Diethyl (hydroxyimino)malonate

Base Information

• Chemical Name: Diethyl (hydroxyimino)malonate
• CAS No.: 6829-41-0
• Molecular Formula: C7H11NO5
• Molecular Weight: 189.168
• Hs Code.: 2928000090
• European Community (EC) Number: 633-262-5
• DSSTox Substance ID: DTXSID50423240
• Nikkaji Number: J1.624.500C
• Mol file: 6829-41-0.mol

Synonyms:6829-41-0;Diethyl Isonitrosomalonate;DIETHYL (HYDROXYIMINO)MALONATE;Diethyl 2-(hydroxyimino)malonate;diethyl 2-hydroxyiminopropanedioate;diethyl 2-hydroxyiminomalonate;DIETHYL OXIMINOMALONATE;Propanedioic acid, (hydroxyimino)-, diethyl ester;MFCD00019949;DiethylIsonitrosomalonate;Bis-(ethoxycarbonyl)hydroxyiminomethane;1,3-diethyl 2-(hydroxyimino)propanedioate;SCHEMBL2914885;DTXSID50423240;Diethyl 2-(hydroxyimino)malonate #;AC2236;hydroxyiminomalonic acid diethyl ester;AKOS005267137;CS-11236;SY011544;FT-0682691;A867076

Chemical Property of Diethyl (hydroxyimino)malonate

Chemical Property:

• Refractive Index: 1.4544 (estimate)
• Boiling Point: 324.41°C (rough estimate)
• PSA: 85.19000
• Density: 1.1821
• LogP: -0.05720
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 189.06372245
• Heavy Atom Count: 13
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

Diethyl(Hydroxyimino)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=NO)C(=O)OCC
• Uses: Diethyl (Hydroxyimino)malonate is a reagent used in the preparation of pyrano[2,?3-?e]?isoindol-?2-?one ring system, a heteroanalog of angelicin.

Technology Process of Diethyl (hydroxyimino)malonate

There total 10 articles about Diethyl (hydroxyimino)malonate 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: 98.4%

diethyl malonate (105-53-3) → diethyl oximinomalonate (6829-41-0)

Guidance literature:

With acetic acid; sodium nitrite; In water; ethyl acetate; at 0 - 25 ℃; for 22h;

Reference yield: 90.0%

→ diethyl oximinomalonate (6829-41-0)

Guidance literature:

With sodium hydroxide; In acetic acid; at 0 ℃; for 0.0833333h; Cooling with ice;

With sodium nitrite; In water; acetic acid; at 0 - 20 ℃; for 15h;

Reference yield: 72.0%

Diethyl ketomalonate (609-09-6) → diethyl oximinomalonate (6829-41-0)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; for 24h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2015.04.111

upstream raw materials:

n-Butyl nitrite

sodium diethylmalonate

methyl nitrite

diethyl malonate

Downstream raw materials:

ethyl 3,5-dimethyl-4-ethylpyrrole-2-carboxylate

diethyl 2-formylaminomalonate

2-(N-formamido)-2-benzylpropanedioic diethyl ester

1-Hydroxy-4-oxo-azetidine-2,2-dicarboxylic acid diethyl ester

Refernces

• 1、 -. "Preparation method of diethyl amino-malonate hydrochloride". Paragraph 0023. . Retrieved 2021/12/07.
• 2、 -. "3, 5-dimethyl-4-sulfonyl-1H-pyrrole compound as well as preparation method and application thereof". Paragraph 0019; 0049-0053. . Retrieved 2021/02/06.