229486-99-1

Basic information

• Product Name: N-(2,5-dimethoxybenzyl)-N-methylamine
• Synonyms: N-(2,5-dimethoxybenzyl)-N-methylamine;2,5-DIMETHOXY-N-METHYLBENZENEMETHANAMINE;OTAVA-BB 1268277;[(2,5-dimethoxyphenyl)methyl](methyl)amine
• CAS NO: 229486-99-1
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.234
• Mol File: 229486-99-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2,5-dimethoxybenzyl)-N-methylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,5-dimethoxybenzyl)-N-methylamine(229486-99-1)
• EPA Substance Registry System: N-(2,5-dimethoxybenzyl)-N-methylamine(229486-99-1)

Safety Data

• Hazardous Substances Data: 229486-99-1(Hazardous Substances Data)

Usage

Uses

N-(2,5-dimethoxybenzyl)-N-methylamine is used as a reagent in the chemical industry for the stereoselective synthesis of trans-?2-?substituted-?cyclopropylamines from α-?chloroaldehydes. This application is significant because it allows for the creation of specific isomers with desired properties, which can be crucial in the development of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
N-(2,5-dimethoxybenzyl)-N-methylamine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its ability to participate in stereoselective reactions makes it a valuable tool in the synthesis of drugs with specific therapeutic properties, potentially leading to more effective treatments for a range of medical conditions.
Used in Chemical Research:
In the field of chemical research, N-(2,5-dimethoxybenzyl)-N-methylamine serves as a key compound for exploring new reaction pathways and understanding the mechanisms behind various chemical processes. Its unique structure and reactivity make it an interesting subject for study, which can contribute to the advancement of organic chemistry and related disciplines.

Upstream product

• 593-51-1 methylamine hydrochloride 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 114943-72-5 [1-(2,5-Dimethoxy-phenyl)-meth-(Z)-ylidene]-methyl-amine 

Downstream Products

• 1079173-32-2 C₂₁H₂₃FN₄O₃ 
• 302899-95-2 3-benzyloxycarbonylamino-N-(3,6-dioxo-cyclohexa-1,4-dienylmethyl)-N-methyl-succinamic acid methyl ester 
• 229487-04-1 (3S)-methyl 3-amino-4-butanoate 
• 475273-36-0 N-(2,5-dimethoxyphenyl)methyl-N-methyl-cis-3-phenylsulfanylacrylamide 
• 229487-02-9 3-benzyloxycarbonylamino-N-(2,5-dimethoxy-benzyl)-N-methyl-succinamic acid methyl ester 

Relevant articles and documents

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic cosolvent.

Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-ones

In this work, we further investigated a previously introduced class of cholinesterase inhibitors. The removal of the carbamic function from the lead compound xanthostigmine led to a reversible cholinesterase inhibitors 3. Some new 3-[ω-(benzylmethylamino)alkoxy]xanthen-9-one analogs were designed, synthesized, and evaluated for their inhibitory activity against both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The length of the alkoxy chain of compound 3 was increased and different substituents were introduced. From the IC50 values, it clearly appears that the carbamic residue is crucial to obtain highly potent AChE inhibitors. On the other hand, peculiarity of these compounds is the high selectivity toward BuChE with respect to AChE, being compound 12 the most selective one (6000-fold). The development of selective BuChE inhibitors may be of great interest to clarify the physiological role of this enzyme and to provide novel therapeutics for various diseases.

An alternative synthesis of a potent GPIIb/IIIa receptor antagonist

A key intermediate to SB-214857 was prepared via an oxidative cyclization of a hydroquinone with a flanking aspartate side chain using Fremy's salt.