14814-75-6

Usage

Uses

Used in Chemical Industry:
N1,N3-DiMethylbenzene-1,3-diaMine is used as a precursor in the synthesis of various dyes, pigments, and polymers for [application reason] its ability to contribute to the color and stability of these products.
Used in Dye and Pigment Production:
N1,N3-DiMethylbenzene-1,3-diaMine is used as a key component in the formulation of dyes and pigments for [application reason] its capacity to enhance the color intensity and durability of these substances in various applications, such as textiles, plastics, and printing inks.
Used in Polymer Industry:
N1,N3-DiMethylbenzene-1,3-diaMine is used as a monomer or intermediate in the production of polymers for [application reason] its role in creating specific polymer properties, such as improved strength, flexibility, or resistance to environmental factors.

Upstream product

• 64-18-6 formic acid 
• 50617-73-7 N-methyl-m-phenylenediamine 
• 108-45-2 m-phenylenediamine 
• 59255-77-5 tert-butyl N-(3-{[(tert-butoxy)carbonyl]amino}phenyl)carbamate 
• 67-56-1 methanol 
• 7006-52-2 3-chloro-N-methylaniline 
• 74-89-5 methylamine 
• 25227-79-6 N,N'-1,3-diaminobenzene-bis-formamide 
• 917-54-4 methyllithium 

Downstream Products

• 95995-03-2 N,N'-dimethyl-2,4,6,N,N'-pentanitro-m-phenylenediamine 
• 16349-49-8 1,3,1',3'-tetramethyl-1,1'-m-phenylene-bis-thiourea 
• 51021-23-9 1,3-bis(N-methylacetamido)benzene 
• 1338604-76-4 C₂₀H₁₈N₄O₂ 
• 1404300-75-9 N₁-(acridin-9-yl)-N₁,N₃-dimethylbenzene-1,3-diamine 
• 1589587-87-0 C₂₂H₂₆N₄ 
• 1263375-90-1 C₂₂H₁₈I₂N₂O₂ 
• 154576-86-0 N,N'-diallyl-N,N'-dimethyl-1,3-benzenediamine 

Relevant academic research and scientific papers

NON-COORDINATING ANION TYPE ACTIVATORS FOR USE WITH POLYOLEFIN POLYMERIZATION CATALYSTS

The present disclosure is related to activator compounds represented by: [Ar(E11R11R22H)xx(E22R33R44)yy][QR55R66R77R88]zz In the formula Ar is a C66-C3030 aromatic hydrocarbyl group, provided that if Ar is a multicyclic ring, then each E11 and each E22 are substitutions on a single ring. Also, x is 1 to 4; y is 0 to 3; z = x; and x+y is 2 to 6. Each of E11 and E22 are independently selected from nitrogen or phosphorous and Q is selected from group 13 of the Periodic Table of the Elements. Additionally, each of R11, R22, R33 and R44 are independently selected from C11-C4040 aliphatic hydrocarbyl, substituted C11-C4040 aliphatic hydrocarbyl and each of R55, R66, R77, and R88 is independently a C66-C2424 hydrocarbyl or a C66-C2424 substituted hydrocarbyl. The present disclosure also relates to catalyst systems including a catalyst and the activator compound. Also, the present disclosure relates to methods of polymerizing olefins.

Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source

Methanol can be employed as a green and sustainable methylating agent to form C-C and C-N bonds via borrowing hydrogen (BH) methodology. Herein we explored the activity of the acridine-derived SNS-Ru pincer for the activation of methanol to apply it as a C1 building block in different reactions. Our catalytic system shows great success toward the β-C(sp3)-methylation reaction of 2-phenylethanols to provide good to excellent yields of the methylated products. We investigated the mechanistic details, kinetic progress, and temperature-dependent product distribution, which revealed the slow and steady generation of in situ formed aldehyde, is the key factor to get the higher yield of the β-methylated product. To establish the environmental benefit of this reaction, green chemistry metrics are calculated. Furthermore, dimerization of 2-naphthol via methylene linkage and formation of N-methylation of amine are also described in this study, which offers a wide range of substrate scope with a good to excellent yield.

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.

Facile synthesis and antitumor activity of novel N(9) methylated AHMA analogs

A facile synthesis of novel antitumor N(9)-methyl-3-(9-acridinylamino)-5- hydroxymethylaniline (AHMA) derivatives is described. Boc protection of aminobenzoic acids followed by LiAlH4 reduction yielded novel methylaminobenzyl alcohol reactants. Their interaction with 9-chloroacridine provides N(9)-methylated AHMA derivatives for biological screening. A preliminary anti-proliferative assay against seven cancer cell lines identified compounds with low μM IC50 values. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

The iridium-catalyzed synthesis of symmetrically and unsymmetrically alkylated diamines under mild reaction conditions

An iridium catalyst - stabilized by an anionic P,N ligand - was used for the symmetrical and unsymmetrical monoalkylation of para-, meta-, and ortho-benzenediamines. Benzyl and aliphatic alcohols were used as alkylating reagents. 28 derivatives were synthesized. 14 of them are new compounds. Furthermore, the alkylation of the pharmacological important diamine Dapson (dapsone) is described. 14 dapsone derivatives were synthesized among them 9 new compounds. Copyright

Rational and predictable chemoselective synthesis of oligoamines via Buchwald-Hartwig amination of (hetero)aryl chlorides employing Mor-Dalphos

We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl) morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl] 2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl] 2/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a′) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)] + fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH2CH 2CH2(4-C6H4NH2)] +OTf- (7) in 72% yield.

Acid-induced conformational alteration of cis-preferential aromatic amides bearing N-methyl-N-(2-pyridyl) moiety

A series of cis-preferential aromatic N-methyl amides was designed and synthesized, and acid-induced conformational alteration of these compounds was investigated by means of NMR measurements in solution and X-ray crystal structure analysis. Compounds with a terminal N-methyl-N-(2-pyridyl) amide unit showed acid-induced conformational change from cis to trans, while those with a terminal N-methyl-2-pyridinecarboxamide unit showed a change of the carbonyl orientation from anti to syn with retention of cis conformation.

A general procedure to selectively prepare N-alkylanilines by an unexpected reaction of (Z)-(tert-butylsulfanyl)(aryl)diazenes with alkyllithium reagents

A general procedure has been set up to prepare, selectively, the N-monoalkylanilines 7, reacting (Z)-(tert-butylsulfanyl)(aryl)diazenes 3 with alkyllithium 6 (MeLi, BuLi, s-BuLi, n-C6H13Li). The reactions were carried out in anhydrous diethyl ether at 0°C or - 78°C, depending on the reagent 6, and then at room temperature. In optimal conditions the yields of the pure products 7 (uncontaminated by dialkylation products) were from good to excellent: for 38 considered examples, 34 were positive with yields varying between 61percent and 91percent (average yield 78percent). Collateral proofs were carried out to support a hypothesized reaction mechanism.