2',7'-Dichlorofluorescein

Base Information

• Chemical Name: 2',7'-Dichlorofluorescein
• CAS No.: 76-54-0
• Deprecated CAS: 116189-73-2,153474-60-3,87714-38-3,1529808-38-5,153474-60-3,87714-38-3
• Molecular Formula: C20H10Cl2O5
• Molecular Weight: 401.202
• Hs Code.: 3204 19 00
• European Community (EC) Number: 200-968-6
• UNII: 56NQM5UZT1
• DSSTox Substance ID: DTXSID8058798
• Nikkaji Number: J192.556C
• Wikipedia: Dichlorofluorescein
• Wikidata: Q209286
• ChEMBL ID: CHEMBL1908059
• Mol file: 76-54-0.mol

Synonyms:2',7'-dichlorofluorescein;2',7'-dichlorofluorescein, disodium salt;2',7'-dichlorofluorescin;dichlorofluorescin;monohlorofluorescein

Chemical Property of 2',7'-Dichlorofluorescein

Chemical Property:

• Appearance/Colour: orange-yellow Solid
• Melting Point: 280 °C (dec.)(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 634.4 °C at 760 mmHg
• PKA: 4.46(at 25℃)
• Flash Point: 337.4 °C
• PSA: 75.99000
• Density: 0.79 g/mL at 20 °C
• LogP: 4.97260
• Storage Temp.: Store at +5°C to +30°C.
• Solubility.: alcohol: passes test
• Water Solubility.: Soluble in ethanol and methanol. Slightly dimethyl sulfoxide. Insoluble in water.
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 399.9905288
• Heavy Atom Count: 27
• Complexity: 585

Purity/Quality:

98%,99%, ^*data from raw suppliers

2'',7''-Dichlorofluorescein ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,F
• Statements: 36/37/38-36-67-11
• Safety Statements: 26-36-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C=C4OC5=CC(=C(C=C35)Cl)O)O)Cl
• Uses: Widely used probe, e.g. for determination of carbohydrates by fluorescence densitometry after TLC and determination of H2O2 by chemiluminescence. Fluorescent additives used in indirect fluorimetric detection in OTC-HPLC. 2',7'-Dichlorofluorescein is used as an indicator and as a cellular antioxidant activity. It is also used for the determination of carbohydrates and hydrogen peroxide by fluorescence densitometry and chemiluminescence respectively. It is used as an indicator for argentometry by Fajans method. It is also involved in the cellular antioxidant activity assay. It is utilized as an additive in fluorescence and laser studies.A new fluorescent sensor for Cd2+ and its application in living cells imaging. Tetrahedron Lett. 2015, 56 (11), 1322-1327.Colorimetric and fluorogenic signaling of fluoride ions by thiophosphinated dichlorofluorescein. Dyes Pigm. 2015, 112, 170-175. 2',7'-Dichlorofluorescein is used as an indicator and as a cellular antioxidant activity. It is also used for the determination of carbohydrates and hydrogen peroxide by fluorescence densitometry and chemiluminescence respectively. It is used as an indicator for argentometry by Fajans method. It is also involved in the cellular antioxidant activity assay. It is utilized as an additive in fluorescence and laser studies.

Technology Process of 2',7'-Dichlorofluorescein

There total 7 articles about 2',7'-Dichlorofluorescein 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: 90.0%

phthalic anhydride (85-44-9) + 4-Chlororesorcinol (95-88-5) → 2',7'-dichlorofluorescein (76-54-0)

Guidance literature:

In methanesulfonic acid; at 90 ℃; for 24h;

DOI:10.1021/acs.joc.7b00285

Reference yield:

fluorescein free acid (518-45-6) → 2',7'-dichlorofluorescein (76-54-0)

Guidance literature:

fluorescein free acid; With phosphorus pentachloride; In chlorobenzene; at 140 ℃; for 6h; Heating / reflux;

With 1-methyl-pyrrolidin-2-one; at 100 ℃;

Reference yield:

2-(3,6-diacetyloxy-2,7-dichloro-9H-xanthen-9-yl)benzoic acid (4091-99-0) → 2',7'-dichlorofluorescein (76-54-0)

Guidance literature:

With hemin; d(ATTGTGCGTCATCCCTTACGTCAGTGGAG), screened from Cauliflower mosaic virus (CaMV) 35S promoter; d(CTCCACTGACGTAATGGGTAGGG); d(GGGTTGGGCGGATGACGCACAAT); potassium chloride; ammonium acetate; In water; at 20 ℃; for 0.166667h; pH=7; aq. buffer;

DOI:10.1039/c0cc02933e

upstream raw materials:

phthalic anhydride

4-Chlororesorcinol

benzene-1,2-dicarboxylic acid

recorcinol

Downstream raw materials:

2',7'-dichlorodihydrofluorescein diacetate

2',7'-dichlorofluorescein ethoxycarbonylmethyl ester ethoxycarbonylmethyl ether

9-(o-carboxyphenyl)-2,7-dichloro-4,5-bis[bis(2-pyridylmethyl)-aminomethyl]-6-hydroxy-3-xanthanone

2-(2,7-dichloro-3,6-dihydroxy-9H-xanthen-9-yl)benzoic acid

Refernces

• 1、 Khatun, Mahamuda,Choudhury, Susobhan,Liu, Bo,Lemmens, Peter,Pal, Samir Kumar,Mazumder, Santasree. "Resveratrol-ZnO nanohybrid enhanced anti-cancerous effect in ovarian cancer cells through ROS". . p. 105607 - 105617. Retrieved 2016.
• 2、 Liu, Yanan,Zhang, Xiaonian,Zhang, Rong,Chen, Tianfeng,Wong, Yum-Shing,Liu, Jie,Zheng, Wen-Jie. "Ruthenium-porphyrin complexes induce apoptosis by inhibiting the generation of intracellular reactive oxygen species in the human hepatoma cell line (HepG2)". . p. 1974 - 1980. Retrieved 2011.
• 3、 Braeutigam, Patrick,Buchheim, Johannes R.,Neumeister, Peter,Raufeisen, Sascha,Stelter, Michael. "Pyrocatalytic oxidation-strong size-dependent poling effect on catalytic activity of pyroelectric BaTiO3nano- And microparticles". . p. 23464 - 23473. Retrieved 2020/11/18.
• 4、 Jadhav, Nirajkumar H.,Shinde, Dnyaneshwar R.,Sakate, Sachin S.,Rasal, Nishant K.,Pawar, Ramdas A.. "Ti(IV) doping: An effective strategy to boost Lewis acidic performance of ZnO catalyst in fluorescein dye synthesis". . p. 17 - 22. Retrieved 2018/11/25.