o-PHENYLENEDIAMINE

Base Information

• Chemical Name: o-PHENYLENEDIAMINE
• CAS No.: 95-54-5
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29215119
• European Community (EC) Number: 202-430-6
• ICSC Number: 1441
• NSC Number: 5354
• UN Number: 1673
• UNII: 8B713N8Q0F
• DSSTox Substance ID: DTXSID3025881
• Nikkaji Number: J3.954C
• Wikipedia: O-Phenylenediamine
• Wikidata: Q3596763
• Metabolomics Workbench ID: 54911
• ChEMBL ID: CHEMBL70582
• Mol file: 95-54-5.mol

Synonyms:1,2-diaminobenzene;1,2-diaminobenzene dihydrochloride;1,2-phenylenediamine;2,3-diaminobenzene;o-phenylenediamine;ortho-phenylenediamine;orthophenylenediamine

Chemical Property of o-PHENYLENEDIAMINE

Chemical Property:

• Appearance/Colour: brown yellow, red brown or brown crystals
• Vapor Pressure: 0.01 mm Hg ( 25 °C)
• Melting Point: 99-102 °C
• Refractive Index: 1.66
• Boiling Point: 257 °C at 760 mmHg
• PKA: 4.46(at 25℃)
• Flash Point: 124.9 °C
• PSA: 52.04000
• Density: 1.15 g/cm³
• LogP: 2.01340
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: H2O: 1 tablet/10 mL, clear, colorless
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 62.9
• Transport DOT Label: Poison

Purity/Quality:

99%(min) ^*data from raw suppliers

1,2-Phenylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 20/21-25-36-40-43-50/53-68
• Safety Statements: 28-36/37-45-60-61-1/2

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC=C(C(=C1)N)N
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance is mildly irritating to the skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in anaemia. This substance is possibly carcinogenic to humans.
• Uses: 1. It can be used as a cationic dye intermediates, being the main raw material of pesticides, carbendazim and other fungicides. 2. It can be used as analytical reagent, fluorescent indicator, also used in organic and dye synthesis. It can be used as pesticides, pharmaceuticals and dyes intermediates 3.? As a pesticide intermediates, dye intermediates phenylenediamine is the intermediate of fungicide carbendazim, methyl thiophanate, and thiabendazole, but also insecticides quinalphos intermediates. In addition, it can also used as an important intermediate of dye industry. 4. The goods are intermediates of dyes, pesticides, additives and photographic materials. Itself is the dye fur yellow brown M. It can be used in the manufacture of polyamide, polyurethane, fungicides carbendazim and thiophanate, reduction scarlet GG, leveling agent, antioxidant MB, also used in the preparation of the developer, surfactant and so on. 5.? It can be used as intermediates of chemical raw materials, pesticides and dyes. m-Phenylenediamine is used in the manu facture of a variety of dyes, in hair dyeformulations, as a rubber curing agent, inpetroleum additives, as a photographic developing agent, and as an analytical reagent. o-Phenylenediamine is used as an intermediate in the manufacture of dyes, pigments, andfungicides. It is also used in hair dye formulation, as a photographic developing agent,and in organic synthesis. o-Phenylenediamine is an amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list. It is actively involved in the preparation of pharmaceuticals by reacting substituted o-phenylenediamine with various diketones.
• Production method: Take o-nitroaniline as raw materials, use sodium sulfide reduction or catalytic hydrogenation for reduction of o-phenylenediamine. Addition of 21% sodium sulfide solution and o-nitroaniline into the reducing pot, raising the temperature to 90 °C, close and raise the temperature to 105-110 °C and increase the pressure to 0.1-0.2 MPa, stirring and reducing for 5 h, cooling to below 40 °C, filter. The filter cake is heated and melted, vacuum distillation, collecting the fraction in 140-210 °C (7.89kPa), namely o-phenylenediamine with the yield of 70-80%. The hydrogenation process should proceed in the autoclave with the reaction temperature of 95-105 °C with the pressure of about 2MPa. It should be subject to hydrogenation reaction under the action of nickel catalyst for about 1h until the hydrogen pressure does not decline. The yield of o-phenylenediamine was above 97%. There are several preparation methods as follows. O-Nitroaniline and Sodium Sulfide Reduction Its reaction with o-nitroaniline and sodium sulfide solution at a pressure of 98 to 196 kPa and a reaction temperature of 105 to 110 ° C, being also carried out at a reaction temperature of 120 to 130 °C under atmospheric pressure for 3 to 4 hours to obtain o-benzenediamine amine. O-nitroaniline: hydrogenation reduction method Use o-nitroaniline as the raw material and Raney nickel as the catalyst, the reaction temperature was raised from 95 to 105 ° C in the autoclave, and the product was obtained by stirring at 1.960 MPa under continuous pressure of hydrogen gas until the pressure did not drop. For the above two preparation methods, the sodium sulfide reduction method can obtain the product of high purity with relative mature process. There are more factories in the domestic production of o-phenylenediamine. But the method has poor labor protection conditions with much wastewater. There are still some problems in the catalytic hydrogenation with industrialization needs to be further improved. In addition, there is also o-dichlorobenzene ammonia solution, there are more units have been studied, but not yet industrialized.

