Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate

Base Information

• Chemical Name: Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate
• CAS No.: 88975-07-9
• Molecular Formula: C15H19NO6
• Molecular Weight: 309.319
• DSSTox Substance ID: DTXSID90548547
• Wikidata: Q82427288
• Mol file: 88975-07-9.mol

Synonyms:88975-07-9;DTXSID90548547;Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate

Chemical Property of Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 309.12123733
• Heavy Atom Count: 22
• Complexity: 412

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C1=C(C=C(C=C1)[N+](=O)[O-])C)C(=O)OCC

Technology Process of Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate

There total 1 articles about Diethyl methyl(2-methyl-4-nitrophenyl)propanedioate 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: 60.0%

5-nitro-2-fluorotoluene (455-88-9) + Diethyl methylmalonate (609-08-5) → 2-Methyl-2-(2-methyl-4-nitro-phenyl)-malonic acid diethyl ester (88975-07-9)

Guidance literature:

DOI:10.1248/cpb.31.3424

Reference yield: 87.0%

2-Methyl-2-(2-methyl-4-nitro-phenyl)-malonic acid diethyl ester (88975-07-9) → 2-(4-Amino-2-methyl-phenyl)-2-methyl-malonic acid diethyl ester (88975-10-4)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1248/cpb.31.3424

Reference yield:

2-Methyl-2-(2-methyl-4-nitro-phenyl)-malonic acid diethyl ester (88975-07-9) → 2-Methyl-2-(2-methyl-4-thiocarbamoyloxy-phenyl)-malonic acid diethyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / H₂ / Pd-C

2: 1.) NaNO₂, H₂O/7.3percent H₂SO₄ / 1.) 0 deg C, 2 h; 2.) toluene, reflux, 15 min

3: triethylamine / diethyl ether / 2 h / -10 °C

4: H₂S/triethylamine / diethyl ether / 0.83 h / Ambient temperature

With sulfuric acid; hydrogen sulfide; water; hydrogen; triethylamine; sodium nitrite; palladium on activated charcoal; In diethyl ether;

DOI:10.1248/cpb.31.3424

upstream raw materials:

5-nitro-2-fluorotoluene

Diethyl methylmalonate

Downstream raw materials:

2-(4-Amino-2-methyl-phenyl)-2-methyl-malonic acid diethyl ester

2-(2-methyl-4-thiazol-2-yloxy-phenyl)-propionic acid

2-[2-methyl-4-(N-thiazol-2ylamino)phenyl]propionic acid

2-(4-Hydroxy-2-methyl-phenyl)-2-methyl-malonic acid diethyl ester

Refernces