17327-77-4

Basic information

• Product Name: N,N,2,5-tetramethylaniline
• Synonyms: benzenamine, N,N,2,5-tetramethyl-; N,N,2,5-Tetramethylaniline
• CAS NO: 17327-77-4
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.2328
• Mol File: 17327-77-4.mol

Chemical Properties

• Boiling Point: 215.748°C at 760 mmHg
• Flash Point: 86.091°C
• Density: 0.933g/cm³
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: N,N,2,5-tetramethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2,5-tetramethylaniline(17327-77-4)
• EPA Substance Registry System: N,N,2,5-tetramethylaniline(17327-77-4)

Safety Data

• Hazardous Substances Data: 17327-77-4(Hazardous Substances Data)

Upstream product

• 95-72-7 2-chloro-1,4-dimethyl-benzene 
• 124-40-3 dimethyl amine 
• 496837-65-1 2,5-dimethylphenyl methanesulfonate 
• 67-56-1 methanol 
• 95-78-3 2,5-Dimethylaniline 
• 64-18-6 formic acid 
• 50-00-0 formaldehyd 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 

Relevant articles and documents

Light-promoted N,N-dimethylation of amine and nitro compound with methanol catalyzed by Pd/TiO2 at room temperature

A series of TiO2 supported nano-Pd catalysts (Pd/TiO2) were prepared and used for the N,N-dimethylation of different amines and nitro compounds with methanol under UV irradiation at room temperature. A wide range of N,N-dimethyl amines were one-pot synthesized with up to 98% by applying aliphatic secondary amines, aromatic primary amines, aliphatic primary amines and aromatic nitro compounds as starting materials. It is noteworthy that up to 90% yield of 4-chloro-N,N-dimethylaniline was obtained by adjusting the Pd loadings on the TiO2 and the dehalogenation reaction was inhibited. Finally, a reaction mechanism is discussed, involving PhN = CH2 and PhNHCH3 as reaction intermediates.

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)).

Addressing challenges in palladium-catalyzed cross-couplings of aryl mesylates: Monoarylation of ketones and primary alkyl amines

Mor(DalPhos) for Me(sylates): Described are the first examples of ketone mono-α-arylation and primary aliphatic amine monoarylation employing aryl methanesulfonate coupling partners. A range of functionalized aryl mesylates were employed with dialkyl ketones, and also with primary and secondary amines as well as the otherwise challenging coupling partners acetone and methylamine. Ad=adamantyl. Copyright

Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine

Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L1Pd(0).