Technology Process of o-PHENYLENEDIAMINE

There total 234 articles about 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: 78.0%

1,2-Dinitrobenzene (528-29-0) → 2-nitro-aniline (88-74-4) + 1,2-diamino-benzene (95-54-5)

Guidance literature:

1,2-Dinitrobenzene; With sodium tetrahydroborate; In water; at 20 ℃; for 0.25h; Inert atmosphere; Green chemistry;

In water; at 20 ℃; for 0.75h; Inert atmosphere; Green chemistry;

DOI:10.1039/c2gc35917k

Reference yield: 47.0%

2,3-diethynylquinoxaline (91-19-0) + edaravone (89-25-8) → 1,1,2,2-tetrakis(5-methyl-3-oxo-2-phenyl-1,2-dihydro-3H-pyrazol-4-yl)ethane + 1,2-diamino-benzene (95-54-5) + 4,4-methine-bis-(3-methyl-1-phenyl-2-pyrazolin-5-one) (61466-03-3,4174-09-8,1388851-19-1)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; at 20 - 25 ℃; for 48h;

DOI:10.1016/j.mencom.2012.01.014

Reference yield: 40.0%

1-(2-nitrophenyl)aminobenzimidazole (185012-08-2) → benzoimidazole (51-17-2,79351-71-6) + 1,2-diamino-benzene (95-54-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 40 ℃; for 3.5h;

DOI:10.1007/BF02256841

upstream raw materials:

o-benzoquinone-1,2-dioxime

N-benzylidene-o-phenylenediamine

2-[(Ethoxycarbonyl)amino]aniline

N¹-(2-aminophenyl)-N²-phenylurea

Downstream raw materials:

2-((2-hydroxyethyl)amino)aniline

N-(2-mercapto-ethyl)-1,2-benzenediamine

4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

2-(2'-pyridyl)benzimidazole

Refernces

• 1、 Henwood, Adam F.,Antón-García, Daniel,Morin, Mégane,Rota Martir, Diego,Cordes, David B.,Casey, Colin,Slawin, Alexandra M. Z.,Lebl, Tomas,Bühl, Michael,Zysman-Colman, Eli. "Conjugated, rigidified bibenzimidazole ancillary ligands for enhanced photoluminescence quantum yields of orange/red-emitting iridium(iii) complexes". . p. 9639 - 9653. Retrieved 2019.
• 2、 Arora, Aayushi,Oswal, Preeti,Singh, Siddhant,Nautiyal, Divyanshu,Rao, Gyandshwar K.,Kumar, Sushil,Singh, Ajai K.,Kumar, Arun. "Organoselenium ligand-stabilized copper nanoparticles: Development of a magnetically separable catalytic system for efficient, room temperature and aqueous phase reduction of nitroarenes". . . Retrieved 2021.
• 3、 Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju. "Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines". supporting information. p. 1915 - 1923. Retrieved 2021/02/06.
• 4、 Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.. "Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines". . p. 9355 - 9360. Retrieved 2021/07/19.