702-24-9

Basic information

• Product Name: N-(4-Methoxybenzyl)-N-methylamine
• Synonyms: AKOS BC-0897;(4-METHOXY-BENZYL)-METHYL-AMINE;4-METHOXY-N-METHYLBENZYLAMINE;N-(4-METHOXYBENZYL)-N-METHYLAMINE;N-Methyl-4-methoxybenzylamine;4-METHOXY-N-METHYLBENZYLAMINE 95%;(4-methoxyphenyl)-N-methylmethanamine;1-(4-methoxyphenyl)-N-methylmethanamine
• CAS NO: 702-24-9
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• EINECS: 200-002-4
• Product Categories: Amines and Anilines
• Mol File: 702-24-9.mol
• Article Data: 51

Chemical Properties

• Melting Point: 238 °C
• Boiling Point: 88 °C
• Flash Point: 109℃
• Appearance: colorless liquid.
• Density: 1.008 g/mL at 25 °C
• Vapor Pressure: 0.104mmHg at 25°C
• Refractive Index: n20/D1.529
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.14±0.10(Predicted)
• CAS DataBase Reference: N-(4-Methoxybenzyl)-N-methylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Methoxybenzyl)-N-methylamine(702-24-9)
• EPA Substance Registry System: N-(4-Methoxybenzyl)-N-methylamine(702-24-9)

Safety Data

• Hazard Codes: C,Xn
• Statements: 36/37/38-34-22
• Safety Statements: 26-36/37/39
• RIDADR: UN 2735 8/PG III
• WGK Germany: 1
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 702-24-9(Hazardous Substances Data)

Usage

Uses

N-(4-Methoxybenzyl)-N-methylamine is used in the synthetic preparation of many types of compounds, including the synthesis of trifluoromethyl-sulfonimidamides from sulfinamides as well as the preparation of piperazinylquinazoline amine compounds as toll-like receptor 9 signaling antagonists for treatment of immune disorders.

InChI:InChI=1/C9H13NO/c1-10-7-8-3-5-9(11-2)6-4-8/h3-6,10H,7H2,1-2H3/p+1

Upstream product

• 2746-25-0 p-Methoxybenzyl bromide 
• 74-89-5 methylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 13114-23-3 4-methoxybenzyl-N-methylimine 
• 67-56-1 methanol 
• 70978-37-9 1-(azidomethyl)-4-methoxybenzene 
• 32872-35-8 N-methyl-p-methoxythiobenzamide 
• 2393-23-9 4-methoxy-benzylamine 
• 50-00-0 formaldehyd 
• 333-27-7 methyl trifluoromethanesulfonate 
• 100-66-3 methoxybenzene 
• 105-13-5 4-Methoxybenzyl alcohol 
• 616-38-6 carbonic acid dimethyl ester 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 110932-36-0 (4-methoxy-benzyl)-methyl-[1]naphthylmethyl-amine 
• 128942-59-6 2-[(4-Methoxy-benzyl)-methyl-amino]-1-phenyl-ethanone 
• 109250-32-0 3-[N-methyl-N-(4-methoxybenzyl)]aminopropiophenone hydrochloride 
• 909187-43-5 N-(4-methoxybenzyl)-6-fluoro-N-methylpyridin-2-amine 
• 1135433-86-1 C₁₃H₁₅ClN₄O 
• 213840-40-5 N,N'-bis-(4-methoxy-benzyl)-N,N'-dimethyl-2,6-bis-(3-triisopropylsilanyloxy-propoxy)-pyrimido[5,4-d]pyrimidine-4,8-diamine 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Novel 3-Aminomethylindole Derivatives as Potential Multifunctional Anti-Inflammatory and Neurotrophic Agents

The development of multifunctional molecules that are able to simultaneously interact with several pathological components has been considered as a solution to treat the complex pathologies of neurodegenerative diseases. Herein, a series of aminomethylindole derivatives were synthesized, and evaluation of their application for antineuroinflammation and promoting neurite outgrowth was disclosed. Our initial screening showed that most of the compounds potently inhibited lipopolysaccharide (LPS)-stimulated production of NO in microglial cells and potentiated the action of NGF to promote neurite outgrowth of PC12 cells. Interestingly, with outstanding NO/TNF-α production inhibition and neurite outgrowth-promoting activities, compounds 8c and 8g were capable of rescuing cells after injury by H2O2. Their antineuroinflammatory effects were associated with the downregulation of the LPS-induced expression of the inflammatory mediators inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Western blotting and immunofluorescence assay results indicated that the mechanism of their antineuroinflammatory actions involved suppression of the MAPK/NF-κB signal pathways. Further studies revealed that another important reason for the high comprehensive antineuroinflammatory activity was the anti-COX-2 capabilities of the compounds. All these results suggest that the potential biochemical multifunctional profiles of the aminomethylindole derivatives provide a new sight for the treatment of neurodegenerative diseases.

A Next Generation Synthesis of BACE1 Inhibitor Verubecestat (MK-8931)

The development of a commercial manufacturing route to verubecestat (MK-8931) is described, highlights of which include the application of a continuous processing step to outcompete fast proton transfer in a Mannich-type ketimine addition, a copper-cataly

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.