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Methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate is a chemical compound characterized by its molecular formula C11H8BrFO2. It is a fluorescent and aromatic compound that features a 5-membered indole ring with a bromine and a fluorine atom attached, along with an ester group at the 3-position. This versatile compound is widely utilized in organic synthesis and medicinal chemistry due to its unique structure and reactivity.

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  • 1638759-63-3 Structure
  • Basic information

    1. Product Name: methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate
    2. Synonyms:
    3. CAS NO:1638759-63-3
    4. Molecular Formula:
    5. Molecular Weight: 272.073
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1638759-63-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate(CAS DataBase Reference)
    10. NIST Chemistry Reference: methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate(1638759-63-3)
    11. EPA Substance Registry System: methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate(1638759-63-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1638759-63-3(Hazardous Substances Data)

1638759-63-3 Usage

Uses

Used in Pharmaceutical Research:
Methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate serves as a valuable building block in the development of new drugs. Its functional groups and reactivity contribute to the synthesis of various organic molecules and pharmaceutical compounds, making it instrumental in creating novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate is employed as a key intermediate for the preparation of complex organic molecules. Its unique structure allows for a range of chemical reactions, facilitating the creation of diverse chemical entities.
Used in Medicinal Chemistry:
Methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate is utilized in medicinal chemistry for the study of biological processes. Its fluorescent properties make it suitable for applications such as fluorescence imaging and the investigation of molecular interactions within biological systems.
Used in Fluorescence Imaging:
In the field of fluorescence imaging, methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate is used as a fluorescent probe for visualizing cellular structures and processes. Its fluorescence allows researchers to track and study the behavior of molecules within biological systems.
Used in Drug Development:
Methyl 5-bromo-6-fluoro-1H-indole-3-carboxylate is employed in the drug development process as a precursor for the synthesis of potential therapeutic agents. Its reactivity and functional groups enable the creation of new compounds with specific biological activities, contributing to the advancement of pharmaceutical research.

Check Digit Verification of cas no

The CAS Registry Mumber 1638759-63-3 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,6,3,8,7,5 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1638759-63:
(9*1)+(8*6)+(7*3)+(6*8)+(5*7)+(4*5)+(3*9)+(2*6)+(1*3)=223
223 % 10 = 3
So 1638759-63-3 is a valid CAS Registry Number.

1638759-63-3Relevant articles and documents

Optimization of Metabolic and Renal Clearance in a Series of Indole Acid Direct Activators of 5′-Adenosine Monophosphate-Activated Protein Kinase (AMPK)

Edmonds, David J.,Kung, Daniel W.,Kalgutkar, Amit S.,Filipski, Kevin J.,Ebner, David C.,Cabral, Shawn,Smith, Aaron C.,Aspnes, Gary E.,Bhattacharya, Samit K.,Borzilleri, Kris A.,Brown, Janice A.,Calabrese, Matthew F.,Caspers, Nicole L.,Cokorinos, Emily C.,Conn, Edward L.,Dowling, Matthew S.,Eng, Heather,Feng, Bo,Fernando, Dilinie P.,Genung, Nathan E.,Herr, Michael,Kurumbail, Ravi G.,Lavergne, Sophie Y.,Lee, Esther C.-Y.,Li, Qifang,Mathialagan, Sumathy,Miller, Russell A.,Panteleev, Jane,Polivkova, Jana,Rajamohan, Francis,Reyes, Allan R.,Salatto, Christopher T.,Shavnya, Andre,Thuma, Benjamin A.,Tu, Meihua,Ward, Jessica,Withka, Jane M.,Xiao, Jun,Cameron, Kimberly O.

, p. 2372 - 2383 (2018/03/26)

Optimization of the pharmacokinetic (PK) properties of a series of activators of adenosine monophosphate-activated protein kinase (AMPK) is described. Derivatives of the previously described 5-aryl-indole-3-carboxylic acid clinical candidate (1) were examined with the goal of reducing glucuronidation rate and minimizing renal excretion. Compounds 10 (PF-06679142) and 14 (PF-06685249) exhibited robust activation of AMPK in rat kidneys as well as desirable oral absorption, low plasma clearance, and negligible renal clearance in preclinical species. A correlation of in vivo renal clearance in rats with in vitro uptake by human and rat renal organic anion transporters (human OAT/rat Oat) was identified. Variation of polar functional groups was critical to mitigate active renal clearance mediated by the Oat3 transporter. Modification of either the 6-chloroindole core to a 4,6-difluoroindole or the 5-phenyl substituent to a substituted 5-(3-pyridyl) group provided improved metabolic stability while minimizing propensity for active transport by OAT3.

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