4913-13-7

Basic information

• Product Name: N,N,3,5-TETRAMETHYLANILINE
• Synonyms: 3,5-Xylidine, N,N-dimethyl-;n,n,3,5-tetramethyl-benzenamin;N,N-3,5-Tetramethylbenzenamine;N,N-Dimethyl-sym-m-xylidine;N,N-DIMETHYL-SYM-XYLIDENE;N,N,3,5-TETRAMETHYLANILINE;N,N-DIMETHYL-3,5-DIMETHYLANILINE;N,N-DIMETHYL-3,5-XYLIDINE
• CAS NO: 4913-13-7
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 225-539-0
• Mol File: 4913-13-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 1.08°C (estimate)
• Boiling Point: 226-228 °C(lit.)
• Flash Point: 195 °F
• Appearance: clear yellow to orange liquid
• Density: 0.913 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0794mmHg at 25°C
• Refractive Index: n20/D 1.544(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.37±0.19(Predicted)
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 1933736
• CAS DataBase Reference: N,N,3,5-TETRAMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,3,5-TETRAMETHYLANILINE(4913-13-7)
• EPA Substance Registry System: N,N,3,5-TETRAMETHYLANILINE(4913-13-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-33-36/37/38
• Safety Statements: 26-36
• RIDADR: 2810
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4913-13-7(Hazardous Substances Data)

Usage

Description

N,N,3,5-Tetramethylaniline, also known as 3,5,N,N-Tetramethylaniline, is a clear yellow to orange liquid with unique chemical properties. It is an organic compound that has been utilized in various applications due to its specific characteristics.

Uses

Used in Chemical Synthesis:
N,N,3,5-Tetramethylaniline is used as a catalyst in the polymeric synthesis of glycol methacrylate. Its presence accelerates the reaction, leading to more efficient and faster production of the desired polymer.
Used in Rapid Quenching:
N,N,3,5-Tetramethylaniline is employed in the rapid quenching of 1,8-dihydroxyanthraquinone (DHAQ). This process is crucial in the production of certain chemicals and materials, where the compound's ability to quickly quench DHAQ contributes to the overall efficiency and effectiveness of the reaction.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its use as a catalyst in chemical synthesis, N,N,3,5-Tetramethylaniline could potentially be utilized in the pharmaceutical industry for the production of various drugs and medicinal compounds. Its role in facilitating reactions and improving the synthesis process can be beneficial in creating new and improved pharmaceutical products.
Used in Chemical Research:
N,N,3,5-Tetramethylaniline's unique properties also make it a valuable compound for research purposes. It can be used in various experiments and studies to better understand its behavior and potential applications in different fields, including materials science, environmental science, and more.

InChI:InChI=1/C10H15N/c1-8-5-9(2)7-10(6-8)11(3)4/h5-7H,1-4H3

Upstream product

• 99-12-7 5-nitro-m-xylene 
• 13330-20-6 N,N,N,3,5-pentamethylbenzenaminium iodide 
• 60-29-7 diethyl ether 
• 940-93-2 2,4,6-trimethylpyrylium chlorate(VII) 
• 124-40-3 dimethyl amine 
• 50-00-0 formaldehyd 
• 108-69-0 3,5-dimethylaminoaniline 
• 773-01-3 2,4,6-trimethylpyrylium tetrafluoroborate 
• 613-48-9 N,N-diethyl-p-toluidine 
• 2217-07-4 N,N-dipropylaniline 
• 99-97-8 Dimethyl-p-toluidine 
• 91-67-8 N,N-diethyl-m-toluidine 
• 74-88-4 methyl iodide 
• 1247014-57-8 C₁₀H₁₅NO 

Downstream Products

• 110529-76-5 4,4'-bis-dimethylamino-2,6,2',6'-tetramethyl-benzophenone 
• 110530-04-6 2,4'-bis-dimethylamino-4,6,2',6'-tetramethyl-benzophenone 
• 69432-31-1 C₃₂H₃₆N₈ 
• 613-48-9 N,N-diethyl-p-toluidine 
• 99-97-8 Dimethyl-p-toluidine 
• 91-67-8 N,N-diethyl-m-toluidine 
• 2217-07-4 N,N-dipropylaniline 
• 92115-02-1 [3,5-Dimethyl-4-(4-nitro-phenylazo)-phenyl]-dimethyl-amine 
• 4980-19-2 4‐(dimethylamino)‐2,6‐dimethylbenzaldehyde 
• 14275-09-3 4-bromo-3,5-dimethyl-N,N-dimethylaniline 
• 29785-94-2 2,6-dimethyl-4-dimethylamino(nitroso)benzene 

Relevant articles and documents

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction

A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.

Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and α-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols. Anilines can be coupled with aldimines or aldehydes in a visible-light-mediated photoredox-catalyzed process. Reductive single electron transfer (SET) umpolung of the carbonyl derivatives leads to the generation of intermediary ketyl and α-amino radical anions, which were used for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.