3,4-Dimethoxyphenethylamine

Base Information

• Chemical Name: 3,4-Dimethoxyphenethylamine
• CAS No.: 120-20-7
• Molecular Formula: C10H15NO2
• Molecular Weight: 181.235
• Hs Code.: 29222900
• European Community (EC) Number: 204-376-9
• NSC Number: 26152,16948,6328
• UNII: IQF9T435OP
• DSSTox Substance ID: DTXSID8059506
• Nikkaji Number: J28.381I
• Wikipedia: 3,4-Dimethoxyphenethylamine
• Wikidata: Q4634069
• Metabolomics Workbench ID: 49549
• ChEMBL ID: CHEMBL26019
• Mol file: 120-20-7.mol

Synonyms:Dimethoxyphenylethylamine

Chemical Property of 3,4-Dimethoxyphenethylamine

Chemical Property:

• Appearance/Colour: colorless transparent liquid
• Vapor Pressure: 0.000251mmHg at 25°C
• Melting Point: 12-15 ºC
• Refractive Index: n20/D 1.546(lit.)
• Boiling Point: 324.1 ºC at 760 mmHg
• PKA: 9.74±0.10(Predicted)
• Flash Point: 132.8 ºC
• PSA: 44.48000
• Density: 1.041 g/cm³
• LogP: 1.90530
• Storage Temp.: Refrigerator
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 181.110278721
• Heavy Atom Count: 13
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

Homoveratrylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: COC1=C(C=C(C=C1)CCN)OC
• Uses: 3,4-Dimethoxyphenethylamine is a methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies. A methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies. Precursor for the synthesis of isoquinolines.

Technology Process of 3,4-Dimethoxyphenethylamine

There total 67 articles about 3,4-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: 94.0%

(1S,4R)-2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene; hydrochloride (110098-01-6) → (1R,2S,6R,7S)-4-methyl-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione (3526-89-4,6623-18-3,56420-87-2) + 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1745-07-9) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7)

Guidance literature:

With N-methylmaleimide; In water; at 50 ℃; for 4h;

DOI:10.1021/ja00253a053

Reference yield: 82.0%

1,2-dimethoxy-4-(2-nitroethyl)benzene (70360-83-7) → 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 20 ℃; for 4h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1002/anie.201604026

Reference yield: 82.0%

2-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-aza-bicyclo[2.2.1]hept-5-ene (126424-25-7,150737-45-4) → 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7)

Guidance literature:

copper(II) sulfate; In ethanol; at 70 ℃; for 2h;

DOI:10.1021/jo00295a002

upstream raw materials:

3,4-dimethoxyphenylacetonitrile

5-bromo-3,4-dimethoxy-1-(2-nitrovinyl)benzene

(dimethoxy-3,4 phenyl)-2 methoxy-2 nitro-1 ethane

1,2-dimethoxy-4-(2-nitro-vinyl)-benzene

Downstream raw materials:

N-[2-(3,4-dimethoxyphenyl)ethyl]-2-pyrrolidone

N-<2-(3,4-dimethoxyphenyl)ethyl>-4-hydroxybutanamide

N-β-(3,4-dimethoxyphenyl)ethylvalerolactam

N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(2-thienyl)ethanamide

Refernces

• 1、 Kindler. "-". . p. 70,76. Retrieved 1931.
• 2、 Yonemitsu et al.. "-". . p. 5686,5687-5690. Retrieved 1970.
• 3、 Fan, Tian-Yun,Yang, Yu-Xin,Zeng, Qing-Xuan,Wang, Xue-Lei,Wei, Wei,Guo, Xi-Xi,Zhao, Li-Ping,Song, Dan-Qing,Wang, Yan-Xiang,Wang, Li,Hong, Bin. "Structure–activity relationship and biological evaluation of berberine derivatives as PCSK9 down-regulating agents". . . Retrieved 2021/06/01.
• 4、 -. "Preparation method of dopamine hydrochloride". . . Retrieved 2020/11/26.