2-(6-bromo-1H-indol-3-yl)ethanamine

Base Information

• Chemical Name: 2-(6-bromo-1H-indol-3-yl)ethanamine
• CAS No.: 96624-18-9
• Molecular Formula: C10H11BrN2
• Molecular Weight: 239.115
• Hs Code.: 2933990090
• Mol file: 96624-18-9.mol

Synonyms:6-bromotryptamine;

Chemical Property of 2-(6-bromo-1H-indol-3-yl)ethanamine

Chemical Property:

• Vapor Pressure: 1.74E-06mmHg at 25°C
• Boiling Point: 396.2°C at 760 mmHg
• PKA: 16.28±0.30(Predicted)
• Flash Point: 193.4°C
• PSA: 41.81000
• Density: 1.547g/cm³
• LogP: 3.13190
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

2-(6-BROMO-1H-INDOL-3-YL)ETHANAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(6-bromo-1H-indol-3-yl)ethanamine

There total 10 articles about 2-(6-bromo-1H-indol-3-yl)ethanamine 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:

indole-3-glyoxylamide (5548-10-7) → 5-bromotryptamine (3610-42-2) + 6-bromotryptamine (96624-18-9)

Guidance literature:

With dimethylsulfide borane complex; bromine; Multistep reaction. Title compound not separated from byproducts; 1) CH₃COOH, 15 deg C, 40 min, 2) THF, reflux, 2 h;

DOI:10.1016/S0040-4020(98)00306-8

Reference yield:

3-(2-nitrovinyl)-6-bromo-1H-indole (319493-07-7) → tryptamine (61-54-1) + 6-bromotryptamine (96624-18-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 22h; Overall yield = 77 percent; Overall yield = 2.04 g; Cooling with ice; Reflux;

DOI:10.1016/j.tet.2021.132055

Reference yield:

4-Methyl-3-nitroanilin (119-32-4) → tryptamine (61-54-1) + 6-bromotryptamine (96624-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen bromide / water / 0.33 h / Reflux

1.2: 0.25 h / 0 °C

1.3: 0 °C / Heating

2.1: pyrrolidine / N,N-dimethyl-formamide / 21 h / 105 - 110 °C

2.2: 3 h / 70 - 90 °C

3.1: trichlorophosphate / 2.5 h / 0 - 40 °C / Inert atmosphere

4.1: ammonium acetate / nitromethane / 18 h / 20 °C / Reflux

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 22 h / Cooling with ice; Reflux

With pyrrolidine; lithium aluminium tetrahydride; ammonium acetate; hydrogen bromide; trichlorophosphate; In tetrahydrofuran; nitromethane; water; N,N-dimethyl-formamide; 2.1: |Leimgruber-Batcho Indole Synthesis / 2.2: |Leimgruber-Batcho Indole Synthesis / 4.1: |Henry Nitro Aldol Condensation;

DOI:10.1016/j.tet.2021.132055

upstream raw materials:

indole-3-glyoxylamide

4-Methyl-3-nitroanilin

4-bromo-2-nitrotoluene

1-indoline

Downstream raw materials:

7-bromo-1,2,3,4-tetrahydro-β-carboline

7-bromo-9H-pyrido[3,4-b]indole

14-<(benzyloxy)methyl>didemnoline A

C₂₅H₂₀BrN₃O₃S