3,4-Dihydroxy-5-nitrobenzoic Acid

Base Information

• Chemical Name: 3,4-Dihydroxy-5-nitrobenzoic Acid
• CAS No.: 84211-30-3
• Molecular Formula: C7H5NO6
• Molecular Weight: 199.12
• ChEMBL ID: CHEMBL170549
• DSSTox Substance ID: DTXSID30560445
• Nikkaji Number: J472.277I
• Wikidata: Q82443834
• Mol file: 84211-30-3.mol

Synonyms:3,4-Dihydroxy-5-nitrobenzoic Acid;84211-30-3;Benzoic acid, 3,4-dihydroxy-5-nitro-;CHEMBL170549;MFCD00872080;SCHEMBL644782;DTXSID30560445;HDPSONAKHMNQPA-UHFFFAOYSA-N;3,4-Dihydroxy-5-nitrobenzoicAcid;3,4-dihydroxy-5-nit-robenzoic acid;3,4-Dihydroxy-5-nitro-benzoic acid;BDBM50017858;AKOS016347771;AS-76649;SY326969;CS-0157757;A864162

Chemical Property of 3,4-Dihydroxy-5-nitrobenzoic Acid

Chemical Property:

• Vapor Pressure: 1.7E-07mmHg at 25°C
• Melting Point: >222oC (dec.)
• Boiling Point: 411.1oC at 760 mmHg
• Flash Point: 188oC
• PSA: 123.58000
• Density: 1.799g/cm3
• LogP: 1.22740
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 199.01168688
• Heavy Atom Count: 14
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

3,4-Dihydroxy-5-nitrobenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1[N+](=O)[O-])O)O)C(=O)O
• Uses: 3,4-Dihydroxy-5-nitrobenzoic Acid is a useful synthetic intermediate in the synthesis of Entacapone; a peripherally selective inhibitor of catechol-O-methyltransferase (COMT). Also an antiparkinsonian. 3,4-Dihydroxy-5-nitrobenzoic Acid is a useful synthetic intermediate in the synthesis of Entacapone (E558500); a peripherally selective inhibitor of catechol-O-methyltransferase (COMT). Also an antiparkinsonian.

Technology Process of 3,4-Dihydroxy-5-nitrobenzoic Acid

There total 4 articles about 3,4-Dihydroxy-5-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: 100.0%

3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0) → 3,4-dihydroxy-5-nitrobenzoic acid (84211-30-3)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; dimethyl sulfoxide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.3390/molecules26195964

Reference yield: 95.0%

5-nitrovanillic acid (15785-54-3) → 3,4-dihydroxy-5-nitrobenzoic acid (84211-30-3)

Guidance literature:

With water; hydrogen bromide; acetic acid; at 120 ℃; for 3.5h;

DOI:10.1021/jm1001524

Reference yield: 45.0%

4-hydroxy-3-methoxy-5-nitrobenzoic acid methyl ester (42590-00-1) → 3,4-dihydroxy-5-nitrobenzoic acid (84211-30-3)

Guidance literature:

With hydrogen bromide; In water; Reflux;

DOI:10.1002/cmdc.201402298

upstream raw materials:

5-nitrovanillic acid

4-hydroxy-3-methoxybenzoic acid methyl ester

4-hydroxy-3-methoxy-5-nitrobenzoic acid methyl ester

3,4-dihydroxy-5-nitrobenzaldehyde

Downstream raw materials:

3,4-diacetoxy-5-nitrobenzoic acid

butyl 3,4-dihydroxy-5-nitrobenzoate

methyl 3,4-dihydroxy-5-nitro-benzoate

3-Benzyloxy-4-iodo-5-nitroso-benzoic acid methyl ester

Refernces

• 1、 -. "DUOCARMYCIN ANALOGUES". Page/Page column 57. . Retrieved 2020/08/22.
• 2、 -. "Small Molecule Xanthine Oxidase Inhibitors and Methods of Use". Paragraph 0083-0084. . Retrieved 2014/06/24.