9-Fluoreneacetic acid

Base Information

• Chemical Name: 9-Fluoreneacetic acid
• CAS No.: 6284-80-6
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 29163900
• European Community (EC) Number: 613-090-7
• NSC Number: 5255
• DSSTox Substance ID: DTXSID50212015
• Nikkaji Number: J414.333G
• Wikidata: Q63395574
• ChEMBL ID: CHEMBL44381
• Mol file: 6284-80-6.mol

Synonyms:9-fluoreneacetate;9-fluoreneacetic acid

Chemical Property of 9-Fluoreneacetic acid

Chemical Property:

• Appearance/Colour: light yellow crystalline powder
• Melting Point: 133-135 °C(lit.)
• Refractive Index: 1.6600 (estimate)
• Boiling Point: 436.9 °C at 760 mmHg
• PKA: 3.90±0.10(Predicted)
• Flash Point: 333.6 °C
• PSA: 37.30000
• Density: 1.242 g/cm³
• LogP: 3.27360
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

≥ 97% ^*data from raw suppliers

9-Fluoreneacetic Acid >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)CC(=O)O
• General Description: Fluorene-9-acetic acid is a chemical compound used in the synthesis of modified peptide nucleic acids (PNAs), where it serves as a component for attaching fluorophores without disrupting DNA binding affinity. Its incorporation into γ-substituted PNA backbones enables fluorescence activation upon DNA hybridization, making it valuable for developing PNA-based biosensors and molecular beacons for diagnostic applications.

Technology Process of 9-Fluoreneacetic acid

There total 2 articles about 9-Fluoreneacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

9-fluorenone (486-25-9,952573-42-1) + ethylene glycol (107-21-1) → 9-Fluorenol (1689-64-1) + (9H-fluoren-9-yl)-acetic acid (6284-80-6)

Guidance literature:

at 180 ℃;

Reference yield:

9-fluorenone (486-25-9,952573-42-1) → 9-Fluorenol (1689-64-1) + (9H-fluoren-9-yl)-acetic acid (6284-80-6)

Guidance literature:

Reference yield: 90.0%

(9H-fluoren-9-yl)-acetic acid (6284-80-6) + (4-{(2R,3R,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]pyrrolidin-1yl}butyl)amine (1450833-88-1) → C45H48N2O4 (1450834-11-3)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; at 20 ℃; for 5h;

DOI:10.1016/j.bmc.2013.06.054

upstream raw materials:

9-fluorenone

ethylene glycol

Downstream raw materials:

9H-fluorene-9-acetic acid ethyl ester

9-methylfluorene

fluoren-9-yl-acetic acid-(2-diethylamino-ethyl ester); hydrochloride

3-{4-[(2-9H-Fluoren-9-yl-acetylamino)-methyl]-phenyl}-propionic acid ethyl ester

Refernces

Synthesis of γ-substituted peptide nucleic acids: A new place to attach fluorophores without affecting DNA binding

10.1021/ol051143z

This research aims to develop a novel method for attaching fluorophores to peptide nucleic acids (PNAs) without compromising their DNA binding affinity. The study introduces a strategy involving the use of γ-lysine PNA monomers, which allow fluorophores to be covalently attached to the PNA backbone. Key chemicals used in this research include Fmoc-protected lysine-derived side chains, MiniPEG linkers, and 9-fluoreneacetic acid. The researchers synthesized PNA oligomers incorporating these modified monomers and demonstrated that these modifications did not adversely affect the thermal stability or binding affinity of the PNA to DNA. Upon annealing with complementary DNA, the modified PNA oligomers exhibited a 4-fold increase in fluorescence intensity, indicating successful quenching and activation of the fluorophore. The study concludes that this new method of PNA modification could facilitate the design of more efficient PNA-based molecular beacons and biosensors, potentially leading to improved tools for nucleic acid detection in various diagnostic applications.

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