190274-01-2

Basic information

• Product Name: 2-Amino-7-fluoroquinazoline
• Synonyms: 2-Amino-7-fluoroquinazoline;2-Quinazolinamine,7-fluoro-(9CI);7-fluoroquinazolin-2-amine
• CAS NO: 190274-01-2
• Molecular Formula: C8H6FN3
• Molecular Weight: 163.1517432
• EINECS: 604-604-1
• Product Categories: HALIDE
• Mol File: 190274-01-2.mol

Chemical Properties

• Boiling Point: 373.659 °C at 760 mmHg
• Flash Point: 179.783 °C
• Appearance: /
• Density: 1.401 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 2-Amino-7-fluoroquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-7-fluoroquinazoline(190274-01-2)
• EPA Substance Registry System: 2-Amino-7-fluoroquinazoline(190274-01-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 190274-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
2-Amino-7-fluoroquinazoline is utilized as a key building block in the synthesis of various organic compounds and materials. Its unique structure and properties make it a valuable component in the development of new drugs, especially those targeting cancer and inflammatory conditions.
Used in Drug Synthesis:
In the pharmaceutical industry, 2-Amino-7-fluoroquinazoline is employed as a precursor for the creation of novel therapeutic agents. Its presence in the molecular structure of potential drugs can contribute to their efficacy and selectivity, making it an important tool for medicinal chemists.
Used in Medicinal Chemistry:
2-Amino-7-fluoroquinazoline is used as a versatile intermediate in medicinal chemistry for the design and synthesis of bioactive molecules. Its ability to be modified and incorporated into complex molecular frameworks positions it as a promising candidate for the advancement of pharmaceutical agents with improved pharmacological profiles.
Used in Biochemical Research:
In the field of biochemistry, 2-Amino-7-fluoroquinazoline serves as a research tool to study the interactions of various biomolecules. Its unique chemical properties allow it to be used in assays and screenings to identify potential drug targets and understand the mechanisms of action of new compounds.
Overall, 2-Amino-7-fluoroquinazoline is a significant compound in the pharmaceutical and biotechnology sectors due to its potential therapeutic applications and its role as a synthetic building block for the development of innovative drugs and materials.

InChI:InChI=1/C8H6FN3/c9-6-2-1-5-4-11-8(10)12-7(5)3-6/h1-4H,(H2,10,11,12)

Upstream product

• 1550-35-2 2,4-difluorobenzaldehyde 
• 593-85-1 diguanidine carbonate 
• 593-85-1 guanidine carbonate 
• 1256355-30-2 (5-fluoro-2-formylphenyl)boronic acid 
• 50-01-1 guanidine hydrochloride 
• 113-00-8 guanidine nitrate 

Relevant articles and documents

2-Aminoquinazolines by Chan-Evans-Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids

A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan-Evans-Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.

Discovery of novel aminoquinazolin-7-yl 6,7-dihydro-indol-4-ones as potent, selective inhibitors of heat shock protein 90

A novel class of Hsp90 inhibitors, structurally distinct from previously reported scaffolds, was developed from rational design and optimization of a compound library screen hit. These aminoquinazoline derivatives, represented by compound 15 (SNX-6833) or 1-(2-amino-4-methylquinazolin-7-yl)-3,6,6-trimethyl-6, 7-dihydro-1H-indol-4(5H)-one, selectively bind to Hsp90 and inhibit its cellular activities at concentrations as low as single digit nanomolar.

Isoquinoline, Quinazoline and Phthalazine Derivatives

Disclosed are compounds and pharmaceutically acceptable salts of Formula I wherein R0, R5, R6, R7, n, Q1-Q5, Y, and X1-X3 are as defined herein. Compounds of Formula I are useful in the treatment of diseases and/or conditions related to cell proliferation, such as cancer, inflammation, arthritis, angiogenesis, or the like. Also disclosed are pharmaceutical compositions comprising compounds of the invention and methods of treating the aforementioned conditions using such compounds.

Synthesis of 2-Aminoquinazolines from ortho-Fluorobenzaldehydes

The reaction of guanidine carbonate with various ortho-fluorobenzaldehydes in N,N-dimethylacetamide was investigated as a potential route for preparing 2-aminoquinazolines. Eleven new 2-aminoquinazolines were elaborated in this manner in low to moderate yields. In general the best results were obtained with ortho-fluorobenzaldehydes possessing an electron withdrawing substituent at the other ortho position. Complex mixtures were obtained using 2-fluorobenzaldehyde, 2,5-difluorobenzaldehyde and 2-fluoro-5-methoxybenzaldehyde which were not resolved.