30683-38-6

Usage

Uses

Used in Organic Synthesis:
4,5,6,7-Tetrafluoroindole-3-carboxaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a versatile building block for the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Production:
4,5,6,7-TETRAFLUOROINDOLE-3-CARBOXALDEHYDE is utilized as a reagent in the production of pharmaceuticals. Its unique chemical properties allow for the creation of new drug candidates with improved efficacy and selectivity. It can be incorporated into the molecular structures of drugs to enhance their pharmacological properties, such as potency, stability, and bioavailability.
Used in Agrochemical Development:
4,5,6,7-Tetrafluoroindole-3-carboxaldehyde is also employed in the development of agrochemicals. Its incorporation into the molecular structures of agrochemicals can lead to the creation of new compounds with enhanced pesticidal or herbicidal properties, improving crop protection and yield.
Used in Fine Chemicals Production:
4,5,6,7-TETRAFLUOROINDOLE-3-CARBOXALDEHYDE is used as a reagent in the production of various fine chemicals, which are high-purity chemicals used in a wide range of applications, including fragrances, flavors, dyes, and specialty chemicals. Its unique properties can contribute to the development of new fine chemicals with improved performance and functionality.
Used in Medicinal and Material Science Research:
4,5,6,7-Tetrafluoroindole-3-carboxaldehyde serves as a valuable tool in medicinal and material science research. Its unique chemical properties make it an attractive candidate for the development of new therapeutic agents, diagnostic tools, and materials with novel properties. Researchers can use 4,5,6,7-TETRAFLUOROINDOLE-3-CARBOXALDEHYDE to explore its potential applications in various areas, such as drug discovery, bioimaging, and the development of advanced materials for various industries.

InChI:InChI=1/C9H3F4NO/c10-5-4-3(2-15)1-14-9(4)8(13)7(12)6(5)11/h1-2,14H

Upstream product

• 108-24-7 acetic anhydride 
• 88752-67-4 1-benzoyl-3-methyl-4,5,6,7-tetrafluoroindole 
• 88752-66-3 1-acetyl-3-methyl-4,5,6,7-tetrafluoroindole 
• 16264-67-8 4,5,6,7-tetrafluoro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 28834-98-2 3-methyl-4,5,6,7-tetrafluoroindole 
• 95264-58-7 1-allyl-3-methyl-4,5,6,7-tetrafluoroindole 
• 122489-97-8 Allyl-[2-pentafluorophenyl-prop-(E)-ylidene]-amine 
• 122489-97-8 Allyl-[2-pentafluorophenyl-prop-(E)-ylidene]-amine 
• 80841-12-9 2-(pentafluorophenyl)propanal 

Downstream Products

• 88752-74-3 2-phenyl-4-<(1-acetyl-4,5,6,7-tetrafluoroindolyl)methylidene>-5-oxazolone 
• 88752-73-2 N-benzoyl-4,5,6,7-tetrafluorotryptophan methyl ester 
• 122490-01-1 methyl (Z)-2-benzamido-3-(4,5,6,7-tetrafluoroindolyl)-2-propenoate 
• 88752-72-1 (Z)-2-Benzoylamino-3-(4,5,6,7-tetrafluoro-1H-indol-3-yl)-acrylic acid methyl ester 
• 124614-50-2 4,5,6,7-tetrafluoro-1H-indole-3-carboxylic acid 

Relevant academic research and scientific papers

New and Effective Routes to Fluoro Analogues of Aliphatic and Aromatic Amino Acids

New and efficient syntheses of 4,4,4-trifluorovaline (1), 5,5,5-trifluoronorvaline (2), 5,5,5-trifluoroleucine (5), 6,6,6-trifluoronorleucine (6), 4,5,6,7-tetrafluorotryptophan (25), and α-(trifluoromethyl)-β-alanine are studied.Trifluorovaline (1) and trifluoronorvaline (2) are synthesized through amidocarbonylation of 2-(trifluoromethyl)propanal (2-TFMPA) and 3-(trifluoromethyl)propanal (3-TFMPA), respectively, followed by hydrolysis.Trifluoroleucine (5) and trifluoronorleucine (6) are synthesized by using modified Erlenmeyer's azlactone method from 2-TFMPA and 3-TFMPA, respectively. (S)- and (R)-trifluoronorvalines and trifluoronorleucines with high enantiomeric purities (95-100percent ee) are obtained through enzymatic optical resolution of N-acetyltrifluoronorvaline (4) and N-acetyltrifluoronorleucine (17) with the use of a porcine kidney acylase I.Optically active trifluoronorleucine is also obtained via the asymmetric hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (10a-Z) with a chiral rhodium catalyst, ClO4, followed by hydrolysis.Unexpectedly high diastereoselectivities (80-87percent ee) are observed in the hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (11b) and (Z)-N-benzoyl-4-(pentafluorophenyl)dehydronorvaline (14-Z) over palladium/carbon. 4,5,6,7-Tetrafluorotryptophan (25) and 4,5,6,7-tetrahydrotryptamine (30) are synthesized from 3-formyl-4,5,6,7-tetrafluoroindole (22a) in 51percent (four steps) and 83percent (two steps) overall yields, respectively. 4,5,6,7-Tetrafluoroindoleacetic acid (28) is obtained from 1-acetyl-3-(acetoxymethyl)-4,5,6,7-tetrafluoroindole (23a) in four steps in 65percent overall yield.The 3-formyl- and 1-acetyl-3-(acetoxymethyl)tetrafluoroindoles (22a, 23a) are prepared through selenium dioxide oxidation of 1-acyl-3-methyl-4,5,6,7-tetrafluoroindole (21), which is obtained via the cyclization of a Schiff base of 2-(pentafluorophenyl)propanal (2-PFPPA), in good yields.

Polyfluoroaralkyl amines. Further studies on the reactivity of 4,5,6,7-tetrafluoroindole

4,5,6,7-tetrafluoroindole 1 undergoes electrophilic formylation and aminoalkylation at C-3 to give compounds that can be readily converted to a variety of products, including the skatole, tryptamine, and tryptophan. 1 reacts with ethyl diazoacetate to yield 4,5,6,7-tetrafluoroethyl-3-indole acetate.The Grignard reagent of 1 offers a direct route to the versatile substituted acetonitrile 10 via C-3 alkylation with chloroacetonitrile.Key words: tetrafluoroindole, tetrafluorotryptamine, tetrafluoroindolyl magnesium bromide, tetrafluorotryptophan.

SELENIUM DIOXIDE OXIDATION OF 3-METHYL-4,5,6,7-TETRAFLUOROINDOLES: AN EFFICIENT ROUTE TO TETRAFLUORO ANALOGS OF 3-FORMYL AND 3-ACETOXYMETHYLINDOLE SYSTEMS

Selenium dioxide oxidations of 3-methyl-4,5,6,7-tetrafluoroindoles gave 3-formyl or 3-acetoxymethyltetrafluoroindoles in unexpectedly high selectivities, which turned out to serve as useful intermediates for the syntheses of tetrafluoro analogs of tryptop