7569-60-0

Basic information

• Product Name: 3-CHLORO-4-METHOXYPHENETHYLAMINE HYDROC&
• Synonyms: 3-Chloro-4-methoxyphenethylamine hydrochloride 90%;2-(3-Chloro-4-methoxyphenyl)ethanamine hydrochloride;3-Chloro-4-MethoxyphenethylaMine hydrochlo
• CAS NO: 7569-60-0
• Molecular Formula: C₉H₁₂ClNO*ClH
• Molecular Weight: 222.114
• Mol File: 7569-60-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 192-195 °C
• Boiling Point: 313.1°C at 760 mmHg
• Flash Point: 143.2°C
• Appearance: /
• Vapor Pressure: 0.000374mmHg at 25°C
• CAS DataBase Reference: 3-CHLORO-4-METHOXYPHENETHYLAMINE HYDROC&(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-METHOXYPHENETHYLAMINE HYDROC&(7569-60-0)
• EPA Substance Registry System: 3-CHLORO-4-METHOXYPHENETHYLAMINE HYDROC&(7569-60-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7569-60-0(Hazardous Substances Data)

Usage

General Description

3-Chloro-4-methoxyphenethylamine hydrochloride is a chemical compound that belongs to the family of phenethylamine derivatives. It is a substituted phenethylamine with a chlorine group at the 3-position and a methoxy group at the 4-position of the phenethylamine core. 3-CHLORO-4-METHOXYPHENETHYLAMINE HYDROC& is commonly used as a reagent in chemical research and pharmaceutical development. It has potential applications in studying the structure-activity relationship of phenethylamine derivatives and in the synthesis of new drugs with desired pharmacological properties. Additionally, it may also have applications in the development of psychoactive substances, although its specific psychoactive effects and potential uses in this regard have not been extensively studied.

InChI:InChI=1/C9H12ClNO.ClH/c1-12-9-3-2-7(4-5-11)6-8(9)10;/h2-3,6H,4-5,11H2,1H3;1H

Upstream product

• 55-81-2 4-Methoxyphenethylamine 

Downstream Products

• 1037078-89-9 3-chloro-4-hydroxyphenethylammonium trifluoroacetate 

Relevant articles and documents

Dopamine/serotonin receptor ligands. 121: SAR studies on hexahydro-dibenz[d,g]azecines lead to 4-chloro-7-methyl-5,6,7,8,9,14- hexahydrodibenz[d,g]azecin-3-ol, the first picomolar D5-selective dopamine-receptor antagonist

Hydroxylated, methoxylated, and/or chlorinated 7-methyl-5,6,7,8,9,14- hexahydrodibenz[d,g]azecines were generally synthesized out of substituted 2-phenylethylamines and isochromanones by Bischler-Napieralski cyclization of the resulting benzamides to dibenzoquinolizines and the quaternization and cleavage of the central C-N bond under Birch conditions. Chlorination of 2-phenylethylamines was useful for the site direction of cyclization, but chlorine atoms were removed under Birch conditions so that chlorination had to be repeated to get the respective chlorinated dibenz[d,g]azecines. The target compounds were tested for their affinity at the different human-cloned dopamine-receptor subtypes (D1 family, D2 family). Generally, hydroxylation and chlorination of the dibenz-azecines increased affinities significantly. 1-Chloro-2-hydroxyhexahydro-dibenz[d,g]azecine was a subnanomolar antagonist at both subtype families. 4-Chloro-3-hydroxy-7-methyl-5, 6,7,8,9,14-hexahydro-dibenz[d,g]azecine was identified as the most potent and selective dopamine D5 receptor ligand described to date with K i(D1) = 0.83, Ki(D2L) = 4.0, K i(D3) = 24.6, Ki(D4) = 5.2 nM, and Ki(D5) = 57 pM (radioligand binding experiments), respectively.

A mild and efficient method for aromatic chlorination of electron-rich arylalkyl amines

Sulfuryl chloride was used to chlorinate electron-rich arylalkyl amines in a mild and efficient one-pot transformation with simple product isolation via precipitation. Protection of the amine was not needed.