Efaroxan

Base Information

• Chemical Name: Efaroxan
• CAS No.: 89197-32-0
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.283
• Hs Code.: 2934999090
• UNII: G00490L21H
• DSSTox Substance ID: DTXSID8045149
• Nikkaji Number: J258.439E
• Wikipedia: Efaroxan
• Wikidata: Q5347187
• NCI Thesaurus Code: C72923
• Pharos Ligand ID: Y27Q6VUXSYM6
• ChEMBL ID: CHEMBL57895
• Mol file: 89197-32-0.mol

Synonyms:2-((2-ethyl-2,3-dihydrobenzofuran-2-yl))-2-imidazoline;efaroxan;efaroxan hydrochloride

Chemical Property of Efaroxan

Chemical Property:

• Vapor Pressure: 7.56E-06mmHg at 25°C
• Boiling Point: 387°C at 760 mmHg
• Flash Point: 187.9°C
• PSA: 33.62000
• LogP: 1.53640
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 216.126263138
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

95+% ^*data from raw suppliers

Efaroxan hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC2=CC=CC=C2O1)C3=NCCN3
• Uses: insulin secretagogue, alpha2 adrenorecetor antagonist

Technology Process of Efaroxan

There total 11 articles about Efaroxan 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: 65.0%

2-Ethyl-2,3-dihydro-benzofuran-2-carboxylic acid ethyl ester + ethylenediamine (107-15-3,85404-18-8) → efaroxan (89197-32-0,143249-88-1)

Guidance literature:

With trimethylaluminum; In toluene; for 3h; Heating;

DOI:10.1016/S0960-894X(99)00531-4

Reference yield:

2,3-dihydro-2-ethylbenzofurancarboxylic acid (111080-50-3) → efaroxan (89197-32-0,143249-88-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / ethanol / Heating

2: 65 percent / AlMe₃ / toluene / 3 h / Heating

With thionyl chloride; trimethylaluminum; In ethanol; toluene; 1: Esterification / 2: Cycloaddition;

DOI:10.1016/S0960-894X(99)00531-4

Reference yield:

2-Fluorobenzaldehyde (446-52-6) → efaroxan (89197-32-0,143249-88-1)

Guidance literature:

Multi-step reaction with 6 steps

1: t-BuOK / dioxane / 16 h / 20 °C

2: 89 percent / H₂ / 10 percent Pd/C / ethanol / 16 h

3: 1 N aq. NaOH / tetrahydrofuran / 48 h / 20 °C

4: 72 percent / NaH / toluene; dimethylformamide / 16 h / 110 °C

5: SOCl₂ / ethanol / Heating

6: 65 percent / AlMe₃ / toluene / 3 h / Heating

With sodium hydroxide; thionyl chloride; potassium tert-butylate; hydrogen; trimethylaluminum; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; N,N-dimethyl-formamide; toluene; 1: Darzens condensation / 2: Hydrogenation / 3: Hydrolysis / 4: Cyclization / 5: Esterification / 6: Cycloaddition;

DOI:10.1016/S0960-894X(99)00531-4

upstream raw materials:

2-ethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid nitrile

ethylenediamine

2,3-dihydro-2-ethylbenzofurancarboxylic acid

2-Fluorobenzaldehyde

Refernces

• 1、 Chapleo, Christopher B.,Myers, Peter L.,Butler, Richard C. M.,Davis, John A.,Doxey, John C.,et al.. "α-Adrenoreceptor Reagents. 2. Effects of Modification of the 1,4-Benzodioxan Ring System on α-Adrenoreceptor Activity". . p. 570 - 576. Retrieved 2007/10/02.