186446-26-4

Basic information

• Product Name: 5-CHLORO-4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID
• Synonyms: 5-CHLORO-4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID;4-fluoro-5-chloroindole-2-carboxylic acid
• CAS NO: 186446-26-4
• Molecular Formula: C₉H₅ClFNO₂
• Molecular Weight: 213.5929
• Mol File: 186446-26-4.mol

Chemical Properties

• Melting Point: 270-280 °C
• Boiling Point: 455.4 °C at 760 mmHg
• Flash Point: 229.2 °C
• Appearance: /
• Density: 1.635 g/cm³
• Storage Temp.: 2-8°C
• PKA: 4.13±0.30(Predicted)
• CAS DataBase Reference: 5-CHLORO-4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID(186446-26-4)
• EPA Substance Registry System: 5-CHLORO-4-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID(186446-26-4)

Safety Data

• Hazardous Substances Data: 186446-26-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-4-fluoro-1H-indole-2-carboxylic acid is used as a key intermediate in the synthesis of pharmaceuticals for its potential pharmacological properties. It contributes to the development of drugs with anti-inflammatory and anticancer activities, offering therapeutic benefits in treating various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical industry, 5-chloro-4-fluoro-1H-indole-2-carboxylic acid is utilized as a building block for the synthesis of agrochemicals. Its unique structure and properties enable the creation of compounds with bioactivity, which can be applied in crop protection and other agricultural applications.
Used in Organic Synthesis:
5-Chloro-4-fluoro-1H-indole-2-carboxylic acid is used as a versatile building block in organic synthesis. Its presence in the synthesis of various heterocyclic compounds allows for the development of new chemical entities with potential applications in different fields, including materials science, pharmaceuticals, and agrochemicals.
Used in Research and Development:
In the research and development sector, 5-chloro-4-fluoro-1H-indole-2-carboxylic acid is employed as a valuable compound for studying its potential pharmacological properties. Its anti-inflammatory and anticancer activities are of particular interest, as they can lead to the discovery of new therapeutic agents and contribute to advancements in medicine.
Overall, 5-chloro-4-fluoro-1H-indole-2-carboxylic acid is a multifaceted chemical compound with diverse applications across various industries, making it an essential component in the development of innovative products and therapies.

Upstream product

• 127-17-3 2-oxo-propionic acid 
• 869299-68-3 1,1-dimethylethyl (4-chloro-3-fluorophenyl)carbamate 
• 1018450-37-7 4-chloro-3-fluoro-2-iodoaniline 
• 367-22-6 4-chloro-3-fluoroaniline 
• 480450-89-3 methyl 5-chloro-4-fluoro-1H-indole-2-carboxylate 

Downstream Products

• 1394078-66-0 (5-chloro-4-fluoro-1H-indol-2-yl)-(4-methyl-1,4-diazepan-1-yl)methanone 

Relevant articles and documents

PHARMACEUTICAL COMPOUND

Provided is a compound having formula (I): wherein R2 is selected from -C1, -Br and -CN; R1 and R4 are independently selected from H and -F; R631, R632, R641 and R642

Robust synthesis of methyl 5-chloro-4-fluoro-1 h -indole-2-carboxylate: A key intermediate in the preparation of an HIV NNRTI candidate

A synthetic preparation of methyl 5-chloro-4-fluoro-1H-indole-2- carboxylate, a key intermediate towards phosphoindole inhibitors of HIV non-nucleoside reverse transcriptase, is described. The five-step synthesis involved Boc protection of the commercially available 4-chloro-3-fluoroaniline and regioselective iodination at C-2. After facile Boc deprotection, cyclization of the resultant o-iodoaniline gave the corresponding 5-chloro-4-fluoro-indole- 2-carboxylic acid which was subsequently esterified to provide the target indole ester in 56% overall yield. Identification of 6-chloro-7-iodo-2(3H)- benzoxazolone as a significant side product in the iodination step led to the development of conditions which eliminated its formation in subsequent batches. Advantages of this alternative approach relative to existing methodologies include (1) potentially hazardous diazonium and azido species were not required, (2) regioisomeric products were not generated, and (3) chromatographic isolations were avoided, as all intermediates were easily crystallized. As a result, the key indole ester was produced rapidly at 100-fold increased scale compared to previous reports with a 10-fold improvement in overall yield.

Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: Exploration of 5-6 fused rings as alternative S1 moieties

A series of cis-1,2-diaminocyclohexane derivatives were synthesized with the aim of optimizing previously disclosed factor Xa (fXa) inhibitors. The exploration of 5-6 fused rings as alternative S1 moieties resulted in two compounds which demonstrated improved solubility and reduced food effect compared to the clinical candidate, compound A. Herein, we describe the synthesis and structure-activity relationship (SAR), together with the physicochemical properties and pharmacokinetic (PK) profiles of some prospective compounds.

ENANTIOMERICALLY PURE PHOSPHOINDOLES AS HIV INHIBITORS

3-phosphoindole compounds substantially in the form of a single enantiomer useful for the treatment of Flaviviridae virus infections, and particularly for HIV infections are provided. Also provided are pharmaceutical compositions comprising the 3-phosphoi

DIAMINE DERIVATIVES

A compound represented by formula (1):Q1-Q2-To-N(R1) -Q3-N(R2)-T1-Q4 [wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 represents the following group: (wherein Q5 is an alkylene group having 1 to 8 carbon atoms, or the like); and T0 and T1 are carbonyl groups or the like], a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

DIAMINE DERIVATIVES

A compound represented by the general formula (1):Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.