4-Bromo-2,5-dimethoxyphenethylamine

Base Information

• Chemical Name: 4-Bromo-2,5-dimethoxyphenethylamine
• CAS No.: 66142-81-2
• Molecular Formula: C10H14BrNO2
• Molecular Weight: 260.131
• European Community (EC) Number: 636-275-4
• UNII: V77772N32H
• DSSTox Substance ID: DTXSID10216332
• Nikkaji Number: J456.895H
• Wikipedia: 2C-B
• Wikidata: Q229942
• Pharos Ligand ID: YY6LFDU9PT33
• Metabolomics Workbench ID: 66917
• ChEMBL ID: CHEMBL292821
• Mol file: 66142-81-2.mol

Synonyms:2-(4-bromo-2,5-dimethoxyphenyl)ethylamine;2C-B;4-bromo-2,5-dimethoxyphenethylamine

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Chemical Property of 4-Bromo-2,5-dimethoxyphenethylamine

Chemical Property:

• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.548
• Boiling Point: 332.9 °C at 760 mmHg
• PKA: 9.37±0.10(Predicted)
• Flash Point: 155.1 °C
• PSA: 44.48000
• Density: 1.368 g/cm³
• LogP: 2.66780
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 259.02079
• Heavy Atom Count: 14
• Complexity: 168

Purity/Quality:

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1CCN)OC)Br
• Recent ClinicalTrials: Acute Effects of 2C-B Compared With MDMA and Psilocybin in Healthy Subjects

Technology Process of 4-Bromo-2,5-dimethoxyphenethylamine

There total 6 articles about 4-Bromo-2,5-dimethoxyphenethylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

2,5-dimethoxyphenethylamine (3600-86-0) → 2-(4-bromo-2,5-dimethoxyphenyl)-1-aminoethane (66142-81-2)

Guidance literature:

With pyridine; bromine; In tetrahydrofuran; at 20 ℃; for 24.5h; Reagent/catalyst; Solvent; regioselective reaction;

DOI:10.1016/j.tetlet.2020.152804

Reference yield:

4-bromo-2,5-dimethoxybenzaldehyde (31558-41-5) → 2-(4-bromo-2,5-dimethoxyphenyl)-1-aminoethane (66142-81-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium acetate / 1.) reflux, 6 h, 2.) RT, 16 h

2: LiAlH₄, H₂SO₄ / tetrahydrofuran / Ambient temperature

With ammonium acetate; lithium aluminium tetrahydride; sulfuric acid; In tetrahydrofuran;

DOI:10.1021/jm00082a014

Reference yield:

4-bromo-2,5-dimethoxy-β-nitrostyrene (98537-45-2,82040-76-4) → 2-(4-bromo-2,5-dimethoxyphenyl)-1-aminoethane (66142-81-2)

Guidance literature:

With lithium aluminium tetrahydride; sulfuric acid; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm00082a014

upstream raw materials:

4-bromo-2,5-dimethoxy-β-nitrostyrene

2,5-dimethoxyphenethylamine

4-bromo-2,5-dimethoxybenzaldehyde

1-bromo-2,5-dimethoxybenzene

Downstream raw materials:

[¹¹C]Cimbi-36

1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane

1-(2,5-dihydroxy-4-cyanophenyl)-2-aminoethane

1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane

Refernces

• 1、 Chatha, Muhammad,Halberstadt, Adam L.,Jademyr, Simon,Jensen, Anders A.,Klein, Adam K.,Kristensen, Jesper L.,Marcher-R?rsted, Emil. "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". . p. 1238 - 1244. Retrieved 2020/05/27.
• 2、 Xu, Ya-Zhu,Chen, Chinpiao. "Synthesis of deuterium labeled phenethylamine derivatives". . p. 1187 - 1200. Retrieved 2008/04/18.