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:

98%,99%, ^*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:

• Uses: Reactant for enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylation. Reactant for preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives. with indolecarboxylic acid 2 Reactant for preparation of mast cell tryptase inhibitors, starting from indoles; using amidation as the key step 3 Reactant for formation of Michael adducts via Baylis-Hillman reaction 4 Reactant for preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides. Reactant for enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylationReactant for preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives. with indolecarboxylic acidReactant for preparation of mast cell tryptase inhibitors, starting from indoles; using amidation as the key stepReactant for formation of Michael adducts via Baylis-Hillman reactionReactant for preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides

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:

1-(indole-3-carbonyl)-pyrrolidine

N-benzenesulfonyl-3-trifluoroacetylindole

5-benzoyl-3-trifluoroacetylindole

5-(4'-methylbenzoyl)-3-trifluoroacetylindole

Refernces

• 1、 Wang, Wei,Xiong, Wenhui,Wang, Jinping,Wang, Qiu-An,Yang, Wen. "Br?nsted Acid-Catalyzed Asymmetric Friedel-Crafts Alkylation of Indoles with Benzothiazole-Bearing Trifluoromethyl Ketone Hydrates". . p. 4398 - 4407. Retrieved 2020.
• 2、 Badenock, Jeanese C.,Fraser, Heidi L.,Gribble, Gordon W.. "A new approach to the pyrrolo[3,4-b]indole ring system". . p. 140 - 149. Retrieved 2018.
• 3、 Huang, Mao-Gui,Shi, Shuai,Li, Ming,Liu, Yue-Jin,Liu, Yue-Jin. "Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue". supporting information. p. 7094 - 7099. Retrieved 2021/09/14.