2-Nitro-P-phenylenediamine

Base Information

• Chemical Name: 2-Nitro-P-phenylenediamine
• CAS No.: 5307-14-2
• Deprecated CAS: 29467-01-4
• Molecular Formula: C6H7N3O2
• Molecular Weight: 226.062
• Hs Code.: 29215119
• European Community (EC) Number: 226-164-5
• ICSC Number: 1542
• NSC Number: 5377
• UN Number: 1673
• UNII: PV83F3C01Q
• DSSTox Substance ID: DTXSID4020957
• Nikkaji Number: J3.720F
• Wikidata: Q26840737
• ChEMBL ID: CHEMBL353971
• Mol file: 5307-14-2.mol

Synonyms:1,4-diamino-2-nitrobenzene;2-nitro-1,4-phenylenediamine;2-nitro-4-phenylenediamine;2-nitro-4-phenylenediamine dihydrochloride;2-nitro-4-phenylenediamine sulfate (1:1);2-nitro-p-phenylenediamine;o-nitro-p-phenylenediamine

Chemical Property of 2-Nitro-P-phenylenediamine

Chemical Property:

• Appearance/Colour: Dark red crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 135-138 °C(lit.)
• Refractive Index: 1.699
• Boiling Point: 385.4 °C at 760 mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 186.9 °C
• PSA: 97.86000
• Density: 1.446 g/cm³
• LogP: 2.44480
• Storage Temp.: Store below +30°C.
• Solubility.: 0.2g/l
• Water Solubility.: <0.1 g/100 mL at 22℃
• XLogP3: 0.5
• 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

2-Nitro-p-phenylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 43-68
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC(=C(C=C1N)[N+](=O)[O-])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.
• Description: o-Nitro-paraphenylenediamine (ONPD) is a hair dye and a sensitizer in hairdressers.
• Uses: This compound is used in hair and fur dyes. 2-Nitro-4-phenylene-diamine is a dyestuff used to dye furs brown and reddish-brown; dye intermediate in semi-permanent and permanent hair coloring products (produces brown and red shades on the hair); in different hair-dyeing preparations.

Technology Process of 2-Nitro-P-phenylenediamine

There total 27 articles about 2-Nitro-P-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: 100.0%

1-[(2-hydroxyethyl)amino]-2-nitro-4-aminobenzene (2871-01-4) → 2-nitro-1,4-phenylenediamine (5307-14-2,183870-67-9)

Guidance literature:

With ammonium hydroxide; sodium sulfite; In dimethyl sulfoxide; at 70 ℃; for 24h;

DOI:10.1016/S0040-4020(98)00181-1

Reference yield: 80.0%

1-[(2-hydroxyethyl)amino]-2-nitro-4-aminobenzene (2871-01-4) → 4-amino-2-nitrophenol (119-34-6) + 2-nitro-1,4-phenylenediamine (5307-14-2,183870-67-9)

Guidance literature:

With ammonium hydroxide; sodium sulfite; for 72h; Product distribution; Na₂SO₃ catalysis, influence of time, solvent;

DOI:10.1016/S0040-4020(98)00181-1

Reference yield: 48.0%

2,4-Dinitroanilin (97-02-9) → 2-nitro-1,4-phenylenediamine (5307-14-2,183870-67-9)

Guidance literature:

With sulfuric acid; hydrogen; platinum on activated charcoal; In acetic acid; at 85 ℃;

upstream raw materials:

nitro-p-phenylenediamine N¹-monoacetate

4-acetylamino-1-amino-2-nitrobenzene

nitro-p-phenylenediamine N¹,N⁴-diacetate

4-amino-2-nitro-benzoyl azide

Downstream raw materials:

(4-Amino-3-nitro-phenyl)-phosphoramidic acid bis-(2-chloro-ethyl) ester

1,4-bis<(p-amino-m-nitrophenyl)carboxamido>benzene

4-(3-Methylbutanoylamino)-2-nitroaniline

(R)-tert-butyl-2-[(4-amino-3-nitrophenyl)aminocarbonyl]-piperidine-1-carboxylate

Refernces

• 1、 Ghalebin, Saeed Nasiri,Bezaatpour, Abolfazl,Sadr, Moayad Hossaini,Sadjadi, Mirabdullah Seyed,Moghaddam, Mohammad Khodadadi,Szunerits, Sabine. "[1+1] Copper(II) macrocyclic Schiff base complex on rGO as a photocatalyst for reduction of nitroaromatics compounds under visible-light irradiation". . . Retrieved 2021/01/26.
• 2、 Pandarus, Valerica,Ciriminna, Rosaria,Beland, Francois,Pagliaro, Mario. "A new class of heterogeneous platinum catalysts for the chemoselective hydrogenation of nitroarenes". scheme or table. p. 1306 - 1316. Retrieved 2011/06/25.