3171-45-7

Basic information

• Product Name: 4,6-DIMETHYL-1,2-PHENYLENEDIAMINE
• Synonyms: 4,5-dimethyl-2-benzenediamine;1,2-DIMETHYL-4,5-DIAMINOBENZENE;2-AMINO-4,5-DIMETHYLPHENYLAMINE;2-AMINO-4,5-DIMETHYLANILINE;4,5-DIAMINO-O-XYLENE;4,5-DIAMINO-1,2-DIMETHYLBENZENE;4,5-DIMETHYL-O-PHENYLENE DIAMINE;4,5-DIMETHYL-1,2-PHENYLENEDIAMINE
• CAS NO: 3171-45-7
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• EINECS: 221-635-1
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 3171-45-7.mol

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Boiling Point: 279.6 °C at 760 mmHg
• Flash Point: 144.9 °C
• Appearance: White to yellow to brownish/Crystalline Mass, Crystals or Chunks
• Density: 1.076 g/cm³
• Vapor Pressure: 0.00399mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• PKA: 5.02±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: 4,6-DIMETHYL-1,2-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIMETHYL-1,2-PHENYLENEDIAMINE(3171-45-7)
• EPA Substance Registry System: 4,6-DIMETHYL-1,2-PHENYLENEDIAMINE(3171-45-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 3171-45-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4,6-DIMETHYL-1,2-PHENYLENEDIAMINE is used as a chemical intermediate for the preparation of transition metal complexes and quinoxalinones. It plays a crucial role in the synthesis of these compounds, which have various applications in different industries.
Used in Analytical Chemistry:
4,6-DIMETHYL-1,2-PHENYLENEDIAMINE is used as a derivatizing agent for the determination of aromatic aldehydes, such as vanillin, by high performance liquid chromatography. This application allows for the accurate and sensitive detection of these compounds in various samples.
Used in Pharmaceutical Industry:
4,6-DIMETHYL-1,2-PHENYLENEDIAMINE may be used in the development of pharmaceutical compounds, given its role as a chemical intermediate in the synthesis of certain drug candidates.
Used in Research and Development:
4,6-DIMETHYL-1,2-PHENYLENEDIAMINE is utilized in research and development settings to explore its potential applications and properties, as well as to develop new methods for its synthesis and use.

Synthesis Reference(s)

Tetrahedron Letters, 42, p. 2277, 2001 DOI: 10.1016/S0040-4039(01)00163-0

InChI:InChI=1/C8H12N2/c1-5-3-7(9)8(10)4-6(5)2/h3-4H,9-10H2,1-2H3

Upstream product

• 610-23-1 4,5-dimethyl-1,2-dinitrobenzene 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 17234-76-3 4,5-dimethyl-N,N'-dibenzoyl-1,2-phenylenediamine 
• 183492-69-5 4,5-dimethyl-2-nitro-N-benzylaniline 
• 1887-60-1 5,6-dimethylbenzo-2,1,3-thiadiazole 
• 6970-77-0 N-(4,5-dimethyl-2-nitrophenyl)acetamide 
• 2198-54-1 N-(3,4-dimethylphenyl)acetamide 
• 95-64-7 4-amino-o-xylene 
• 29418-36-8 1,2-bis(3,4-dimethylphenyl)diazene 
• 1635-84-3 2,4-Dimethyl-6-nitroanilin 

Downstream Products

• 64263-00-9 5,6-dimethyl-2-(pyridin-4-yl)-1H-benzo[d]imidazole 
• 1086-80-2 lumichrome 
• 14684-48-1 1,3-dimethyllumichrome 
• 14313-45-2 5,6-dimethyl-2-phenyl-1H-benzo[d]imidazole 
• 3363-56-2 2,5,6-trimethylbenzimidazole 
• 65847-12-3 4,7,8-trimethyl-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 582-60-5 5,6-dimethyl-1H-benzo[d]imida-zole 
• 29096-75-1 2-amino-5,6-dimethylbenzimidazole 
• 102163-08-6 (1S,2S,3R)-2-(1,2,3,4-tetrahydroxybutyl)-1H-5,6-dimethylbenzimidazole 
• 70151-41-6 5,6-dimethyl-2-(p-tolyl)-1H-benzo[d]imidazole 
• 103388-08-5 N-(5,6-dimethyl-1H-benzimidazol-2-ylmethyl)-N',N'-dimethyl-N-phenyl-ethylenediamine 
• 7153-23-3 6,7-dimethylquinoxaline 
• 6957-19-3 2,3,6,7-tetramethylquinoxaline 
• 41927-06-4 2-guanidino-5,6-dimethyl-benzimidazole 

Relevant articles and documents

Some Aspects of the Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction

Some peculiar features of two most commonly used catalytic systems (Cul and CuSOVsodium ascorbate) controlling the regioselectivity of 1,3-dipolar cycloaddition of azides to terminal alkynes have been studied. Their potentialities, main disadvantages, and limitations have been demonstrated by a number of examples, including reactions of low-molecular-weight azides and alkynes containing heterocyclic substituents. The possibility of using novel reagents in click reactions is discussed.

The Direct Synthesis of Imines, Benzimidazoles and Quinoxalines from Nitroarenes and Carbonyl Compounds by Selective Nitroarene Hydrogenation Employing a Reusable Iron Catalyst

The “replacement” of noble metals by earth abundant metals is a desirable aim in catalysis and a possible way of conserving rare elements. The “replacement” is especially attractive if novel selectivity patterns are observed permitting the development of novel coupling reactions. Herein, we report on a novel, robust and reusable iron catalyst, which permits the selective hydrogenation of nitroarenes in the presence of hydrogenation-sensitive functional groups. Based on the selectivity pattern observed, the direct iron-catalyzed synthesis of imines and benzimidazoles from nitroarenes and aldehydes becomes feasible. In addition, we introduce the direct synthesis of quinoxalines from nitroarenes and diketones applying our catalyst.

