5-Carboxyfluorescein

Base Information

• Chemical Name: 5-Carboxyfluorescein
• CAS No.: 76823-03-5
• Molecular Formula: C21H12O7
• Molecular Weight: 376.322
• Hs Code.: 32129000
• European Community (EC) Number: 691-482-7
• UNII: AB2MM66GSF
• DSSTox Substance ID: DTXSID30227642
• Nikkaji Number: J480.059A
• Wikidata: Q27122687
• Mol file: 76823-03-5.mol

Synonyms:4(5)-carboxyfluorescein;4-carboxyfluorescein;5-carboxyfluorescein

Chemical Property of 5-Carboxyfluorescein

Chemical Property:

• Appearance/Colour: Orange solid
• Vapor Pressure: 4.5E-22mmHg at 25°C
• Melting Point: 368-372°C
• Refractive Index: 1.816
• Boiling Point: 725.2 °C at 760 mmHg
• PKA: 3.3, 4.6, 6.4, 7.0(at 25℃)
• Flash Point: 266.9 °C
• PSA: 113.29000
• Density: 1.73 g/cm³
• LogP: 3.36400
• Storage Temp.: Store at 2-8
• Solubility.: DMF: soluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 376.05830272
• Heavy Atom Count: 28
• Complexity: 637

Purity/Quality:

99% ^*data from raw suppliers

5-Carboxyfluorescein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C(=O)O)C(=O)OC23C4=C(C=C(C=C4)O)OC5=C3C=CC(=C5)O
• Description: 5-Carboxyfluorescein is a single isomer derivative of 5(6)-carboxyfluorescein that can be used to fluorescently label biomolecules through the interaction of carboxylic acid with primary amines. It demonstrates excitation/emission maxima of 492 and 518 nm, respectively.
• Uses: 5-Carboxyfluorescein(5-FAM) contains a carboxylic acid that can be used to react with primary amines via carbodiimide activation of the carboxylic acid. It is a useful reagent for the preparation of hydrolytically stable fluorescent conjugates and is a useful starting material for the synthesis of other fluorescein-derives reagent. It has been principally used to develop a variety of green fluorescent reagents and small fluorescent molecules due to its relatively high absorbance characteristics, excellent fluorescence quantum yield, and good water solubility. The probe has also found application in studies of liposome-cell, cell-cell, and liposome-liposome interactions and in related studies on lipid bilayer structures.

Technology Process of 5-Carboxyfluorescein

There total 6 articles about 5-Carboxyfluorescein 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:

recorcinol (108-46-3) + trimellitic Anhydride (552-30-7,145253-53-8) → 6-carboxyfluorescein (3301-79-9) + 5-carboxyfluoroscein (76823-03-5)

Guidance literature:

With sulfuric acid; at 130 ℃; for 0.04h; Title compound not separated from byproducts; Irradiation;

Reference yield:

benzyl chloride (100-44-7) + recorcinol (108-46-3) + trimellitic Anhydride (552-30-7,145253-53-8) → 6-carboxyfluorescein (3301-79-9) + 5-carboxyfluoroscein (76823-03-5)

Guidance literature:

recorcinol; trimellitic Anhydride; With zinc(II) chloride; at 200 ℃; for 2h;

benzyl chloride; With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 19h;

With 5%-palladium/activated carbon; hydrogen; In methanol; ethyl acetate; at 20 ℃;

DOI:10.1016/j.saa.2016.06.021

Reference yield:

recorcinol (108-46-3) + trimellitic Anhydride (552-30-7,145253-53-8) → 5-carboxyfluoroscein (76823-03-5)

Guidance literature:

With methanesulfonic acid; at 80 - 85 ℃; for 12h;

DOI:10.1039/b309196a

upstream raw materials:

recorcinol

trimellitic Anhydride

5-Carboxyfluorescein diacetate

benzyl chloride

Downstream raw materials:

fluorescein

Refernces

• 1、 -. "ULTRA BRIGHT DIMERIC OR POLYMERIC DYES WITH SPACING LINKER GROUPS". Paragraph 0412. . Retrieved 2017/11/01.
• 2、 Sato, Shingo,Endo, Susumu,Kurokawa, Yusuke,Yamaguchi, Masaki,Nagai, Akio,Ito, Tomohiro,Ogata, Tateaki. "Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds". supporting information. p. 66 - 71. Retrieved 2016/07/06.