4-(4-Nitrophenylazo)resorcinol

Base Information

• Chemical Name: 4-(4-Nitrophenylazo)resorcinol
• CAS No.: 74-39-5
• Deprecated CAS: 123502-51-2,1888411-20-8
• Molecular Formula: C12H9N3O4
• Molecular Weight: 259.221
• Hs Code.: 29270000
• European Community (EC) Number: 200-808-5
• NSC Number: 3914
• UNII: YND5ZT5BS3
• DSSTox Substance ID: DTXSID30861621
• Nikkaji Number: J3.038.596I,J5.260D
• Wikipedia: Azo_violet
• Wikidata: Q4676694
• Metabolomics Workbench ID: 64862
• ChEMBL ID: CHEMBL1604790
• Mol file: 74-39-5.mol

Synonyms:azoviolet

Chemical Property of 4-(4-Nitrophenylazo)resorcinol

Chemical Property:

• Appearance/Colour: dark red to brown crystalline powder
• Vapor Pressure: 3.98E-09mmHg at 25°C
• Melting Point: 195-200 °C (dec.)(lit.)
• Refractive Index: 1.665
• Boiling Point: 509.2 °C at 760 mmHg
• PKA: 8.05±0.35(Predicted)
• Flash Point: 261.7 °C
• PSA: 111.00000
• Density: 1.45 g/cm³
• LogP: 3.94460
• Storage Temp.: Store below +30°C.
• Water Solubility.: Soluble in dilute sodium hydroxide. Insoluble in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 259.05930578
• Heavy Atom Count: 19
• Complexity: 336

Purity/Quality:

99% ^*data from raw suppliers

AzoViolet ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Azo Dyes
• Canonical SMILES: C1=CC(=CC=C1N=NC2=C(C=C(C=C2)O)O)[N+](=O)[O-]
• Description: Oxygen violet can be prepared by one-step reaction of p-nitroaniline and 1,3-benzenediol. Azo violet can be used to prepare an azobenzene photochromic liquid crystal compound. Photochromic liquid crystal compounds have both photochromic properties and liquid crystallinity, which has become a research hotspot in the field of information storage. Azobenzene-based liquid crystals are the most interesting photochromic liquid crystal materials in recent years due to their unique photoinduced cis-trans isomerism. Azobenzene compounds undergo reversible cis-trans isomerization under the action of light, which makes them have great potential applications in many aspects such as optical storage, photo-holography and optical information processing.
• Uses: 4-(4-Nitrophenyl)azoresorcinol is used for the detection of magnesium with which it yields a bright blue color in alkaline solution and it also used to determine molybdenum with which it forms a red-violet complex: Nikitina, Andrianova, C.A. 75, 136789v (1971). It is a derivitized resorcinol dye compound with an absorption maximum of 432 nm. Used as a pH indicator.

Technology Process of 4-(4-Nitrophenylazo)resorcinol

There total 8 articles about 4-(4-Nitrophenylazo)resorcinol 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: 98.0%

4-nitro-aniline (100-01-6,104810-17-5) + recorcinol (108-46-3) → 4-(p-nitrophenylazo)resorcinol (74-39-5)

Guidance literature:

4-nitro-aniline; With hydrogenchloride; In water; at 0 - 20 ℃; for 0.0833333h;

recorcinol; In water; at 0 - 5 ℃; for 0.166667h;

DOI:10.1016/j.dyepig.2015.02.007

Reference yield: 90.0%

4-nitrobenzenediazonium chloride (100-05-0) + recorcinol (108-46-3) → 4-(p-nitrophenylazo)resorcinol (74-39-5)

Guidance literature:

With sodium hydroxide; In water; for 0.366667h;

DOI:10.1016/j.dyepig.2011.09.013

Reference yield:

4-aminoresorcinol (13066-95-0) + 4-nitro-aniline (100-01-6,104810-17-5) → 4-(p-nitrophenylazo)resorcinol (74-39-5)

Guidance literature:

4-nitro-aniline; With hydrogenchloride; In water; at 70 ℃;

With sodium nitrite; In water; at 0 - 5 ℃;

4-aminoresorcinol; With acetic acid; at 10 ℃; for 0.416667h; pH=5 - 6;

DOI:10.21608/EJCHEM.2020.23484.2427

upstream raw materials:

4-nitrobenzenediazonium chloride

recorcinol

(E)-4-nitro-benzenediazo hydroxide; sodium-salt

4-nitro-aniline

Downstream raw materials:

[2,4-Bis-(4,6-dichloro-[1,3,5]triazin-2-yloxy)-phenyl]-(4-nitro-phenyl)-diazene

2,4-di-(2’-hydroxyethoxy)-5-nitro-4'-nitroazobenzene

C₃₄H₂₁N₃O₁₄

2,4-di-(2’-hydroxyethoxy)-4'-nitroazobenzene

Refernces

• 1、 Augustine, Asiagwu K.,Otutu, Johnson O.. "Synthesis of nitroso-based bis-azo dyes and their dyeing properties for polyethylene terephthalate and polyamide". . p. 3949 - 3959. Retrieved 2020/11/18.
• 2、 Koukabi, Nadiya,Otokesh, Somayeh,Kolvari, Eskandar,Amoozadeh, Ali. "Convenient and rapid diazotization and diazo coupling reaction via aryl diazonium nanomagnetic sulfate under solvent-free conditions at room temperature". . p. 12 - 17. Retrieved 2015/10/05.