6-(2-Aminopropyl)-2,3-dihydrobenzofuran

Base Information

• Chemical Name: 6-(2-Aminopropyl)-2,3-dihydrobenzofuran
• CAS No.: 152623-93-3
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.246
• Hs Code.: 2932999099
• UNII: O72F3CP4O8
• DSSTox Substance ID: DTXSID60934559
• Nikkaji Number: J3.334.443K
• Wikipedia: 6-APDB
• Wikidata: Q4641530
• ChEMBL ID: CHEMBL124055
• Mol file: 152623-93-3.mol

Synonyms:6-(2-aminopropyl)-2,3-dihydrobenzofuran;6-NProp-DBF

Chemical Property of 6-(2-Aminopropyl)-2,3-dihydrobenzofuran

Chemical Property:

• Vapor Pressure: 0.00179mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 292.868 °C at 760 mmHg
• Flash Point: 134.233 °C
• PSA: 35.25000
• Density: 1.088 g/cm³
• LogP: 2.21150
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 177.115364102
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC2=C(CCO2)C=C1)N

Technology Process of 6-(2-Aminopropyl)-2,3-dihydrobenzofuran

There total 7 articles about 6-(2-Aminopropyl)-2,3-dihydrobenzofuran 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:

6-(2-aminopropyl)-2,3-dihydrobenzofuran (152623-93-3) → 1‐(2,3‐dihydro‐1‐benzofuran‐6‐yl)propan‐2‐amine (152623-93-3) + 1‐(2,3‐dihydro‐1‐benzofuran‐6‐yl)propan‐2‐amine (152623-93-3)

Guidance literature:

With isopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; isopropyl alcohol; at 35 ℃; under 103432 Torr; Reagent/catalyst; Solvent; Resolution of racemate; Supercritical conditions;

DOI:10.1002/chir.22701

Reference yield:

6-(2-aminopropyl)-2,3-dihydrobenzofuran (152623-93-3) → 1‐(2,3‐dihydro‐1‐benzofuran‐6‐yl)propan‐2‐amine (152623-93-3) + 1‐(2,3‐dihydro‐1‐benzofuran‐6‐yl)propan‐2‐amine (152623-93-3)

Guidance literature:

With isopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; isopropyl alcohol; at 35 ℃; under 103432 Torr; Reagent/catalyst; Solvent; Resolution of racemate; Supercritical conditions;

DOI:10.1002/chir.22701

Reference yield:

3-methoxyamphetamine (17862-85-0) → 6-(2-aminopropyl)-2,3-dihydrobenzofuran (152623-93-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Et₃N / 1.) CH₂Cl₂, 10 min, 2.) CH₂Cl₂, RT, 1.5 h

2: 3.5 g / AlCl₃ / 1,2-dichloro-ethane / 4 h / 45 °C

3: 1.) BBr₃, 2.) NaOAc / 1.) CH₂Cl₂, -78 deg C to RT, 12 h, 2.) CH₃OH, reflux, 1.5 h

4: H₂ / 20percent PdOH/C / ethanol / 12 h / 2689.2 Torr

5: 2N KOH / propan-2-ol / 5 h / Heating

With potassium hydroxide; aluminium trichloride; hydrogen; sodium acetate; boron tribromide; triethylamine; PdOH/C; In ethanol; 1,2-dichloro-ethane; isopropyl alcohol;

DOI:10.1021/jm00075a027

upstream raw materials:

6-<2-propyl>-2,3-dihydrobenzofuran

3-methoxyamphetamine

N-(trifluoroacetyl)-1-(3-methoxyphenyl)-2-aminopropane

6-<2-propyl>-2,3-dihydrobenzofuran-3-one

Refernces

• 1、 H?gele, Johannes S.,Schmid, Martin G.. "Enantiomeric separation of Novel Psychoactive Substances by capillary electrophoresis using (+)-18-crown-6-tetracarboxylic acid as chiral selector". . p. 1019 - 1026. Retrieved 2018/07/29.
• 2、 Monte, Aaron P.,Marona-Lewicka, Danuta,Cozzi, Nicholas V.,Nichols, David E.. "Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4-(Methylenedioxy)amphetamine". . p. 3700 - 3706. Retrieved 2007/10/02.