Diethyl 2-((phenylamino)methylene)malonate

Base Information

• Chemical Name: Diethyl 2-((phenylamino)methylene)malonate
• CAS No.: 54535-22-7
• Molecular Formula: C14H17 N O4
• Molecular Weight: 263.293
• Hs Code.: 2922499990
• European Community (EC) Number: 651-261-8
• NSC Number: 99383
• DSSTox Substance ID: DTXSID70295042
• Nikkaji Number: J866.081F
• Mol file: 54535-22-7.mol

Synonyms:54535-22-7;Diethyl 2-((phenylamino)methylene)malonate;Diethyl anilinomethylenemalonate;Diethyl 2-(anilinomethylene)malonate;diethyl 2-(anilinomethylidene)propanedioate;2-phenylaminomethylene-malonic acid diethyl ester;2-PHENYLAMINOMETHYLENE-MALONIC ACIDDIETHYL ESTER;1,3-diethyl 2-[(phenylamino)methylidene]propanedioate;diethyl (anilinomethylene)malonate;Diethyl2-((phenylamino)methylene)malonate;2-phenylaminomethylenemalonic acid diethyl ester;NCIOpen2_006517;SCHEMBL395324;DTXSID70295042;Propanedioic acid, [(phenylamino)methylene]-, diethyl ester;NSC99383;MFCD00173404;NSC-99383;STL471947;AKOS001592756;Diethyl 2-(anilinomethylene)malonate #;s11929;CS-0151912;FT-0622399;6J-048;diethyl [(phenylamino)methylidene]propanedioate;A918093;AE-641/30076011;SR-01000391923;SR-01000391923-1;F1967-1625;(S)-3-((2S,4R)-4-Bromo-4-((2S,4S)-tetrahydro-4-isopropyl-5-oxofuran-2-yl)-2-isopropylbutanoyl)-4-benzyloxazolidin-2-one

Chemical Property of Diethyl 2-((phenylamino)methylene)malonate

Chemical Property:

• Vapor Pressure: 0.00013mmHg at 25°C
• Melting Point: 94-95 °C
• Boiling Point: 334.2°C at 760 mmHg
• PKA: -0.80±0.70(Predicted)
• Flash Point: 155.9°C
• PSA: 64.63000
• Density: 1.171g/cm³
• LogP: 2.18160
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 312

Purity/Quality:

99% ^*data from raw suppliers

Diethyl2-((phenylamino)methylene)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl 2-((phenylamino)methylene)malonate

There total 18 articles about Diethyl 2-((phenylamino)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%

aniline (62-53-3) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl (anilinomethylene)malonate (54535-22-7)

Guidance literature:

at 120 - 130 ℃; for 16.5h; Temperature;

Reference yield: 100.0%

allyl bromide (106-95-6) + aniline (62-53-3) + diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl (anilinomethylene)malonate (54535-22-7)

Guidance literature:

allyl bromide; With indium; In tetrahydrofuran; at 20 ℃; for 1h;

aniline; diethyl 2-ethoxymethylenemalonate; In tetrahydrofuran; for 2h;

DOI:10.1021/ol052326o

Reference yield: 82.0%

2-(2,2,2-trichloro-1-phenylamino-ethyl)-malonic acid diethyl ester (226881-88-5) → diethyl (anilinomethylene)malonate (54535-22-7)

Guidance literature:

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

DOI:10.1080/00397919908086168

upstream raw materials:

propene-1,1,3,3-tetracarboxylic acid tetraethyl ester

aniline

diethyl 2-ethoxymethylenemalonate

Diazoethan

Downstream raw materials:

1-benzyloxycarbonyl-3-carboethoxy-1,4-dihydroquinolin-4-one

(1R^*,4aS^*,10aS^*)-5-benzyloxycarbonyl-10a-ethoxycarbonyl-1-methoxy-3,10-dioxo-octahydroacridine

1-carboethoxy-2-<1,3-biscarboethoxy-4-hydroxy-1,2-dihydroquinolin-2-yl>methyl-4-methoxycyclohexa-1,3-diene

1-carboethoxy-2-<1-carbobenzyloxy-3-carboethoxy-4-hydroxy-1,2-dihydroquinolin-2-yl>methyl-4-methoxycyclohexa-1,3-diene

Refernces

• 1、 Venkatesan, Perumal,Thamotharan, Subbiah,Percino, M. Judith,Ilangovan, Andivelu. "Crystal Packing Modulation of the Strength of Resonance-Assisted Hydrogen Bonds and the Role of Resonance-Assisted Pseudoring Stacking in Geminal Amido Esters: Study Based on Crystallography and Theoretical Calculations". . p. 779 - 798. Retrieved 2021/01/13.
• 2、 Abdelgawad, Mohamed A.,Al-Sanea, Mohammad M.,Alharbi, Khalid S.,Ali Farahat, Ibrahim,Alzarea, Abdulaziz I.,Alzarea, Sami I.,Bakr, Rania B,El Kerdawy, Ahmed M.,Eldehna, Wagdy M.,Elkamhawy, Ahmed,Elshemy, Heba A. H.,Joo Roh, Eun,Lee, Kyeong,Paik, Sora,Syed Nasir Abbas, Bukhari. "Sulfonamide-based 4-anilinoquinoline derivatives as novel dual Aurora kinase (AURKA/B) inhibitors: Synthesis, biological evaluation and in silico insights". . . Retrieved 2020/05/08.