4-Nitrobenzene-1,3-diol

Base Information

• Chemical Name: 4-Nitrobenzene-1,3-diol
• CAS No.: 3163-07-3
• Molecular Formula: C6H5NO4
• Molecular Weight: 155.11
• Hs Code.: 2908999090
• European Community (EC) Number: 221-616-8
• UNII: H7ZWK9J803
• DSSTox Substance ID: DTXSID60185509
• Nikkaji Number: J217.319K
• Wikidata: Q27279740
• Metabolomics Workbench ID: 38825
• Mol file: 3163-07-3.mol

Synonyms:4-nitrobenzene-1,3-diol;3163-07-3;4-Nitroresorcinol;1,3-Benzenediol, 4-nitro-;2,4-Dihydroxy-nitrophenol;4-nitro-1,3-benzenediol;H7ZWK9J803;3-bromo-4-(methylthio)nitrobenzene;MFCD04117945;2,4 dihydroxy nitrophenol;3-Hydroxy-4-nitrophenol;UNII-H7ZWK9J803;SCHEMBL68980;DTXSID60185509;CHEBI:173661;EINECS 221-616-8;AKOS000277597;AM803683;AS-57896;SY109272;BB 0262198;CS-0036812;EN300-50105;AB01002650-01;A919625;AE-562/43461488;J-018498;Q27279740;Z336080410

Chemical Property of 4-Nitrobenzene-1,3-diol

Chemical Property:

• Vapor Pressure: 1.84E-05mmHg at 25°C
• Melting Point: 122 °C
• Refractive Index: 1.667
• Boiling Point: 352.8 °C at 760 mmHg
• PKA: 7.17±0.13(Predicted)
• Flash Point: 166.1 °C
• PSA: 86.28000
• Density: 1.58g/cm³
• LogP: 1.52920
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 8.13g/L(24.70 oC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 155.02185764
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99%, ^*data from raw suppliers

4-Nitroresorcinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1O)O)[N+](=O)[O-]
• Uses: 4-Nitroresorcinol is used as a reagent in the synthesis of Deguelin (D229205); a compound that exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers.

Technology Process of 4-Nitrobenzene-1,3-diol

There total 37 articles about 4-Nitrobenzene-1,3-diol 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: 97.0%

recorcinol (108-46-3) → 4-nitroresorcinol (3163-07-3)

Guidance literature:

With zirconyl nitrate; In acetone; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2006.02.057

Reference yield: 93.0%

5-fluoro-2-nitrophenol (446-36-6) → 4-nitroresorcinol (3163-07-3)

Guidance literature:

With water; potassium hydroxide; at 90 - 100 ℃; for 43h;

Reference yield: 93.0%

nitrobenzene (98-95-3,26969-40-4) → 4-nitroresorcinol (3163-07-3)

Guidance literature:

With dihydrogen peroxide; copper(II) nitrate; In phosphate buffer; acetonitrile; at 50 ℃;

DOI:10.1080/00304940009355937

upstream raw materials:

benzoate d'hydroxy-3 phenyle

4-nitroso-1,3-benzenediol

2,4-diaminonitrobenzene

2,4-dihydroxy-5-nitrobenzoic acid

Downstream raw materials:

4-nitro-2-phenylazo-resorcinol

4-nitro-6-phenylazo-resorcinol

2,4-dichloro-6-nitro-resorcinol

4-chloro-6-nitro-resorcinol

Refernces

• 1、 MacHida, Shiori,Kida, Motoki,Muramatsu, Satoru,Hirao, Takehiro,Haino, Takeharu,Inokuchi, Yoshiya. "Gas-Phase UV Spectroscopy of Chemical Intermediates Produced in Solution: Oxidation Reactions of Phenylhydrazines by DDQ". . p. 6697 - 6702. Retrieved 2021.
• 2、 Schmitt, Robert J.,Ross, David S.,Hardee, John R.,Wolfe, James F.. "Synthesis of 4,6-Dinitroresorcinol". . p. 5568 - 5569. Retrieved 1988.
• 3、 Manna, Srimanta,Karmakar, Parthasarathi,Ali, Syed Samim,Guria, Uday Narayan,Sarkar, Ripon,Datta, Pallab,Mandal, Debasish,Mahapatra, Ajit Kumar. "A Michael addition-cyclization-based switch-on fluorescent chemodosimeter for cysteine and its application in live cell imaging". supporting information. p. 4951 - 4958. Retrieved 2018/04/03.