704-01-8

Usage

Uses

Used in Rubber and Plastic Manufacturing Industry:
N,N,N',N'-Tetramethyl-O-phenylenediamine is used as an antioxidant for enhancing the stability and durability of rubber and plastic materials. It prevents the degradation of these materials by acting as a stabilizer against exposure to heat, light, or oxygen, thereby extending their service life and maintaining their structural integrity.
Used in Dye and Pigment Production:
TMPD is utilized as a key component in the production of dyes and pigments, contributing to the development of a wide range of colorants used in various industries, including textiles, paints, and coatings.
Used in Organic Compound Synthesis:
N,N,N',N'-Tetramethyl-O-phenylenediamine serves as an intermediate in the synthesis of various organic compounds, playing a crucial role in the chemical reactions that lead to the formation of desired products in the pharmaceutical, agrochemical, and other specialty chemical industries.

Upstream product

• 67-56-1 methanol 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 512-56-1 trimethyl phosphite 
• 95-54-5 1,2-diamino-benzene 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 64-18-6 formic acid 

Downstream Products

• 2427-09-0 2-dimethylamino-tri-N-methyl-anilinium; iodide 
• 14924-65-3 N-Formyl-N,N',N'-trimethyl-o-phenylendiamin 
• 79319-39-4 4,5-bis-(dimethylamino)phthalonitrile 
• 108486-35-7 (C₆H₄)(N(CH₃)2)2BH₂⁽¹⁺⁾*B(C₆H₅)4^(1-)={(C₆H₄)(N(CH₃)2)2BH₂}{B(C₆H₅)4} 
• 343942-84-7 1,2-dibromo-4,5-bis(dimethylamino)benzene 

Relevant academic research and scientific papers

Synthesis and Characterization of Surface-Modified Colloidal CdTe Quantum Dots

The controlled synthesis of quantized colloidal CdTe nanocrystals (in aqueous solutions) with narrow size distributions and stabilized against rapid oxidation was achieved by capping the quantum dot particles with 3-mercapto-1,2-propanediol.Nanocrystals (i.e., quantum dots) with mean diameters of 20, 25, 35, and 40 Angstroem were produced.Optical absorption spectra showed strong excitonic peaks at the smallest size; the absorption coefficient was shown to follow an inverse cube dependence on particle diameter, while the extinction coefficient per particle remained constant.The quantum yield for photoluminescence increased with decreasing particle size and reached 20percent at 20 Angstroem.The valence band edges of the CdTe quantum dots were determined by pulse radiolysis experiments (hole injection from oxidizing radicals); the bandgaps were estimated from pulse radiolysis data (redox potentials of hole and electron injecting radicals) and from the optical spectra.The dependence of the CdTe bandgap on quantum dot size was found to be much weaker than predicted by the effective mass approximation; this result is consistent with recently published theoretical calculations by several groups.

Supercritical methanol as solvent and carbon source in the catalytic conversion of 1,2-diaminobenzenes and 2-nitroanilines to benzimidazoles

Benzimidazoles and N-methylbenzimidazoles were synthesized by simply heating 1,2-diaminobenzenes in supercritical methanol over copper-doped porous metal oxides. These catalysts were derived from synthetic hydrotalcites that only contain earth-abundant starting materials. The carbon equivalents needed for the construction of the benzimidazole core originated from the solvent itself, which is known to undergo reforming to hydrogen and carbon monoxide through the formation of a formaldehyde intermediate. A variety of 1,2-diaminobenzenes were converted to the corresponding mixtures of benzimidazoles and N-methylated analogues in good yields. Interestingly, the more challenging, but readily available 2-nitroanilines, which require an additional reduction step prior to cyclization, could also be successfully converted to benzimidazoles in high selectivity. Furthermore, various other alcohols were applied besides methanol, to obtain 2-alkyl- and 1,2-dialkylbenzimidazoles. Preliminary mechanistic insights into the origins of N-alkylation as well as the reactivity of the nitro derivatives are discussed.

General catalytic methylation of amines with formic acid under mild reaction conditions

A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines including [N-13C]-labelled drugs in good to excellent yields under mild conditions. Methylation made easy: A general catalytic protocol for the methylation of amines has been developed applying, for the first time, formic acid as the C1 building block and silanes as reducing agents. A broad range of aromatic and aliphatic, both primary and secondary, amines has been converted to the corresponding tertiary amines, including [N-13C]-labelled drugs, in good to excellent yields at mild conditions (see scheme; dppp=(1,3-bis(diphenylphosphino)propane)).

A general catalytic methylation of amines using carbon dioxide

Putting CO2 to work: Carbon dioxide is shown to be a general and selective methylating reagent for secondary and primary, aromatic and aliphatic amines under reductive conditions. A variety of tertiary amines are obtained from CO2 and commercially available silanes in high yields with good tolerance to nitrile, olefin, ether, ester, and hydroxy groups. Copyright

Interactions in molecular crystals, 143 [1]. Ortho-benzene derivatives with meshed cogwheel chloromethyl and methylamino substituents: Structures and rotation enthalpy hypersurfaces

Facets of molecular dynamics in organic compounds such as coupled rotations of adjacent substituents are advantageously discussed based on structural data. Within this context, crystal structures of spatially overcrowded ortho-disubstituted benzene derivatives with chloromethyl or methylamino groups are presented together with semiempirical enthalpy hypersurfaces for the substituent rotation. Both compounds, 1-trichloromethyl-2-dichloromethyl-benzene as well as 1-trimethylammonium-2-dimethylamino-benzene exhibit comparable steric overcrowding and their preferred dynamics are predicted to be dominated by the rotation of the threefold substituted group during an approximate standstill of the twofold substituted, mirror-symmetric one. According to known solid state NMR measurements as well as to atom/atom-potential model calculations for the pentachloro ortho-xylene derivative, this molecular dynamic mode is still active in the crystal.