A Reusable Mesoporous Nickel Nanocomposite Catalyst for the Selective Hydrogenation of Nitroarenes in the Presence of Sensitive Functional Groups

The synthesis of aromatic amines from nitroarenes through hydrogenation is an industrially and academically important reaction. In addition, the employment of base metal catalysts in reactions that are preferentially mediated by rare noble metals is a desirable aim in catalysis and an attractive element-conservation strategy. Especially appealing is the observation of novel selectivity patterns with such inexpensive metal catalysts. Herein, we report a novel mesostructured Ni nanocomposite catalyst. It is the first example of a reusable Ni catalyst that is able to hydrogenate nitroarenes selectively to anilines in the presence of highly sensitive functional groups such as C=C bonds and nitrile, aldehyde, and iodo substituents.

A O-phenylenediamine and its derivatives of the preparation method

The invention relates to a method for synthesizing organic compounds, and provides a method for preparing o-phenylenediamine and a derivative of o-phenylenediamine, for solving the problems that the process route is complex, a great amount of byproducts can be generated and are hard to purify, the reaction condition is rigorous, the environment pollution is severe and the like in a conventional method for synthesizing o-phenylenediamine derivatives. The method disclosed by the invention comprises the following steps: by taking azobenzene and a derivative of the azobenzene as raw materials, synthesizing the o-nitro azobenzene and the derivative of the o-nitro azobenzene under the coactions of a catalyst, an oxidant and a nitrating agent, and further reducing by using a reducing agent, thereby obtaining the o-phenylenediamine and the derivative of the o-phenylenediamine. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, convenient and safe, the synthesis steps are short, the purification is simple, no great waste acid pollution is caused, and the like.

A Reusable Co Catalyst for the Selective Hydrogenation of Functionalized Nitroarenes and the Direct Synthesis of Imines and Benzimidazoles from Nitroarenes and Aldehydes

The use of abundantly available transition metals in reactions that have been preferentially mediated by rare noble metals, for example, hydrogenations, is a desirable aim in catalysis and an attractive strategy for element conservation. The observation of novel selectivity patterns with such inexpensive metal catalysts is especially appealing. Herein, we report a novel, robust, and reusable cobalt catalyst that permits the selective hydrogenation of nitroarenes in the presence of highly hydrogenation-sensitive functional groups, as well as the direct synthesis of imines from nitroarenes and aldehydes or ketones in the presence of such substituents. Furthermore, we introduce the first base-metal-mediated direct synthesis of benzimidazoles from nitroarenes and aldehydes. Functional groups that are easy to hydrogenate are again well tolerated.

Palladium nanoparticles supported on nitrogen-functionalized active carbon: A stable and highly efficient catalyst for the selective hydrogenation of nitroarenes

Nitrogen-functionalized active carbon-supported ultrasmall Pd nanoparticles were conveniently prepared by using a postloading method. The Pd catalyst was highly active and selective for the hydrogenation of nitroarenes at room temperature under ambient pressure. Reducible groups such as ketone, carboxylic acid, and ester were not hydrogenated, and the corresponding anilines were obtained quantitatively. The Pd catalyst demonstrated high stability and could be reused 10 times without the loss of catalytic performance. Be active, be fit! A facile method to prepare nitrogen-functionalized active carbon (NAC) has been described. The small-sized Pd nanoparticles are supported on NAC by using a postloading method. The representative catalyst Pd@NAC-800 demonstrated high activity and selectivity for the selective hydrogenation of nitroarenes under mild reaction conditions.

Synthesis of riboflavines, quinoxalinones and benzodiazepines through chemoselective flow based hydrogenations

Robust chemical routes towards valuable bioactive entities such as riboflavines, quinoxalinones and benzodiazepines are described. These make use of modern flow hydrogenation protocols enabling the chemoselective reduction of nitro group containing building blocks in order to rapidly generate the desired amine intermediates in situ. In order to exploit the benefits of continuous processing the individual steps were transformed into a telescoped flow process delivering selected benzodiazepine products on scales of 50 mmol and 120 mmol respectively.

Combined Pd/C and montmorillonite catalysis for one-pot synthesis of benzimidazoles

A series of nineteen benzimidazoles were prepared from ortho-nitroanilines by one-pot transfer hydrogenation, condensation, and dehydrogenation enabled by the concurrent use of two heterogeneous catalysts: montmorillonite-K10 and Pd/C. This strategy was further employed to accomplish a five-step, three-component synthesis of an antifungal benzimidazoquinazoline by using a simple one-pot procedure.

DERIVATIVES OF PHENAZINE USEFUL TO TREAT CANCER

The present invention relates to derivatives of phenazine having a general formula (I) for use as an agent for treating cancer.

Efficient method for the synthesis of benzimidazoquinazoline derivatives with three-point diversity

An efficient strategy for the preparation of a novel heterocyclic ring system of benzimidazoquinazolines with three-point diversity has been described. The compounds were obtained by treating o-phenylene diamines with o-nitrobenzaldehyde to give benzimidazoles, followed by reduction of the nitro group to give an amine. Derivatization of the resulting amine with isothiocyanates followed by in situ cyclodesulfurization at rt furnished the title compounds in high yields and purities. Copyright Taylor & Francis Group, LLC.