14367-46-5

Basic information

• Product Name: N-ethyl-p-methoxy-alpha-methylphenethylamine
• Synonyms: N-ethyl-p-methoxy-alpha-methylphenethylamine;2-(Ethylamino)-1-(4-Methoxyphenyl)-Prophane;2-(Ethylamino)-1-(4-methoxyphenyl)-propane;BENZENETHANAMINE, N-ETHYL- 4-METHOXY-ALPHA-METHYL;2-Ethylamino-1-(p-methoxyphenyl)propane;N-Ethyl-1-(4-methoxyphenyl)propane-2-amine;N-Ethyl-2-(4-methoxyphenyl)-1-methylethylamine;N-Ethyl-4-methoxy-α-methylbenzeneethanamine
• CAS NO: 14367-46-5
• Molecular Formula: C₁₂H₁₉NO
• Molecular Weight: 193.28536
• EINECS: 238-339-3
• Product Categories: Chemical and pharmaceutical intermediates;pharmaceutical intermediates
• Mol File: 14367-46-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 280.6 °C at 760 mmHg
• Flash Point: 116.1 °C
• Appearance: /
• Density: 0.943 g/cm³
• Vapor Pressure: 0.00374mmHg at 25°C
• Refractive Index: 1.496
• Water Solubility: 1.984g/L at 25℃
• CAS DataBase Reference: N-ethyl-p-methoxy-alpha-methylphenethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-ethyl-p-methoxy-alpha-methylphenethylamine(14367-46-5)
• EPA Substance Registry System: N-ethyl-p-methoxy-alpha-methylphenethylamine(14367-46-5)

Safety Data

• Hazardous Substances Data: 14367-46-5(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H19NO/c1-4-13-10(2)9-11-5-7-12(14-3)8-6-11/h5-8,10,13H,4,9H2,1-3H3

Synthetic route

1-methoxy-4-(prop-1-yn-1-yl)benzene (2749-94-2) + ethylamine (75-04-7) → Ethyl-[1-(4-methoxy-phenyl)-propyl]-amine (40023-81-2) + N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
Stage #1: 1-methoxy-4-(prop-1-yn-1-yl)benzene; ethylamine; Ind2TiMe2 In toluene at 105℃; under 760 Torr; for 7h; Stage #2: With sodium cyanoborohydride; zinc(II) chloride In methanol; toluene at 25℃; for 16h;	A n/a B 77%

diethyl sulfate (64-67-5) + benzylidene-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-amine → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
at 160 - 170℃;

N-ethyl-N-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-formamide → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
With hydrogenchloride

4-methoxybenzyl methyl ketone (122-84-9) + ethylamine (75-04-7) → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
With ethanol; water; aluminium

2-amino-1-(4-methyoxyphenyl)propane (64-13-1) + acetaldehyde (75-07-0) → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
With ethanol; sodium acetate; nickel Hydrogenation;

4-Methoxyphenylacetic acid (104-01-8) → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate 2: water; aluminium; ethanol View Scheme

E-1-(4'-methoxyphenyl)prop-1-ene (4180-23-8) → N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; aqueous H2O2 / beim Erhitzen des Reaktionsprodukts mit wss. H2SO4 2: water; aluminium; ethanol View Scheme

N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5) → 4-Hydroxy-Phenethylamine (69389-96-4)

Conditions	Yield
With hydrogen bromide
With CYP2D6 In phosphate buffer at 37℃; for 2h; Enzyme kinetics; Demethylation; Enzymatic reaction;
With hydrogen bromide

N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5) + ethyl iodide (75-03-6) → N,N-diethyl-1-methyl-2-(p-methoxyphenyl)ethylamine (195213-66-2)

(2S)-3-(4-carboxymethoxy-phenyl)-2-methoxy-propionic acid ethyl ester (638189-59-0) + N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5) → (2S)-3-[4-({ethyl-[2-(4-methoxy-phenyl)-1-methyl-ethyl]-carbamoyl}-methoxy)-phenyl]-2-methoxy-propionic acid

N-ethyl-p-methoxy-a-methyl-Phenethylamine (14367-46-5) → 5-[n-ethyl-[1-methyl-2-(4-methoxyphenyl)]-ethylamino]-1-pentane carboxylic acid ethylester (57646-55-6)

Conditions	Yield
With hydrogenchloride; sodium iodide; triethylamine In water; butanone

Upstream product

• 64-67-5 diethyl sulfate 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 104-01-8 4-Methoxyphenylacetic acid 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 75-04-7 ethylamine 
• 2749-94-2 1-methoxy-4-(prop-1-yn-1-yl)benzene 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 75-07-0 acetaldehyde 

Downstream Products

• 69389-96-4 4-Hydroxy-Phenethylamine 
• 57646-55-6 5-[n-ethyl-[1-methyl-2-(4-methoxyphenyl)]-ethylamino]-1-pentane carboxylic acid ethylester 

Relevant articles and documents

Ind2TiMe2-catalyzed addition of methyl- and ethylamine to alkynes

We describe a very simple hydrogenation-like experimental protocol for the addition of gaseous methyl- and ethylamine to alkynes in the presence of Ind2TiMe2 as the catalyst. For efficient hydroamination reactions it is sufficient to stir a mixture of the alkyne and the catalyst in toluene at temperatures between 80°C (terminal alkynes) and 105°C (internal alkynes) under a constant pressure of 1 atm of the corresponding amine. After subsequent reduction of the initially formed imines, methyl- and ethylamine derivatives are the final products of the described one-pot reaction sequences. In the case of 2-alkyl-1-phenylalkynes as starting materials, biologically interesting 2-phenylethylamine derivatives possessing a small methyl or ethyl substituent at the N atom are easily accessible by the new reaction protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.