Gilmore, Kerry. "Synthesis of α-Nitro Carbonyls via Nitrations in Flow". . p. 9415 - 9421. Retrieved 2016/10/17.
• 2、 Ohwada, Tomohiko,Yamagata, Naoko,Shudo, Koichi. "Friedel-Crafts-type reactions involving di- and tricationic species. Onium-allyl dications and O,O-diprotonated aci-nitro species bearing a protonated carbonyl group". . p. 1364 - 1373. Retrieved 2007/10/02.