3478-91-9

Basic information

• Product Name: N,N-dimethyl-2-(2-nitrophenyl)ethanamine
• CAS NO: 3478-91-9
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.2304
• Mol File: 3478-91-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 279.9°C at 760 mmHg
• Flash Point: 123.1°C
• Density: 1.113g/cm³
• Vapor Pressure: 0.00392mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: N,N-dimethyl-2-(2-nitrophenyl)ethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-2-(2-nitrophenyl)ethanamine(3478-91-9)
• EPA Substance Registry System: N,N-dimethyl-2-(2-nitrophenyl)ethanamine(3478-91-9)

Safety Data

• Hazardous Substances Data: 3478-91-9(Hazardous Substances Data)

Usage

General Description

N,N-dimethyl-2-(2-nitrophenyl)ethanamine, also known as dimethyl-2-nitrophenethylamine, is a chemical compound with the molecular formula C10H14N2O2. It is a derivative of amphetamine and possesses a nitro group attached to a phenyl ring, as well as two methyl groups attached to the nitrogen atom. N,N-dimethyl-2-(2-nitrophenyl)ethanamine is known to have psychoactive and stimulant effects on the central nervous system, making it a potential candidate for use in the development of various pharmaceutical drugs. However, its use is also associated with potential neurotoxicity and other adverse effects, and it is classified as a controlled substance in some jurisdictions. Overall, N,N-dimethyl-2-(2-nitrophenyl)ethanamine is a chemical of interest for its pharmacological properties, but also one that requires careful consideration and regulation due to its potential risks.

Synthetic route

(2-nitrobenzyl)dimethyl<(trimethylsilyl)methyl>ammonium bromide → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
With cesium fluoride In N,N,N,N,N,N-hexamethylphosphoric triamide for 24h; Ambient temperature; Yield given;

(2-bromoethyl)-2-nitrobenzene (16793-89-8) + dimethyl amine (124-40-3) → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
In ethanol

formaldehyd (50-00-0) + 2-nitro-β-phenethylamine hydrochloride → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
at 135℃;

bromhydric acid + 2-nitro-benzeneethanol (15121-84-3) → dimethyl-(2-nitro-phenethyl)-amine (3478-91-9)

Conditions	Yield
With dimethyl amine In ethanol

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) → (2-amino-phenethyl)-dimethyl-amine (3478-92-0)

Conditions	Yield
aluminum nickel In methanol	89%
(catalytic hydrogenation);

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9) → trimethyl-(2-nitro-phenethyl)-ammonium; picrate

Conditions	Yield
With benzene

dimethyl-(2-nitro-phenethyl)-amine (3478-91-9) → N-Cinnamoyl-2-<2-dimethylamino-ethyl>-anilin (3478-82-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (catalytic hydrogenation) 2: CHCl3 View Scheme

Upstream product

• 15121-84-3 2-nitro-benzeneethanol 
• 50-00-0 formaldehyd 
• 16793-89-8 (2-bromoethyl)-2-nitrobenzene 
• 124-40-3 dimethyl amine 

Downstream Products

• 3478-82-8 N-Cinnamoyl-2-<2-dimethylamino-ethyl>-anilin 
• 3478-92-0 (2-amino-phenethyl)-dimethyl-amine 

Relevant articles and documents

Rearrangement of (Substituted benzyl)trimethylammonium Ylides in a Nonbasic Medium: The Improved Sommelet-Hauser Rearrangement

Benzyl quaternary ammonium ylide formation in a nonbasic medium was accomplished by fluoride anion induced desilylation of benzyldimethylammonium bromide (3a) and ortho- or para-substituted benzyl analogues 3b-k.Treatment of 3 with CsF in HMPA at room temperature gives high yields of the Sommelet-Hauser rearrangement products 7 from 3a and methyl-, acetoxy-, and chloro-substituted analogues 3b-f.However, formation of the Stevens rearrangement products 8 is competitive for the reaction of compounds 3g-k having strong electron-withdrawing substituents such as acetyl, cyano, and nitrogen groups.From the o-cyano-substituted analogue 3h, a considerable amount of para Sommelet-Hauser rearrangement product is isolated.

Serotonin inhibitors. 3. Compounds related to 2'-(3-dimethylaminopropylthio)cinnamanilide.

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