Dimethyl (2,6-dinitrophenyl)propanedioate

Base Information

• Chemical Name: Dimethyl (2,6-dinitrophenyl)propanedioate
• CAS No.: 86162-89-2
• Molecular Formula: C11H10N2O8
• Molecular Weight: 298.209
• DSSTox Substance ID: DTXSID90520989
• Mol file: 86162-89-2.mol

Synonyms:86162-89-2;Dimethyl (2,6-dinitrophenyl)propanedioate;SCHEMBL3536336;DTXSID90520989;WIAKOLJCYZCKDR-UHFFFAOYSA-N;dimethyl-2-(2,6-dinitrophenyl)-malonate

Chemical Property of Dimethyl (2,6-dinitrophenyl)propanedioate

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 298.04371528
• Heavy Atom Count: 21
• Complexity: 403

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C(C1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-])C(=O)OC

Technology Process of Dimethyl (2,6-dinitrophenyl)propanedioate

There total 4 articles about Dimethyl (2,6-dinitrophenyl)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: 90.0%

1-chloro-2,6-dinitrobenzene (606-21-3) + malonic acid dimethyl ester (108-59-8) → dimethyl (2,6-dinitrophenyl)malonate (86162-89-2)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl acetamide; at 90 ℃;

DOI:10.1016/j.bmcl.2010.02.086

Reference yield: 83.0%

meta-dinitrobenzene (99-65-0) + dimethyl 2-bromomalonate (868-26-8) → dimethyl (2,6-dinitrophenyl)malonate (86162-89-2)

Guidance literature:

With pyridine; potassium tert-butylate; copper(l) chloride; In 1,2-dimethoxyethane; at -20 - 0 ℃; for 2.5h; t-BuOCu in slight excess;

DOI:10.1055/s-1994-25447

Reference yield: 27.09%

malonic acid dimethyl ester (108-59-8) → dimethyl (2,6-dinitrophenyl)malonate (86162-89-2) + tert-butyl alcohol (75-65-0)

Guidance literature:

malonic acid dimethyl ester; With potassium tert-butylate; In DMF (N,N-dimethyl-formamide); at 20 - 90 ℃;

With nitric acid; at 0 ℃;

upstream raw materials:

1-chloro-2,6-dinitrobenzene

malonic acid dimethyl ester

meta-dinitrobenzene

dimethyl 2-bromomalonate

Downstream raw materials:

C₉H₁₂N₂O₂

2-(4-(trifluoromethyl)phenyl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-5-yl)acetamide

1-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-(2-oxoindolin-4-yl)urea

1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2-oxoindolin-4-yl)urea

Refernces

• 1、 Stump, Craig A.,Bell, Ian M.,Bednar, Rodney A.,Fay, John F.,Gallicchio, Steven N.,Hershey, James C.,Jelley, Richard,Kreatsoulas, Constantine,Moore, Eric L.,Mosser, Scott D.,Quigley, Amy G.,Roller, Shane A.,Salvatore, Christopher A.,Sharik, Steven S.,Theberge, Cory R.,Zartman, C. Blair,Kane, Stefanie A.,Graham, Samuel L.,Selnick, Harold G.,Vacca, Joseph P.,Williams, Theresa M.. "Identification of potent, highly constrained CGRP receptor antagonists". scheme or table. p. 2572 - 2576. Retrieved 2010/07/13.
• 2、 -. "HETEROCYCLICALLY SUBSTITUTED PENTANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, AND USE THEREOF AS ANTI-INFLAMMATORY AGENTS". Page/Page column 88. . Retrieved 2010/02/10.