609-20-1

Basic information

• Product Name: 2,6-DICHLORO-1,4-PHENYLENEDIAMINE
• Synonyms: 1,4-diamino-2,6-dichlorobenzene;2,6-dichloro-1,4-benzenediamine;2,6-dichloro-4-benzenediamine;2,6-dichloro-p-phenylenediamin;3,5-dichloro-1,4-phenylenediamine;c.i.37020;ci37020;daitobrownsaltrr
• CAS NO: 609-20-1
• Molecular Formula: C₆H₆Cl₂N₂
• Molecular Weight: 177.03
• EINECS: 210-184-6
• Mol File: 609-20-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 122-127 °C
• Boiling Point: 291.88°C (rough estimate)
• Flash Point: 139.3°C
• Appearance: /
• Density: 1.4668 (rough estimate)
• Vapor Pressure: 0.000762mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 3.74±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2,6-DICHLORO-1,4-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLORO-1,4-PHENYLENEDIAMINE(609-20-1)
• EPA Substance Registry System: 2,6-DICHLORO-1,4-PHENYLENEDIAMINE(609-20-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43-40-36
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: SS9175000
• Hazardous Substances Data: 609-20-1(Hazardous Substances Data)

Usage

Chemical Properties

grey powder

Uses

Different sources of media describe the Uses of 609-20-1 differently. You can refer to the following data:
1. The compound has been used as an intermediate for dyes, to some extent in preparing certain polyamide fibers, and as a curing agent for polyurethane.
2. 2,6-Dichloro-1,4-phenylenediamine is an aromatic amine that can be found in azo dyes. It was studied for potential mutagenic and toxic properties.

Production Methods

2,6-Dichloro-p-PDA is not currently produced in the United States; the sole manufacturer ceased production in 1978. It is a chemical intermediate used as a polyurethane curative, and as a monomer in the manufacture of polyamide fiber.

Preparation

The chromophore Preparation: Will 2,6-Dichioro-4-nitroaniline reduction.

General Description

Gray, microcrystalline powder or solid.

Air & Water Reactions

2,6-DICHLORO-1,4-PHENYLENEDIAMINE may be unstable to prolonged exposure to air and light. . Insoluble in water.

Reactivity Profile

2,6-DICHLORO-1,4-PHENYLENEDIAMINE neutralizes acids in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate flammable gaseous hydrogen in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When 2,6-DICHLORO-1,4-PHENYLENEDIAMINE is heated to decomposition it emits very toxic fumes of chlorine and nitrogen oxides.

Fire Hazard

Flash point data for 2,6-DICHLORO-1,4-PHENYLENEDIAMINE are not available; however, 2,6-DICHLORO-1,4-PHENYLENEDIAMINE is probably combustible.

InChI:InChI=1/C6H6Cl2N2/c7-4-1-3(9)2-5(8)6(4)10/h1-2H,9-10H2

Upstream product

• 99-30-9 4-nitro-2,6-dichloroaniline 
• 7647-01-0 hydrogenchloride 
• 100-01-6 4-nitro-aniline 
• 59992-52-8 2,6-dichloro-4-aminonitrobenzene 
• 13633-34-6 1,3-dichloro-2,5-dinitro-benzene 

Downstream Products

• 634-90-2 1,2,3,5-tetrachlorobenzene 
• 697-91-6 2,6-dichloro-1,4-benzoquinone 
• 314751-39-8 N,N'-(2,6-dichloro-p-phenylene)-bis-benzamide 
• 41946-50-3 benzoic acid-(4-amino-3,5-dichloro-anilide) 
• 6622-31-7 sulfanilic acid-(4-amino-3,5-dichloro-anilide) 
• 13908-36-6 1-(4-Amino-3,5-dichlorophenyl)-3-(2-chloroethyl)urea 
• 84562-58-3 N'-[1-(3-Bromo-4-dimethylamino-phenyl)-meth-(E)-ylidene]-2,6-dichloro-benzene-1,4-diamine 
• 84562-37-8 2,6-Dichloro-N'-[1-(3,5-dichloro-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 85103-60-2 2,6-Dichloro-N'-[1-(3-trifluoromethyl-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 84562-19-6 2,6-Dichloro-N'-[1-(2-chloro-4-dimethylamino-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 84562-49-2 2,6-Dichloro-N'-[1-(4-dimethylamino-2-methoxy-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 84562-62-9 2,6-Dichloro-N'-[1-(4-dimethylamino-2-methyl-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 84562-66-3 2,6-Dichloro-N'-[1-(4-dimethylamino-2-fluoro-phenyl)-meth-(E)-ylidene]-benzene-1,4-diamine 
• 84562-64-1 N'-[1-(2-Bromo-4-dimethylamino-phenyl)-meth-(E)-ylidene]-2,6-dichloro-benzene-1,4-diamine 

Relevant articles and documents

Cobalt-based nanoparticles prepared from MOF-carbon templates as efficient hydrogenation catalysts

The development of efficient and selective nanostructured catalysts for industrially relevant hydrogenation reactions continues to be an actual goal of chemical research. In particular, the hydrogenation of nitriles and nitroarenes is of importance for the production of primary amines, which constitute essential feedstocks and key intermediates for advanced chemicals, life science molecules and materials. Herein, we report the preparation of graphene shell encapsulated Co3O4- and Co-nanoparticles supported on carbon by the template synthesis of cobalt-terephthalic acid MOF on carbon and subsequent pyrolysis. The resulting nanoparticles create stable and reusable catalysts for selective hydrogenation of functionalized and structurally diverse aromatic, heterocyclic and aliphatic nitriles, and as well as nitro compounds to primary amines (>65 examples). The synthetic and practical utility of this novel non-noble metal-based hydrogenation protocol is demonstrated by upscaling several reactions to multigram-scale and recycling of the catalyst.

Facile protocol for reduction of nitroarenes using magnetically recoverable CoM0.2Fe1.8O4 (M = Co, Ni, Cu and Zn) ferrite nanocatalysts

Transition metal doped cobalt ferrite (CoM0.2Fe1.8O4 (M = Co, Ni, Cu, Zn)) nanoparticles were fabricated using the sol-gel methodology. The obtained ferrite nanoparticles were annealed at 400 °C and characterized using Fourier transform infra-red spectroscopy (FT-IR), X-ray diffraction (XRD), high resolution transmission electron microscopy (HR-TEM), vibrating sample magnetometry (VSM) and energy dispersive X-ray (EDX) and scanning transmission electron microscopy (STEM). In the FT-IR spectra two bands in the range 1000-400 cm-1 were observed corresponding to the M-O bond in the tetrahedral and octahedral sites. XRD patterns confirmed the formation of a cubic spinel structure with a Fd3m space-group. HR-TEM analysis revealed a quasi-spherical shape with particle sizes in the range 20-30 nm for all the synthesized ferrite nanoparticles. The lattice inter-planar distances of 0.29, 0.25, 0.21 and 0.16 nm obtained from HR-TEM corresponding to the (2 2 0), (3 1 1), (4 0 0) and (5 1 1) lattice planes respectively were in complete agreement with the XRD data. The EDX-STEM confirmed the elemental composition as per the desired stoichiometric ratio. The catalytic efficiency of the synthesized ferrite samples was explored for the reduction of nitrophenols. Cu substituted cobalt ferrite nanoparticles (CoCu0.2Fe1.8O4) possessed excellent catalytic activity while CoM0.2Fe1.8O4 (M = Co, Ni and Zn) were inactive for the same. The substrate scope of the developed protocol was also evaluated for the reduction of various CH3-, NH2-, Br-, Cl- etc. substituted nitroaromatic compounds.