443-75-4

Basic information

• Product Name: 6-FLUOROINDOLE-3-ACETIC ACID
• Synonyms: 6-FLUOROINDOLE-3-ACETIC ACID;6-F-IAA;(6-Fluoroindol-3-yl)aceticacid;6-FLUOROINDOLE-3-ACETIC ACID(6FIAA);2-(6-fluoro-1H-indol-3-yl)acetic acid;(6-Fluoro-1H-indol-3-yl)acetic acid;3-(Carboxymethyl)-6-fluoro-1H-indole
• CAS NO: 443-75-4
• Molecular Formula: C₁₀H₈FNO₂
• Molecular Weight: 193.17
• EINECS: 207-141-9
• Product Categories: Indoles and derivatives;Heterocycles series;Indole
• Mol File: 443-75-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 159-163°C
• Boiling Point: 154.5°Cat760mmHg
• Flash Point: 47.7°C
• Appearance: /
• Density: 1.186g/cm³
• Vapor Pressure: 4.08mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.38±0.30(Predicted)
• CAS DataBase Reference: 6-FLUOROINDOLE-3-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUOROINDOLE-3-ACETIC ACID(443-75-4)
• EPA Substance Registry System: 6-FLUOROINDOLE-3-ACETIC ACID(443-75-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 443-75-4(Hazardous Substances Data)

Usage

Uses

6-Fluoroindole-3-acetic Acid is a halogenated indole 3-acetic acid derivative that contains a bulky electron withdrawing fluorine making it more favorable for inhibitory activity related to cancer therapy.

InChI:InChI=1/C7H6ClF/c1-5-6(8)3-2-4-7(5)9/h2-4H,1H3

Upstream product

• 343-93-1 1-(6-fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine 
• 151-50-8 potassium cyanide 
• 399-51-9 6-fluoro-1H-indole 
• 2341-25-5 2-(6-fluoro-1H-indol-3-yl)acetonitrile 

Downstream Products

• 5159-07-9 C₁₁H₁₀FNO₂ 
• 1181283-56-6 N-(1-(4-(dimethylamino)-4-phenylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-(6-fluoro-1H-indol-3-yl)-N-methylacetamide 

Relevant articles and documents

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

Use of indole-3-acetic acid derivatives in medicine

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT

Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy

Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical surviving fractions of -3 after incubation for 2 h with 100 μM prodrug and HRP.