4-Nitro-o-phenylenediamine

Base Information

• Chemical Name: 4-Nitro-o-phenylenediamine
• CAS No.: 99-56-9
• Molecular Formula: C6H7N3O2
• Molecular Weight: 153.14
• Hs Code.: 29215119
• European Community (EC) Number: 202-766-3
• UNII: 5A9AX7Y0TT
• UN Number: 1673
• ChEMBL ID: CHEMBL433721
• DSSTox Substance ID: DTXSID9020958
• ICSC Number: 1543
• Metabolomics Workbench ID: 64923
• Nikkaji Number: J3.993D
• NSC Number: 5378
• Wikidata: Q5649571
• Mol file: 99-56-9.mol

Synonyms:1,2-diamino-4-nitrobenzene;4-nitro-1,2-phenylenediamine;4-nitro-o-phenylenediamine

Chemical Property of 4-Nitro-o-phenylenediamine

Chemical Property:

• Appearance/Colour: Orange-red powder
• Vapor Pressure: 2.68E-07mmHg at 25°C
• Melting Point: 199-201 °C(lit.)
• Refractive Index: 1.708
• Boiling Point: 421.1 °C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 208.5 °C
• PSA: 97.86000
• Density: 1.446 g/cm³
• LogP: 2.44480
• Storage Temp.: Store below +30°C.
• Solubility.: 1 N HCl: ethanol, 1:1: soluble50mg/mL
• Water Solubility.: 1.2 g/L (20 ºC)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 153.053826475
• Heavy Atom Count: 11
• Complexity: 156
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Nitro-1,2-phenylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43-68-40-36/37/38-20/21/22
• Safety Statements: 36/37-45-36-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])N)N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: 4-Nitro-1,2-phenylenediamine is a hair dye constituent with potential mutagenic activity. 4-Nitro-o-phenylenediamine is used to study the in vitro activation of 4-nitro-o-phenylenediamine into a potent mutagen in Salmonella typhimurium strain TA98 4-Nitro-o-phenylenediamine was used to study the in vitro activation of 4-nitro-o-phenylenediamine into a potent mutagen in Salmonella typhimurium strain TA98 .

Technology Process of 4-Nitro-o-phenylenediamine

There total 23 articles about 4-Nitro-o-phenylenediamine 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: 99.0%

2,4-Dinitroanilin (97-02-9) → 4-Nitrophenylene-1,2-diamine (99-56-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; at 20 ℃; for 0.116667h; regioselective reaction; Sealed tube; Green chemistry;

DOI:10.1039/c5nj01492a

Reference yield: 80.0%

5-nitrobenzofuroxan (18771-86-3) → 4-Nitrophenylene-1,2-diamine (99-56-9)

Guidance literature:

With Saccharomyces cerevisiae BY; In methanol; at 20 ℃; for 6h; pH=7.0; aq. buffer; Enzymatic reaction;

DOI:10.1080/00397910802372509

Reference yield: 3.0%

2,4-Dinitroanilin (97-02-9) → 2-nitro-1,4-phenylenediamine (5307-14-2,183870-67-9) + 4-Nitrophenylene-1,2-diamine (99-56-9)

Guidance literature:

With nickel; hydrazine hydrate; In ethanol; 1,2-dichloro-ethane; at 50 - 60 ℃; for 6h;

DOI:10.1246/bcsj.56.3159

upstream raw materials:

N-(2,4-dinitrophenyl)hydroxylamine

N-(2,4-dinitrophenyl)-O-methylhydroxylamine

2,4-Dinitroanilin

ethanol

Downstream raw materials:

2,2'-((1E,1'E)-((4-nitro-1,2-phenylene)bis(azanylylidene))bis(methanylylidene))diphenol

2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole

1,2-bis(phenylsulfonylamino)-4-nitrobenzene

1-amino-2-phenylsulfonylamino-4-nitrobenzene

Refernces

• 1、 -. "ACTIVATORS OF THE RETINOIC ACID INDUCIBLE GENE "RIG-I" PATHWAY AND METHODS OF USE THEREOF". Paragraph 0438. . Retrieved 2020/03/01.
• 2、 Datta, Amitabha,Massera, Chiara,Garribba, Eugenio,Frontera, Antonio. "5,5′-Dibenzoimidazole as building block for a new 3D Co(II) coordination polymer: A combined EPR and DFT study using UB3LYP model". . p. 473 - 479. Retrieved 2019/08/26.