704-01-8

Basic information

• Product Name: N,N,N',N'-TETRAMETHYL-O-PHENYLENEDIAMINE
• Synonyms: N,N,N',N'-TETRAMETHYL-O-PHENYLENEDIAMINE;1,2-bis(dimethylamino)benzene;N,N,N',N'-Tetramethyl-1,2-benzenediamine;n,n,n’,n’-tetramethyl-2-benzenediamine;n,n,n’,n’-tetramethyl-o-phenylenediamin;o-Phenylenebis(dimethylamine);o-Phenylenediamine, N,N,N',N'-tetramethyl-;N,N,N',N'-tetramethylbenzene-1,2-diamine
• CAS NO: 704-01-8
• Molecular Formula: C₁₀H₁₆N₂
• Molecular Weight: 164.25
• EINECS: 211-878-1
• Mol File: 704-01-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 8.9°C
• Boiling Point: 281.73°C (rough estimate)
• Appearance: /
• Density: 0.9560
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: N,N,N',N'-TETRAMETHYL-O-PHENYLENEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-TETRAMETHYL-O-PHENYLENEDIAMINE(704-01-8)
• EPA Substance Registry System: N,N,N',N'-TETRAMETHYL-O-PHENYLENEDIAMINE(704-01-8)

Safety Data

• Hazardous Substances Data: 704-01-8(Hazardous Substances Data)

Usage

General Description

N,N,N',N'-Tetramethyl-O-phenylenediamine, also known as TMPD, is a chemical compound commonly used as an antioxidant in rubber and plastic manufacturing processes. It is a colorless to pale yellow liquid with a strong amine odor and is highly soluble in water. TMPD functions as a stabilizer, preventing the degradation of materials due to exposure to heat, light, or oxygen. It is also used in the production of dyes and pigments, as well as in the synthesis of organic compounds. The compound is considered to have low acute toxicity, but prolonged or repeated exposure may cause irritation to the skin, eyes, and respiratory system. Therefore, appropriate safety measures should be taken when handling N,N,N',N'-Tetramethyl-O-phenylenediamine.

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 
• 64-18-6 formic acid 
• 95-83-0 4-Chloro-1,2-phenylenediamine 

Downstream Products

• 2427-09-0 2-dimethylamino-tri-N-methyl-anilinium; iodide 
• 14924-65-3 N-Formyl-N,N',N'-trimethyl-o-phenylendiamin 
• 343942-84-7 1,2-dibromo-4,5-bis(dimethylamino)benzene 
• 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} 

Relevant articles and documents

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.

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)).

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.