99-98-9

Basic information

• Product Name: N,N-Dimethyl-1,4-phenylenediamine
• Synonyms: 4-ANIMODIMETHYLANILINE;4-AMINODIMETHYLANILINE;4-AMINO-N,N-DIMETHYLANILINE;4-DIMETHYLAMINOANILINE;Dimethyl-p-phenylenediamine;DIMETHYL(N,N-)-P-PHENYLENEDIAMINE;WURSTER'S RED;4-(dimethylamino)benzenamine
• CAS NO: 99-98-9
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• EINECS: 202-807-5
• Product Categories: Amines
• Mol File: 99-98-9.mol
• Article Data: 135

Chemical Properties

• Melting Point: 34-36 °C(lit.)
• Boiling Point: 262 °C(lit.)
• Flash Point: 130 °C
• Appearance: black/crystalline
• Density: 1.09
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.5914 (estimate)
• Storage Temp.: 2-8°C
• PKA: 6?+-.0.12(Predicted)
• Water Solubility: 11 g/L (20 ºC)
• Sensitive: Light Sensitive
• Stability: Stable. Incompatible with acid chlorides, acid anhydrides, strong acids, strong oxidizing agents. Combustible.
• Merck: 14,3254
• BRN: 508105
• CAS DataBase Reference: N,N-Dimethyl-1,4-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethyl-1,4-phenylenediamine(99-98-9)
• EPA Substance Registry System: N,N-Dimethyl-1,4-phenylenediamine(99-98-9)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 28-45-36/37/39-26
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: ST0874000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 99-98-9(Hazardous Substances Data)

Usage

Description

N,N-Dimethyl-1,4-phenylenediamine is an organic compound with the chemical formula C8H12N2. It is a colorless to pale yellow crystalline solid that is soluble in water and ethanol. N,N-Dimethyl-1,4-phenylenediamine is also known as N,N-Dimethyl-p-phenylenediamine and is used as a redox indicator, readily forming a stable red radical cation involved in various redox reactions.

Uses

Used in Chemical Synthesis:
N,N-Dimethyl-1,4-phenylenediamine is used as a base for the production of methylene blue, a dye with various applications in the chemical industry.
Used in Photodevelopment:
N,N-Dimethyl-1,4-phenylenediamine is used as a photodeveloper, playing a crucial role in the development of photographic films and papers.
Used in Analytical Chemistry:
N,N-Dimethyl-1,4-phenylenediamine is used as a reagent for the detection of hydrogen sulfide, a toxic gas with a characteristic rotten egg smell. It helps in identifying the presence of this gas in various environments.
Used in Cellulose Analysis:
N,N-Dimethyl-1,4-phenylenediamine is used as a reagent for cellulose, a complex carbohydrate found in plant cell walls. It aids in the analysis and characterization of cellulose in various applications.
Used in Organic Synthesis:
N,N-Dimethyl-1,4-phenylenediamine is used in organic synthesis for the preparation of various compounds, including pharmaceuticals, dyes, and other organic chemicals.
Used in Microbiology:
N,N-Dimethyl-1,4-phenylenediamine is used as a reagent for certain bacteria, helping in the identification and classification of bacterial species.
Used in Molecular Compounds Preparation:
N,N-Dimethyl-1,4-phenylenediamine may be used for the preparation of molecular compounds with tetracyano-p-quinodimethane (TCNQ). The polarized absorption spectra of these molecular compounds have been investigated, providing insights into their properties and potential applications.

Synthesis Reference(s)

Chemistry Letters, 9, p. 439, 1980Tetrahedron Letters, 34, p. 2441, 1993 DOI: 10.1016/S0040-4039(00)60436-7

Reactivity Profile

N,N-Dimethyl-1,4-phenylenediamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Incompatible with strong oxidizers, strong acids and acid anhydrides. Also incompatible with alkalis .

Hazard

Toxic by ingestion or inhalation of vapor.

Health Hazard

Lowest toxic dose with skin effect is 14 mg/kg. Irritant to skin and eyes.

Fire Hazard

When heated to decomposition, N,N-Dimethyl-1,4-phenylenediamine emits toxic fumes of nitrogen oxides.

