943-17-9

Basic information

• Product Name: Etilefrine hydrochloride
• Synonyms: alpha-((ethylamino)methyl)-m-hydroxybenzylalcoholhydrochloride;3-[2-(ETHYLAMINO)-1-HYDROXYETHYL]PHENOL HYDROCHLORIDE;2-ETHYLAMINO-1-(3-HYDROXYPHENYL)ETHANOL HYDROCHLORIDE;LABOTEST-BB LT00244796;dl-n-ethylnorphenylephrine hydrochloride;ETILEFRINE HCL;ETILEFRINE HYDROCHLORIDE;ETILEFRIN HYDROCHLORIDE
• CAS NO: 943-17-9
• Molecular Formula: C₁₀H₁₅NO₂*ClH
• Molecular Weight: 217.69
• EINECS: 213-398-8
• Mol File: 943-17-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 122 °C
• Boiling Point: 351.7 °C at 760 mmHg
• Flash Point: 155.5 °C
• Appearance: white
• Vapor Pressure: 1.5E-05mmHg at 25°C
• Solubility: Freely soluble in water, soluble in ethanol (96 per cent), practically insoluble in methylene chloride
• CAS DataBase Reference: Etilefrine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Etilefrine hydrochloride(943-17-9)
• EPA Substance Registry System: Etilefrine hydrochloride(943-17-9)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• RTECS: DO5618000
• Hazardous Substances Data: 943-17-9(Hazardous Substances Data)

Usage

Uses

Adrenoceptor agonist.

InChI:InChI=1/C10H15NO2.ClH/c1-2-11-7-10(13)8-4-3-5-9(12)6-8;/h3-6,10-13H,2,7H2,1H3;1H

Synthetic route

Apocretin (943-17-9) + (+)-<(R)-Tetrahydrofurfuryl-(1S)-campher-sulfonat> → N-<(R)-Tetrahydrofurfuryl>-(+/-)-etilefrin

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 100℃; for 10h;	94%

Apocretin (943-17-9) → N-Ethyl-2-chloro-2-(3-hydroxyphenyl)ethylamine hydrochloride (119610-62-7)

Conditions	Yield
With thionyl chloride In benzene at 40 - 45℃; for 1h;	46%

Apocretin (943-17-9) → 1-(3-Hydroxyphenyl)-2-ethylaminoethylthiophosphoric acid (119610-65-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / SOCl2 / benzene / 1 h / 40 - 45 °C 2: 18 percent / Na3SPO3*12H2O / H2O / 4 h View Scheme

Apocretin (943-17-9) → 1-(3-Hydroxyphenyl)-2-ethylaminoethylthiosulfuric acid (119610-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / SOCl2 / benzene / 1 h / 40 - 45 °C 2: 57 percent / Na2S2O3*5H2O / H2O / 1.) 40 deg C, 3 h, 2.) 60 deg C, 4 h View Scheme

copper(II) choride dihydrate + Apocretin (943-17-9) → Cu(α-[(etylamino)methyl]-3-hydroxy-benzenemethanol)2 (307975-81-1)

Conditions	Yield
In water at excess of ligand (1:2-1:10) and pH=10.5;

methanol (67-56-1) + copper(II) choride dihydrate + Apocretin (943-17-9) → Cu2(α-[(etylamino)methyl]-3-hydroxy-benzenemethanol)2Cl2 (307975-83-3)

Conditions	Yield
With NaOH In methanol ligand dissolved in MeOH, added methanolic solns. of CuCl2*2H2O and NaOHat molar ratio Cu-ligand-NaOH=1:2:2, allowed to stand for 3 d; filtered, washed with MeOH, dried over P2O5, elem. anal.;

methanol (67-56-1) + copper(II) choride dihydrate + Apocretin (943-17-9) → Cu(α-[(ethylamino)methyl]-3-hydroxy-benzenemethanol)2*2MeOH

Conditions	Yield
With NaOH In methanol ligand dissolved in MeOH, added methanolic solns. of CuCl2*2H2O and NaOHat molar ratio Cu-ligand-NaOH=1:10:20, allowed to stand for 4 mo; filtered, washed, dried over P2O5, elem. anal.;

Downstream Products

• 307975-83-3 Cu2(α-[(etylamino)methyl]-3-hydroxy-benzenemethanol)2Cl2 
• 307975-81-1 Cu(α-[(etylamino)methyl]-3-hydroxy-benzenemethanol)2 
• 119610-63-8 1-(3-Hydroxyphenyl)-2-ethylaminoethylthiosulfuric acid 
• 119610-65-0 1-(3-Hydroxyphenyl)-2-ethylaminoethylthiophosphoric acid 
• 119610-62-7 N-Ethyl-2-chloro-2-(3-hydroxyphenyl)ethylamine hydrochloride