1H-Indole-3-acetic acid propyl ester

Base Information

• Chemical Name: 1H-Indole-3-acetic acid propyl ester
• CAS No.: 2122-68-1
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.2637
• Hs Code.: 2933990090
• Mol file: 2122-68-1.mol

Synonyms:1H-Indole-3-acetic acid propyl ester;1H-Indole-3-acetic acid p...;propyl 2-(1H-indol-3-yl)acetate

Chemical Property of 1H-Indole-3-acetic acid propyl ester

Chemical Property:

• Melting Point: 105 °C
• Boiling Point: 365.7±17.0 °C(Predicted)
• PKA: 16.65±0.30(Predicted)
• PSA: 42.09000
• Density: 1.157±0.06 g/cm3(Predicted)
• LogP: 2.66360

Purity/Quality:

98%,99%, ^*data from raw suppliers

Propyl2-(1H-Indol-3-yl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-3-acetic acid propyl ester

There total 2 articles about 1H-Indole-3-acetic acid propyl ester 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: 99.0%

propan-1-ol (71-23-8) + indole-3-acetic acid (87-51-4) → propyl 2-(1H-indol-3-yl)acetate (2122-68-1)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 2.5h;

DOI:10.1021/jo4023149

Reference yield:

indole-3-acetic acid (87-51-4) + 1-diazopropane (764-02-3) → propyl 2-(1H-indol-3-yl)acetate (2122-68-1)

Guidance literature:

With diethyl ether;

Reference yield:

propyl 2-(1H-indol-3-yl)acetate (2122-68-1) → 1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine (4802-79-3)

Guidance literature:

Multi-step reaction with 12 steps

1: N-Bromosuccinimide / dichloromethane / 2 h / 0 °C / Inert atmosphere

2: dmap / dichloromethane / 0.5 h / 20 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylamine; copper(l) iodide / 1,2-dimethoxyethane / 3.5 h / 70 °C / Inert atmosphere

4: hydrogen; palladium 10% on activated carbon / ethyl acetate / 0.75 h / Inert atmosphere

5: diisobutylaluminium hydride / tetrahydrofuran / 0.25 h / 0 °C

6: dimethyl sulfoxide; sulfur trioxide pyridine complex; triethylamine / dichloromethane / 2 h / 0 °C

7: sodium acetate; hydroxylamine hydrochloride / isopropyl alcohol / 1.5 h / 20 °C

8: methyl orange; sodium cyanoborohydride; hydrogenchloride / methanol / 1 h / 20 °C

9: sodium cyanoborohydride / tert-butyl alcohol / 16 h / Inert atmosphere; Sealed tube; Microwave irradiation

10: zinc; trifluoroacetic acid; water / dichloromethane / 20 °C

11: thionyl chloride / dichloromethane / 3 h / 40 °C / Sealed tube

12: sodium hydroxide / dichloromethane

With hydrogenchloride; dmap; N-Bromosuccinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; palladium 10% on activated carbon; hydroxylamine hydrochloride; methyl orange; water; hydrogen; sodium acetate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; isopropylamine; triethylamine; trifluoroacetic acid; sodium hydroxide; zinc; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; isopropyl alcohol; tert-butyl alcohol; 6: |Parikh-Doering Oxidation;

DOI:10.1021/jo4023149

upstream raw materials:

propan-1-ol

indole-3-acetic acid

1-diazopropane

Downstream raw materials:

1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine

Refernces

• 1、 Fatum, Tine M.,Anthoni, Uffe,Christophersen, Carsten,Nielsen, Per Halfdan. "Stereochemistry of dimerisation of indole-3-acetic acid and its propyl ester". . p. 784 - 789. Retrieved 2007/10/03.