Diethyl 2-(2-phenylhydrazono)malonate

Base Information

• Chemical Name: Diethyl 2-(2-phenylhydrazono)malonate
• CAS No.: 6134-59-4
• Molecular Formula: C13H16 N2 O4
• Molecular Weight: 264.281
• Hs Code.: 2928000090
• NSC Number: 2307
• DSSTox Substance ID: DTXSID30277425
• Nikkaji Number: J131.857H
• Mol file: 6134-59-4.mol

Synonyms:Diethyl 2-(2-phenylhydrazono)malonate;6134-59-4;2-(phenylhydrazono)malonic acid diethyl ester;diethyl 2-(phenylhydrazinylidene)propanedioate;Propanedioic acid, (phenylhydrazono)-, diethyl ester;NSC2307;Diethyl2-(2-phenylhydrazono)malonate;Temocaprilhydrochloride??;DTXSID30277425;NSC 2307;NSC-2307;Diethyl 2-(phenylhydrazono)malonate #;2-Phenylhydrazonomalonic acid diethyl ester;FT-0624818;Diethyl (2-phenylhydrazinylidene)propanedioate;Mesoxalic acid, diethyl ester, phenylhydrazone;Mesoxalic acid, phenylhydrazone, diethyl ester;A918501;Mesoxalic acid, diethyl ester, 2-(phenylhydrazone)

Chemical Property of Diethyl 2-(2-phenylhydrazono)malonate

Chemical Property:

• Vapor Pressure: 3.04E-05mmHg at 25°C
• Melting Point: 76-77 °C
• Boiling Point: 355.9°C at 760 mmHg
• PKA: 7.87±0.10(Predicted)
• Flash Point: 169°C
• PSA: 76.99000
• Density: 1.15g/cm³
• LogP: 1.65370
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 264.11100700
• Heavy Atom Count: 19
• Complexity: 316

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl2-(2-phenylhydrazono)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=NNC1=CC=CC=C1)C(=O)OCC

Technology Process of Diethyl 2-(2-phenylhydrazono)malonate

There total 5 articles about Diethyl 2-(2-phenylhydrazono)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: 95.0%

aniline (62-53-3) + diethyl malonate (105-53-3) → diethyl 2-(phenylhydrazono)malonate (6134-59-4)

Guidance literature:

aniline; With hydrogenchloride;

With sodium nitrite; In water; at 0 ℃;

diethyl malonate; With sodium acetate; In ethanol; water; Further stages.;

DOI:10.1021/jm070387h

Reference yield: 40.0%

sodium diethylmalonate (996-82-7,34727-00-9,73177-21-6) + benzene diazonium chloride (100-34-5) → phenylhydrazono-malonic acid monoethyl ester (40885-79-8) + ethyl phenylhydrazono(phenyl)acetate (52328-57-1) + phenylhydrazone of ethyl ester of glyoxalic acid (80447-71-8) + diethyl 2-(phenylhydrazono)malonate (6134-59-4)

Guidance literature:

In ethanol; water; at 0 - 5 ℃;

Reference yield:

aniline hydrochloride (142-04-1,36663-09-9) + diethyl malonate (105-53-3) → diethyl 2-(phenylhydrazono)malonate (6134-59-4)

Guidance literature:

Multistep reaction; (i) NaNO₂, (ii) /BRN= 774687/, aq. NaOAc;

DOI:10.1039/jr9610002828

upstream raw materials:

benzene diazonium chloride

diethyl malonate

aniline hydrochloride

sodium diethylmalonate

Downstream raw materials:

(N'-phenyl-hydrazino)-malonic acid monoethyl ester

phenylhydrazono-malonic acid monoethyl ester

(N'-phenyl-hydrazino)-acetic acid

2-(phenylhydrazono)-propanedioyl dichloride

Refernces

• 1、 Sereni, Laura,Tató, Marco,Sola, Francesco,Brill, Wolfgang K.-D.. "Solid phase synthesis of 6-acylamino-1-alkyl/aryl-4-oxo-1,4- dihydrocinnoline-3-carboxamides". . p. 8561 - 8577. Retrieved 2007/10/03.