3-(TRIFLUOROACETYL)INDOLE

Base Information

• Chemical Name: 3-(TRIFLUOROACETYL)INDOLE
• CAS No.: 14618-45-2
• Molecular Formula: C10H6F3NO
• Molecular Weight: 213.159
• Hs Code.: 2933990090
• Mol file: 14618-45-2.mol

Synonyms:Ketone,indol-3-yl trifluoromethyl (8CI);3-(2,2,2-Trifluoroacetyl)indole;3-Indolyltrifluoromethyl ketone;

Chemical Property of 3-(TRIFLUOROACETYL)INDOLE

Chemical Property:

• Appearance/Colour: power
• Vapor Pressure: 0.000675mmHg at 25°C
• Melting Point: 211-214 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 308.6 °C at 760 mmHg
• PKA: 14.31±0.30(Predicted)
• Flash Point: 140.4 °C
• PSA: 32.86000
• Density: 1.423 g/cm³
• LogP: 2.91290
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

97% ^*data from raw suppliers

3-(Trifluoroacetyl)indole ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• General Description: 3-(Trifluoroacetyl)indole is a 3-substituted indole derivative featuring an electron-withdrawing trifluoroacetyl group, which enhances its reactivity in single electron transfer (SET) reactions with sodium naphthalenide. The presence of the trifluoroacetyl group lowers the LUMO energy of the indole ring, enabling efficient electron transfer and selective product formation. 3-(TRIFLUOROACETYL)INDOLE reacts readily with sodium naphthalenide to yield a single product, demonstrating its utility in the synthesis of indole derivatives under SET conditions.

Technology Process of 3-(TRIFLUOROACETYL)INDOLE

There total 16 articles about 3-(TRIFLUOROACETYL)INDOLE 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%

indole (120-72-9) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone (14618-45-2)

Guidance literature:

In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/acs.orglett.1c02502

Reference yield: 76.0%

(R)-2-(2,2,2-trifluoro-1-(1H-indol-3-yl)-1-((trimethylsilyl)oxy)ethyl)benzo[d]thiazole → 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone (14618-45-2)

Guidance literature:

(R)-2-(2,2,2-trifluoro-1-(1H-indol-3-yl)-1-((trimethylsilyl)oxy)ethyl)benzo[d]thiazole; In dichloromethane; at 20 ℃; for 0.166667h; Molecular sieve;

With trimethoxonium tetrafluoroborate; In dichloromethane; Further stages;

DOI:10.1021/acs.joc.0c00116

Reference yield: 73.0%

2-(1H-indol-3-yl)-4-methyl-2-(trifluoromethyl)-2,3-dihydro-6H-1,3-oxazin-6-one → 2,2,2-trifluoro-1-(1H-indol-3-yl)ethanone (14618-45-2)

Guidance literature:

With potassium hydroxide; for 15h;

upstream raw materials:

indole

trifluoroacetonitrile

trifluoroacetic acid

trifluoroacetic anhydride

Downstream raw materials:

2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethan-1-one

1H-indole-3-carboxylic acid

1-(indole-3-carbonyl)-pyrrolidine

N-benzenesulfonyl-3-trifluoroacetylindole

Refernces

Effect of sodium naphthalenide, a key set reagent, on 3-substituted indoles

10.3987/COM-04-10142

The research investigates the effects of sodium naphthalenide, a single electron transfer (SET) reagent, on 3-substituted indoles to explore the synthesis of indole derivatives through SET reactions. The study found that indoles with electron-donating substituents do not react with sodium naphthalenide, while those with electron-withdrawing substituents readily undergo reactions, yielding various products depending on the specific substituent. For instance, 3-trifluoroacetylindole, 3-acetylindole, and 3-benzoylindole each produced a single product, whereas 3-formylindole generated four products. The reactions involving electron-withdrawing groups were highly selective and efficient, with high yields of the desired products. The study concludes that SET reactions with sodium naphthalenide are an effective method for constructing indole derivatives when electron-withdrawing substituents are present on the indole ring, as these groups lower the LUMO energy of the indole ring, facilitating electron transfer from the reagent to the substrate.