m-Phenylenediamine

Base Information

• Chemical Name: m-Phenylenediamine
• CAS No.: 108-45-2
• Deprecated CAS: 1274866-89-5,1266121-34-9
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29215119
• European Community (EC) Number: 203-584-7,208-790-0,282-618-2,281-496-8
• ICSC Number: 1302
• NSC Number: 4776
• UN Number: 1673
• UNII: OE624J2447
• DSSTox Substance ID: DTXSID4021137
• Nikkaji Number: J369G
• Wikipedia: M-Phenylenediamine
• Wikidata: Q2410205
• Metabolomics Workbench ID: 53359
• ChEMBL ID: CHEMBL1595914
• Mol file: 108-45-2.mol

Synonyms:m-Phenylenediamine(8CI);1,3-Diaminobenzene;1,3-Diaminophenylene;1,3-Phenylenediamine;3-Aminoaniline;C.I. Developer 11;Developer C;Developer H;Developer M;Direct Brown BR;Direct Brown GG;NSC 4776;RT 30H;m-Aminoaniline;m-Benzenediamine;m-Diaminobenzene;N-butyl anhydride;metaphenylene diamine;1,3-Benzenediamine;

Chemical Property of m-Phenylenediamine

Chemical Property:

• Appearance/Colour: Gray to white crystal melting
• Vapor Pressure: 0.62 mm Hg ( 100 °C)
• Melting Point: 64-66 °C(lit.)
• Refractive Index: 1.6339
• Boiling Point: 283.2 °C at 760 mmHg
• PKA: 5.11, 2.50(at 20℃)
• Flash Point: 147.6 °C
• PSA: 52.04000
• Density: 1.15 g/cm³
• LogP: 2.01340
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: 350g/l
• Water Solubility.: 350 g/L (25 ºC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 64.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

1,3-Phenylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23/24/25-36-43-50/53-68-40
• Safety Statements: 28-36/37-45-60-61-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: C1=CC(=CC(=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 and skin. The substance may cause effects on the kidneys and blood. This may result in renal failure and 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 kidneys. This may result in renal failure.
• Uses: 1,3-Phenylenediamine is used in the foaming-type hair dye composition. The appearance of the high purity of the m-phenylenediamine is snow white flake solid used as a synthetic electronic grade polyimide material and epoxy resin curing agent. m-Phenylenediamine is used in the foaming-type hair dye composition. It is used as a synthetic electronic grade polyimide material and epoxy resin curing agent. It is used also block polymers, textile fibers, urethanes, petroleum additives, rubber chemicals, in corrosion inhibitors, in photography, as reagent for gold & bromine.

Technology Process of m-Phenylenediamine

There total 116 articles about m-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%

1,3-Diiodobenzene (626-00-6) → m-phenylenediamine (108-45-2,64554-26-3,76583-20-5)

Guidance literature:

With [Cu₂(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF₃COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate; In water; at 120 ℃; for 16h; chemoselective reaction; Sealed tube;

DOI:10.1016/j.catcom.2012.11.027

Reference yield: 99.0%

1-chloro-2,4-dinitro-benzene (97-00-7) → m-phenylenediamine (108-45-2,64554-26-3,76583-20-5)

Guidance literature:

With platinum on activated charcoal; hydrogen; potassium hydrogencarbonate; In methanol; at 100 ℃; for 0.0194444h; under 30003 Torr; Solvent; Reagent/catalyst; Temperature; Pressure; Catalytic behavior;

Reference yield: 97.0%

isophthalamide (1740-57-4) → m-phenylenediamine (108-45-2,64554-26-3,76583-20-5)

Guidance literature:

With sodium hypochlorite; water; at -5 - 50 ℃; for 2h; Temperature; Inert atmosphere;

upstream raw materials:

meta-dinitrobenzene

2,4-dinitrobromobenzene

1-chloro-3,5-dinitrobenzene

1,3-dibromobenzene

Downstream raw materials:

1-(3-aminophenyl)pyrrolidin-2-one

N,N'-m-phenylene-bis-propionamide

proflavine

(3-amino-phenyl)-oxalamic acid

Refernces

• 1、 Watanabe et al.. "-". . p. 1478. Retrieved 1975.
• 2、 He, Guangyu,Liu, Weifeng,Sun, Xiaoqiang,Chen, Qun,Wang, Xin,Chen, Haiqun. "Fe3O4@graphene oxide composite: A magnetically separable and efficient catalyst for the reduction of nitroarenes". . p. 1885 - 1890. Retrieved 2013.
• 3、 Baralt, Eduardo,Holy, Norman. "Hydrogenation of Nitro Compounds with an Anthranilic Acid Polymer-Bound Catalyst". . p. 2626 - 2627. Retrieved 1984.
• 4、 Ohira, Noriyuki,Aso, Yoshio,Otsubo, Tetsuo,Ogura, Fumio. "REDUCTION OF AROMATIC NITRO COMPOUNDS TO AMINES BY BENZENETELLUROL". . p. 853 - 854. Retrieved 1984.
• 5、 Ghonchepour, Ehsan,Yazdani, Elahe,Saberi, Dariush,Arefi, Marzban,Heydari, Akbar. "Preparation and characterization of copper chloride supported on citric acid-modified magnetite nanoparticles (Cu2+-CA@Fe3O4) and evaluation of its catalytic activity in the reduction of nitroarene compounds". . . Retrieved 2017.
• 6、 Desai,Swami,Hapase. "Rapid and inexpensive method for reduction of nitroarenes to anilines". . p. 1033 - 1036. Retrieved 1999.
• 7、 Sonavane, Sachin U.,Jayaram, Radha V.. "Catalytic transfer hydrogenation of nitro arenes, aldehydes, and ketones with propan-2-ol and KOH/NaOH over mixed metal oxides". . p. 843 - 849. Retrieved 2003.
• 8、 Rabinovich, I. B.,Karyakin, N. V.,Dzharimova, E. S.,Siling, S. A.,Ponomarev, I. I.,Vinogradova, S. V.. "THERMODYNAMICS OF CONDENSATION OF PHTHALONITRILE WITH m-PHENYLENEDIAMINE". . p. 716 - 723. Retrieved 1984.
• 9、 Kandathil, Vishal,Koley, Tuhin S.,Manjunatha,Dateer, Ramesh B.,Keri, Rangappa S.,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.. "A new magnetically recyclable heterogeneous palladium(II) as a green catalyst for Suzuki-Miyaura cross-coupling and reduction of nitroarenes in aqueous medium at room temperature". . p. 195 - 210. Retrieved 2018.
• 10、 Sareen, Shweta,Mutreja, Vishal,Singh, Satnam,Pal, Bonamali. "Highly dispersed Au, Ag and Cu nanoparticles in mesoporous SBA-15 for highly selective catalytic reduction of nitroaromatics". . p. 184 - 190. Retrieved 2015.