Diethyl ((m-chloroanilino)methylene)malonate

Base Information

• Chemical Name: Diethyl ((m-chloroanilino)methylene)malonate
• CAS No.: 3412-99-5
• Molecular Formula: C14H16 Cl N O4
• Molecular Weight: 297.738
• Hs Code.: 2922499990
• European Community (EC) Number: 222-301-8
• NSC Number: 3748
• UNII: VT5HT3L4XS
• DSSTox Substance ID: DTXSID70187711
• Nikkaji Number: J205.515E
• Mol file: 3412-99-5.mol

Synonyms:3412-99-5;Diethyl 2-(((3-chlorophenyl)amino)methylene)malonate;Diethyl ((m-chloroanilino)methylene)malonate;diethyl 2-[(3-chloroanilino)methylidene]propanedioate;VT5HT3L4XS;DIETHYL [(M-CHLOROANILINO)METHYLENE]MALONATE;NSC-3748;EINECS 222-301-8;MFCD00760212;AI3-18594;Diethyl 2-[[(3-Chlorophenyl)amino]methylene]malonate;Propanedioic acid, (((3-chlorophenyl)amino)methylene)-, diethyl ester;UNII-VT5HT3L4XS;(m-Chloroanilinomethylene)malonic acid, diethyl ester;SCHEMBL10862609;DTXSID70187711;NSC3748;NSC 3748;STK100167;AKOS000280915;AS-76750;SY271807;CS-0151913;FT-0698284;D81866;DIETHYL((3-CHLOROANILINO)METHYLENE)MALONATE;diethyl 2-[(3-chloroanilino)methylene]propanedioate;diethyl {[(3-chlorophenyl)amino]methylidene}propanedioate;[(3-Chlorophenylamino)methylene]propanedioic acid diethyl ester;1,3-DIETHYL 2-(((3-CHLOROPHENYL)AMINO)METHYLENE)PROPANEDIOATE;2-[[(3-chlorophenyl)amino]-methylene]-propanedioic acid diethyl ester;Propanedioic acid, 2-[[(3-chlorophenyl)amino]methylene]-, diethyl ester;3-(2-Ethoxycarbonyl-ethyl)-5-methyl-1H-pyrrole-2,4-dicarboxylicaciddiethylester;PROPANEDIOIC ACID, 2-(((3-CHLOROPHENYL)AMINO)METHYLENE)-, 1,3-DIETHYL ESTER

Chemical Property of Diethyl ((m-chloroanilino)methylene)malonate

Chemical Property:

• Vapor Pressure: 2.46E-05mmHg at 25°C
• Boiling Point: 358.9°Cat760mmHg
• Flash Point: 170.9°C
• PSA: 64.63000
• Density: 1.257g/cm³
• LogP: 2.83500
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 297.0767857
• Heavy Atom Count: 20
• Complexity: 350

Purity/Quality:

99% ^*data from raw suppliers

Diethyl2-(((3-chlorophenyl)amino)methylene)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CNC1=CC(=CC=C1)Cl)C(=O)OCC

Technology Process of Diethyl ((m-chloroanilino)methylene)malonate

There total 11 articles about Diethyl ((m-chloroanilino)methylene)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: 100.0%

3-chloro-aniline (108-42-9) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5)

Guidance literature:

In toluene; at 110 ℃; for 24h;

DOI:10.1016/j.bmc.2019.06.006

Reference yield: 80.0%

2-[2,2,2-trichloro-1-(3-chloro-phenylamino)-ethyl]-malonic acid diethyl ester (226881-90-9) → 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5)

Guidance literature:

With PEG-400; potassium carbonate; In acetonitrile; Heating;

DOI:10.1080/00397919908086168

Reference yield:

orthoformic acid triethyl ester (122-51-0) + 3-chloro-aniline (108-42-9) + diethyl malonate (105-53-3) → 2-(3-chlorophenylamino)methylenemalonic acid diethyl ester (3412-99-5)

Guidance literature:

With acetic anhydride; zinc(II) chloride; Yield given. Multistep reaction; 1.) reflux, 5 h, 2.) reflux, 30 min;

upstream raw materials:

3-chloro-aniline

diethyl 2-ethoxymethylenemalonate

N-(3-chloro-phenyl)-formimidic acid ethyl ester

diethyl malonate

Downstream raw materials:

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester

4,7-dichloroquinoline-3-carboxylic acid ethyl ester

ethyl 5-chloro-4-hydroxy-3-quinolinecarboxylate

7-chloro-4-piperazinylquinoline

Refernces

• 1、 Levai et al.. "". . p. 4003. Retrieved 1966.
• 2、 Eswaran, Sumesh,Shruthi, T. G.,Subramanian, Sangeetha. "Design, synthesis and study of antibacterial and antitubercular activity of quinoline hydrazone hybrids". . p. 137 - 147. Retrieved 2020/11/12.
• 3、 -. "Synthesis method of 4,7-dichloroquinoline". Paragraph 0020-0022; 0038-0040. . Retrieved 2020/07/15.