73902-65-5

Basic information

• Product Name: N2,3-DIMETHYL-1,2-BENZENEDIAMINE
• Synonyms: N2,3-DIMETHYL-1,2-BENZENEDIAMINE;N1,6-Dimethylbenzene-1,2-diamine
• CAS NO: 73902-65-5
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.197
• Mol File: 73902-65-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N2,3-DIMETHYL-1,2-BENZENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N2,3-DIMETHYL-1,2-BENZENEDIAMINE(73902-65-5)
• EPA Substance Registry System: N2,3-DIMETHYL-1,2-BENZENEDIAMINE(73902-65-5)

Safety Data

• Hazardous Substances Data: 73902-65-5(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
N2,3-DIMETHYL-1,2-BENZENEDIAMINE is used as a monomer in the production of synthetic polymers for various applications, such as in the manufacturing of plastics and rubber. Its presence in the polymerization process contributes to the formation of polymers with specific properties, enhancing their performance in different industries.
Used in Dye Production:
N2,3-DIMETHYL-1,2-BENZENEDIAMINE is used as a key intermediate in the production of dyes, particularly in the synthesis of pigments and other colorants. Its chemical structure allows for the creation of dyes with unique color characteristics, making it valuable in the dye industry.
Used in Cosmetic Formulation:
N2,3-DIMETHYL-1,2-BENZENEDIAMINE is used as an ingredient in the formulation of hair dyes and other cosmetic products. Its chemical properties enable it to act as a color developer or a stabilizer, contributing to the effectiveness and longevity of the color in hair dyes.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N2,3-DIMETHYL-1,2-BENZENEDIAMINE may also be used in the pharmaceutical industry as an intermediate in the synthesis of various drugs, due to its chemical reactivity and the presence of amino groups that can be further modified or functionalized.

Upstream product

• 437-86-5 2-fluoro-3-nitrotoluene 
• 108-44-1 1-amino-3-methylbenzene 
• 3970-40-9 2-chloro-3-nitrotoluene 
• 70254-74-9 2,N-dimethyl-6-nitro-aniline 

Downstream Products

• 17583-45-8 1,7-dimethyl-1H-benzo[d]imidazole 
• 945021-49-8 C₉H₁₁N₃ 
• 1191924-14-7 C₂₂H₁₉Cl₂N₅ 
• 126990-86-1 1,8-Dimethyl-1,4-dihydro-quinoxaline-2,3-dione 

Relevant articles and documents

Cu-Catalyzed C-H Allylation of Benzimidazoles with Allenes

CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.

Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines

The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.

Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions.

Bicyclic Benzimidazole Compounds and Their Use as Metabotropic Glutamate Receptor Potentiators

Compounds of Formula I: wherein A, B, D, L, R1, R2, R3, R4, m, and n are as defined for Formula I in the description. The invention also relates to processes for the preparation of the compounds and to new intermediates employed in the preparation, pharmaceutical compositions containing the compounds, and to the use of the compounds in therapy.

Discovery of small molecule benzimidazole antagonists of the chemokine receptor CXCR3

High-throughput screening identified a low molecular weight antagonist of CXCR3 displaying micromolar activity in a membrane filtration-binding assay. Systematic modification of the benzimidazole core and tethered acetophenone moiety established tractable SAR of analogs with improved physicochemical properties and sub-micromolar activity across both human and murine receptors.

Linear free energy substitutent effect on flavin redox chemistry

A systematic study on the effect of various substituents at the 7- and/or 8-position on the redox properties of isoalloxazines (flavins) is reported. The redox properties of these flavin derivatives were studied by cyclic voltammetry in 100 mM, pH 7.4 HEPES and 200 mM, pH 10 borate buffers. The magnitude and direction of the effect was dependent on the nature and location of the substituent. The redox potentials of the substituted flavins were correlated with the Hammett σ value of the substituents.