392-13-2

Basic information

• Product Name: 5-Fluoro-3-methylindole
• Synonyms: 5-FLUORO-3-METHYLINDOLE;1H-5-FLUORO-3-METHYLINDOLE;5-Fluoro-3-methyl-1H-indole;1H-5-Fluoro-3-methyindole;1H-Indole, 5-fluoro-3-methyl-
• CAS NO: 392-13-2
• Molecular Formula: C₉H₈FN
• Molecular Weight: 149.16
• EINECS: 1533716-785-6
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indole
• Mol File: 392-13-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 83.0 to 87.0 °C
• Boiling Point: 269.2 °C at 760 mmHg
• Flash Point: 116.6 °C
• Appearance: Off-white powder
• Density: 1.219 g/cm³
• Vapor Pressure: 0.0122mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 16.46±0.30(Predicted)
• CAS DataBase Reference: 5-Fluoro-3-methylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Fluoro-3-methylindole(392-13-2)
• EPA Substance Registry System: 5-Fluoro-3-methylindole(392-13-2)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 36/37/39-45
• Hazardous Substances Data: 392-13-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

5-Fluoro-3-methylindole is used to study its ionization potential and the origin of nonexponential tryptophan fluorescnece decay in proteins.

InChI:InChI=1/C9H8FN/c1-6-5-11-9-3-2-7(10)4-8(6)9/h2-5,11H,1H3

Upstream product

• 2338-71-8 5-fluoro-1H-indole-3-carbaldehyde 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 123-38-6 propionaldehyde 
• 67-56-1 methanol 
• 399-52-0 5-fluoro-1H-indole 
• 371-14-2 4-fluorophenylhydrazine 
• 202865-73-4 2-bromo-4-fluoro-1-iodobenzene 
• 107-11-9 1-amino-2-propene 
• 16381-46-7 5-fluoro-3-methyl-indole-2-carboxylic acid 

Downstream Products

• 1428236-51-4 C₂₀H₁₈FNO₃ 
• 1609470-54-3 C₁₇H₁₄F₃NO₂S 
• 1035805-54-9 5-fluoro-3-methylindolin-2-one 
• 1068968-04-6 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide 
• 1068968-07-9 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-indol-1-yl)amide 
• 1004541-73-4 (+/-)-2-(4-(Dimethylamino)-4-phenylcyclohex-1-enyl)-3-methyl-5-fluoro-1H-indole 

Relevant articles and documents

Annulative π-Extension (APEX) of Indoles to Pyrido[1,2- a]indoles Using 4-Oxo Peroxides as C4 Units

Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Br?nsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature.

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

N-Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o-Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines

Described herein is an unprecedented N-Alkylation-initiated redox-neutral [5 + 2] annulation of 3-Alkylindoles with o-Aminobenzaldehydes via a cascade N-Alkylation/dehydration/[1,5]-hydride transfer/Friedel-Crafts alkylation sequence. A series of indole-1,2-fused 1,4-benzodiazepines are facilely constructed in moderate to good yields in one step. This protocol features excellent regioselectivity, metal-free conditions, high step economy, and wide substrate scope.