13021-15-3

Basic information

• Product Name: N,N,2,4,6-PENTAMETHYLANILINE
• Synonyms: N,N,2,4,6-PENTAMETHYLANILINE;N,N-DIMETHYLMESIDINE;Benzenamine,N,N,2,4,6-pentamethyl-;Dimethyl-(2,4,6-trimethyl-phenyl)-amine;1-(N,N-DIMETHYLAMINO)-2,4,6-TRIMETHYLBENZENE;2-DIMETHYLAMINOMESITYLENE;N,N,2,4,6-Pentamethylbenzenamine;2,4,6,N,N-Pentamethylbenzenamine
• CAS NO: 13021-15-3
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.26
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Anilines, Amides & Amines
• Mol File: 13021-15-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 46.25°C (estimate)
• Boiling Point: 213-215 °C(lit.)
• Flash Point: 174 °F
• Appearance: /
• Density: 0.907 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.159mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• PKA: 6.70±0.48(Predicted)
• CAS DataBase Reference: N,N,2,4,6-PENTAMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2,4,6-PENTAMETHYLANILINE(13021-15-3)
• EPA Substance Registry System: N,N,2,4,6-PENTAMETHYLANILINE(13021-15-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37
• RIDADR: PG3
• WGK Germany: 3
• Hazardous Substances Data: 13021-15-3(Hazardous Substances Data)

Usage

Uses

N,N,2,4,6-Pentamethylaniline was used in the synthesis of an oximino glycoside that was reduced with lithium aluminum hydride to benzyl 2-amino-2-deoxy-α-D-gluco- and -mannopyranoside hydrochloride.

General Description

N,N,2,4,6-Pentamethylaniline participates in condensation of dimeric 3,4,6-tri-O-acetyl-2-deoxy-2-nitroso-α-D-glucopyranosyl chloride with benzyl alcohol to yield an oximino glycoside.

InChI:InChI=1/C11H17N/c1-8-6-9(2)11(12(4)5)10(3)7-8/h6-7H,1-5H3

Upstream product

• 50-00-0 formaldehyd 
• 88-05-1 2,4,6-trimethylaniline 
• 74-88-4 methyl iodide 
• 7647-01-0 hydrogenchloride 
• 603-71-4 nitromesitylene 
• 64-19-7 acetic acid 
• 40751-99-3 N-oxyde de dimethylmesidine 
• 64-18-6 formic acid 
• 32884-91-6 N,N-dimethyl-O-tosylhydroxylamine 
• 108-67-8 1,3,5-trimethyl-benzene 
• 124-38-9 carbon dioxide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 155671-06-0 2,4,6,N-tetramethyl-N-nitroso-aniline 
• 86893-65-4 3-[Methyl-(2,4,6-trimethyl-phenyl)-amino]-1-phenyl-propan-1-one 
• 86893-68-7 2-{[Methyl-(2,4,6-trimethyl-phenyl)-amino]-methyl}-cyclopentanone 
• 86893-72-3 C₂₁H₂₉NO₂ 
• 250650-88-5 dimethyl-(2,4,6-trimethyl-3-nitro-phenyl)-amine 
• 527-60-6 Mesitol 
• 2819-86-5 pentamethylphenol 
• 488-71-1 2,3,4,6-tetramethylaniline 
• 88-05-1 2,4,6-trimethylaniline 
• 13021-14-2 N-methyl-2,4,6-trimethylaniline 
• 1245828-56-1 N-(dibutoxyphosphorylmethyl)-N-methyl-mesidine 
• 1245828-71-0 N,N-bis(dibutoxyphosphorylmethyl)mesidine 
• 1245828-55-0 C₁₇H₃₀NO₃P 
• 1245828-69-6 N,N-bis(diisopropoxyphosphorylmethyl)mesidine 

Relevant articles and documents

Aminomethylation of Aryl Bromides by Nickel-Catalyzed Electrochemical Redox Neutral Cross Coupling

We develop an electrochemical nickel-catalyzed aminomethylation of aryl bromides under mild conditions. The convergent paired electrolysis makes full use of anode and cathode processes, free of a terminal oxidant, a sacrificial anode, a metal reductant, and a prefunctionalized radical precursor. In addition, this method exhibits wide functional group tolerance (63 examples), including some sensitive substituents and aromatic heterocycles. This redox neutral cross coupling provides a more environmentally friendly and synthetic practical protocol for forging C(sp2)–C(sp3) bonds.

Selective formylation or methylation of amines using carbon dioxide catalysed by a rhodium perimidine-based NHC complex

Carbon dioxide can play a vital role as a sustainable feedstock for chemical synthesis. To be viable, the employed protocol should be as mild as possible. Herein we report a methodology to incorporate CO2 into primary, secondary, aromatic or alkyl amines catalysed by a Rh(i) complex bearing a perimidine-based NHC/phosphine pincer ligand. The periminide-based ligand belongs to a class of 6-membered NHC ligand accessed through chelate-assisted double C-H activation. N-Formylation and -methylation of amines were performed using a balloon of CO2, and phenylsilane as the reducing agent. Product selectivity between formylated and methylated products was tuned by changing the solvent, reaction temperature and the quantity of phenylsilane used. Medium to excellent conversions, as well as tolerance to a range of functional groups, were achieved. Stoichiometric reactions with reactants employed in catalysis and time course studies suggested that formylation and methylation reactions of interest begin with hydrosilylation of CO2 followed by reaction with amine substrates.

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.