InChI:InChI=1/C8H12N2/c1-9-7-3-5-8(10-2)6-4-7/h3-6,9-10H,1-2H3

Upstream product

• 50-00-0 formaldehyd 
• 10050-89-2 4-dimethylamino-4'-(N,N-dimethylamino)benzylideneaniline 
• 64-19-7 acetic acid 
• 62-53-3 aniline 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 123-31-9 hydroquinone 
• 74-89-5 methylamine 
• 60-11-7 methyl yellow 
• 14135-03-6 2-<(4-dimethylaminophenyl)iminomethyl>-1-methylpyridinium iodide 
• 23216-56-0 4-(N,N-dimethylamino)-N-(1-methylquinolinio-2-methylidene) aniline iodide 
• 150-74-3 4'-fluoro-4-dimethylaminoazobenzene 
• 2491-76-1 4-((4-chlorophenyl)diazenyl)-N,N-dimethylaniline 
• 3805-65-0 4-(4-bromophenylazo)-N,N-dimethylaniline 
• 3805-67-2 4-(dimethylamino)-4'-iodoazobenzene 

Downstream Products

• 27746-16-3 2-(4-(dimethylamino)phenyl)isoindoline-1,3-dione 
• 19336-90-4 N-(4-dimethylamino-phenyl)-phthalamic acid 
• 109899-82-3 N,N-dimethyl-N'-(5-nitro-[2]pyridyl)-p-phenylenediamine 
• 1749-06-0 N'-benzo[1,3]dioxol-5-ylmethylene-N,N-dimethyl-benzene-1,4-diamine 
• 82944-22-7 2-amino-N-(4-(dimethylamino)phenyl)benzamide 
• 7463-28-7 N'-acetyl-N,N-dimethyl-1,4-phenylenediamine 
• 38659-86-8 N-[4-(dimethylamino)phenyl]acetoacetamide 
• 16979-22-9 4-Chlorbenzyliden-4'-dimethylaminoanilin 
• 41001-47-2 N'-(2-chloro-benzylidene)-N,N-dimethyl-p-phenylenediamine 
• 95887-85-7 2,5-bis<<(4-dimethylamino)phenyl>amino>-3,6-dichloro-1,4-benzoquinone 
• 24776-55-4 4-[(4-Dimethylamino-phenylimino)-methyl]-phenol 
• 959-74-0 2-((4-(N,N-dimethylamino)aniline)formimidoyl)phenol 
• 13143-07-2 1-phenyl-3[4-(N,N-dimethylamino)phenyl]urea 
• 5779-20-4 1-(4-dimethylamino-phenyl)-3-phenyl-thiourea 

Relevant articles and documents

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Developments in Dynamic Covalent Chemistries from the Reaction of Thiols with Hexahydrotriazines

Dynamic covalent chemistries have garnered significant attention for their potential to revolutionize technologies in the material fields (engineering, biomedical, and sensors) and synthetic design strategies as they provide access to stimuli responsiveness and adaptive behaviors. However, only a limited number of molecular motifs have been known to display this dynamic behavior under mild conditions. Here, we identified a dynamic covalent motif - thioaminals - that is produced from the reaction of hexahydrotriazines (HTs) with thiols. Furthermore, we report on the synthesis of a new family of step-growth polymers based on this motif. The condensation efficiently proceeds to quantitative yields within a short time frame and offers versatility in functional group tolerance; thus, it can be exploited to synthesize both small molecule thioaminals as well as high molecular weight polymers from the step-growth polymerization of HTs with dithiols. Careful evaluation of substituted HTs and organic thiols supported by DFT calculations led to a chemically diverse library of polymers based on this motif. Finally, dynamic substitution reactions were employed toward the facile preparation of functional oligomers and macromolecules. This dynamic covalent motif is particularly attractive for a range of applications that include material design and drug delivery due to the economic feasibility of synthesis.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth-abundant-metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal-ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies. (Figure presented.).

Photocatalytic reduction of nitroaromatics into anilines using CeO2-TiO2 nanocomposite

The reduction of nitro compounds into amines is an important approach for synthetic and pharmaceutical chemistry. The reduced compounds are used as synthetic intermediates in the synthesis of therapeutic molecules. In the present work, we have fabricated cerium dioxide decorated TiO2 nanoparticles using a sol-gel-hydrothermal method. The synthesized nanocomposite was effectively reduced various nitro-compounds, specifically aromatic nitro compounds, into amines in visible light. All the nitro compounds screened in the photoreduction reaction showed >90% conversion with >96% selectivity. Chromatographic techniques confirmed the products obtained. The nanocomposite photocatalyst has excellent stability under the experimental condition and exhibited up to five cycles with no loss of metal content. The nanomaterials were characterized using various spectroscopic techniques.