2-(Methoxycarbonyl)-6-nitrobenzoic acid

Base Information

• Chemical Name: 2-(Methoxycarbonyl)-6-nitrobenzoic acid
• CAS No.: 21606-04-2
• Molecular Formula: C9H7NO6
• Molecular Weight: 225.158
• Hs Code.: 2918990090
• European Community (EC) Number: 606-804-3
• DSSTox Substance ID: DTXSID30402851
• Nikkaji Number: J1.637.809G
• Wikidata: Q72493739
• Mol file: 21606-04-2.mol

Synonyms:21606-04-2;2-(methoxycarbonyl)-6-nitrobenzoic acid;1-Methyl-3-nitrophthalate;2-methoxycarbonyl-6-nitrobenzoic acid;2-Nitro-6-methoxycarbonyl benzoic acid;MFCD00034781;1,2-BENZENEDICARBOXYLIC ACID, 3-NITRO-1-METHYL ESTER;Methyl 2-carboxy-3-nitrobenzoate;3-Nitro-phthalic acid 1-Methyl ester;2-(Methoxycarbonyl)-6-nitrobenzoicAcid;SCHEMBL2598194;DTXSID30402851;1-METHYL 3-NITROPHTHALATE;DJMQLZPEBHSABD-UHFFFAOYSA-N;3-Nitrophthalic acid 1-methyl ester;AKOS002268896;AC-4830;AM84761;CS-W013046;DS-16336;SY025404;A4643;FT-0656679;M2795;EN300-1626394;3-Nitro-1,2-Benzenedicarboxylic Acid Monomethyl Ester

Chemical Property of 2-(Methoxycarbonyl)-6-nitrobenzoic acid

Chemical Property:

• Vapor Pressure: 1.98E-07mmHg at 25°C
• Melting Point: 160.0 to 164.0 °C
• Refractive Index: 1.594
• Boiling Point: 409.199 °C at 760 mmHg
• PKA: 1.87±0.30(Predicted)
• Flash Point: 201.277 °C
• PSA: 109.42000
• Density: 1.484 g/cm³
• LogP: 1.60280
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 225.02733694
• Heavy Atom Count: 16
• Complexity: 310

Purity/Quality:

≥98.0%(HPLC) ^*data from raw suppliers

Methyl3-Nitrophthalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C(=CC=C1)[N+](=O)[O-])C(=O)O
• Uses: Methyl 3-Nitrophthalate is an intermediate in the synthesis of (αS)-3-Ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]-N-[(1S)-1-phenylethyl]-benzenemethanamine which is an impurity of Apremilast (A729700), which is an oral phosphodiesterase 4 inhibitor used for treating psoriatic arthritis.

Technology Process of 2-(Methoxycarbonyl)-6-nitrobenzoic acid

There total 11 articles about 2-(Methoxycarbonyl)-6-nitrobenzoic acid 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: 98.4%

methanol (67-56-1) + 3-nitrophthalic acid (603-11-2) → methyl 2-carboxy-3-nitrobenzoate (21606-04-2)

Guidance literature:

With thionyl chloride; at 5 ℃; for 20 - 25h; Heating / reflux;

Reference yield: 94.7%

3-nitrophthalic acid (603-11-2) + trimethyl orthoformate (149-73-5) → methyl 2-carboxy-3-nitrobenzoate (21606-04-2)

Guidance literature:

With sulfuric acid; In methanol; at 59 - 65 ℃; for 15 - 20h; Heating / reflux; Industry scale;

Reference yield: 90.0%

dimethyl 3-nitrophthalate (13365-26-9) → methyl 2-carboxy-3-nitrobenzoate (21606-04-2)

Guidance literature:

at 20 ℃; for 2h; Acidic conditions;

upstream raw materials:

methanol

3-nitrophthalic acid

3-nitrophthalic acid anhydride

sodium methylate

Downstream raw materials:

acid chloride of 1-methylhydrogen-3-nitrophthalate

2-(methoxycarbonyl)-6-aminobenzoic acid

2-carbamoyl-6-nitrobenzoic acid

2-(methoxycarbonyl)-3-nitrobenzoic acid

Refernces

• 1、 -. "A 2 - ethoxy benzimidazole - 7 - carboxylic acid methyl ester". Paragraph 0033; 0040-0043. . Retrieved 2018/05/24.
• 2、 -. "BICYCLIC ARYL AND HETEROARYL COMPOUNDS FOR THE TREATMENT OF METABOLIC DISORDERS". Page/Page column 27. . Retrieved 2009/01/20.