3,4-Dihydroxy-5-nitrobenzaldehyde

Base Information

• Chemical Name: 3,4-Dihydroxy-5-nitrobenzaldehyde
• CAS No.: 116313-85-0
• Molecular Formula: C7H5NO5
• Molecular Weight: 183.12
• Hs Code.: 2913000090
• European Community (EC) Number: 441-810-8,601-421-8
• UNII: 34J6743XV2
• DSSTox Substance ID: DTXSID60151345
• Nikkaji Number: J472.275B
• Wikidata: Q72494658
• ChEMBL ID: CHEMBL1244
• Mol file: 116313-85-0.mol

Synonyms:3,4-dihydroxy-5-nitrobenzaldehyde;DHNB compound

Chemical Property of 3,4-Dihydroxy-5-nitrobenzaldehyde

Chemical Property:

• Appearance/Colour: yellow color crystalline powder.
• Vapor Pressure: 0.000319mmHg at 25°C
• Melting Point: 147 °C
• Refractive Index: 1.718
• Boiling Point: 310.9 °C at 760 mmHg
• PKA: 4.78±0.38(Predicted)
• Flash Point: 141.1 °C
• PSA: 103.35000
• Density: 1.667 g/cm³
• LogP: 1.34170
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 183.01677226
• Heavy Atom Count: 13
• Complexity: 213

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36-43
• Safety Statements: 26-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1[N+](=O)[O-])O)O)C=O
• Uses: 3,4-Dihydroxy-5-nitrobenzaldehyde (Entacapone EP Impurity C) is an Entacapone (E558500) impurity. Entacapone (E558500) impurity.

Technology Process of 3,4-Dihydroxy-5-nitrobenzaldehyde

There total 5 articles about 3,4-Dihydroxy-5-nitrobenzaldehyde 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%

isonitrovanillin (6635-20-7) → 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0)

Guidance literature:

With hydrogen bromide; acetic acid; In water; at 110 ℃; for 39h;

DOI:10.1021/acs.jmedchem.7b01438

Reference yield:

isonitrovanillin (6635-20-7) + pyrographite (7440-44-0) → 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0)

Guidance literature:

With acetic acid; In conc. hydrobromic acid; water;

Reference yield:

vanillin (121-33-5,8014-42-4) → 3,4-dihydroxy-5-nitrobenzaldehyde (116313-85-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; mixture of gaseous nitrogen oxides

2: fuming hydrochloric acid / 140 °C

With hydrogenchloride; diethyl ether; mixture of gaseous nitrogen oxides;

upstream raw materials:

isonitrovanillin

vanillin

pyrographite

isovanillin

Downstream raw materials:

3-benzyloxy-4-hydroxy-5-nitro-benzaldehyde

2-Cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide

3-Nitro-5-[2-(4-pyridyl)vinyl] catechol

N-Isopropyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)acrylamide

Refernces

• 1、 Rancati, Fabio,Bromidge, Steven M.,Del Sordo, Simone,La Rosa, Salvatore,Parini, Carlo,Gagliardi, Stefania. "Synthesis of 7-substituted-(2,3-dihydro-1,4-benzodioxin-5-yl)-piperazine". . p. 2507 - 2520. Retrieved 2008.
• 2、 Kurane, Rajanikant,Gaikwad, Vipul,Jadhav, Jagannath,Salunkhe, Rajashri,Rashinkar, Gajanan. "Ferrocene tagged functional polymer: A robust solid-phase reagent for O-demethylation". . p. 6361 - 6366,6. Retrieved 2012.
• 3、 Selvam, Chelliah,Lemasson, Isabelle A.,Brabet, Isabelle,Oueslati, Nadia,Karaman, Berin,Cabaye, Alexandre,Tora, Amélie S.,Commare, Bruno,Courtiol, Tiphanie,Cesarini, Sara,McCort-Tranchepain, Isabelle,Rigault, Delphine,Mony, Laetitia,Bessiron, Thomas,McLean, Heather,Leroux, Frédéric R.,Colobert, Fran?oise,Daniel, Hervé,Goupil-Lamy, Anne,Bertrand, Hugues-Olivier,Goudet, Cyril,Pin, Jean-Philippe,Acher, Francine C.. "Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites". supporting information. p. 1969 - 1989. Retrieved 2018/03/21.