2',7'-Dichlorofluorescein Property

Melting point:

280 °C (dec.)(lit.)

Boiling point:

514.77°C (rough estimate)

Density 

0.79 g/mL at 20 °C

refractive index 

1.5300 (estimate)

Flash point:

12°C (53.6°F)

storage temp. 

room temp

solubility 

alcohol: passes test

form 

crystalline

pka

4.46(at 25℃)

color 

orange to red-brown, powder

PH Range

4.0 (colorless) - 6.6 (green)

Water Solubility 

Soluble in ethanol and methanol. Slightly dimethyl sulfoxide. Insoluble in water.

λmax

509nm

BRN 

58009

Stability:

Stable. Incompatible with strong oxidizing agents.

Major Application

Electroluminescent devices, sol-gel silica films, integrated circuits, photoresists, lithographic printing plates, recording material, LED devices, photoconductors, Solid-state dye laser, lithographic printing plates, inks, Fluorescent pH sensors, emissive probes, chemotherapeutic treatment of disease, phototherapeutic treatment of disease, photodynamic treatment of disease

InChIKey

NZVMJBGGAQSNLI-UHFFFAOYSA-N

CAS DataBase Reference

76-54-0(CAS DataBase Reference)

EPA Substance Registry System

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 2',7'-dichloro-3',6'-dihydroxy- (76-54-0)

Safety

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-36-67-11

Safety Statements 

26-36-16

RIDADR 

UN 1219 3/PG 2

WGK Germany 

3

RTECS 

NT8050000

TSCA 

Yes

HS Code 

3204 19 00

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

2',7'-Dichlorofluorescein Chemical Properties,Usage,Production

Note

Hans et al. report that 2',7'-Dichlorofluorescein (DCF) finds legitimate experimental use in the generation of standard curves used to calibrate DCFH2-DA experimental results, post-chromatography estimation of carbohydrates and in indirect fluorimetric detection in open tubular capillary chromatography (OTC-HPLC). However, DCF is inappropriate for demonstrating ROS as it is oxidized to a non-fluorescent compound in the presence of hydroxyl radicles[1].

Chemical Properties

red to yellow solid

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.

Uses

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.

Uses

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.

Definition

2',7'-dichlorofluorescein is a member of 2-benzofurans. It has a role as a fluorochrome. It derives from a fluorescin.

Application

2',7'-dichlorofluorescein has been used as an oxidation-sensitive fluorescent probe to measure ROS (reactive oxygen species) formation in cells.

Biological Activity

2',7'-dichlorofluorescein is an oxidation-sensitive fluorescent probe. 2′7′-dichlorofluorescein diacetate is oxidized to 2′7′-dichlorofluorescein in the presence of ROS (reactive oxygen species).

Biochem/physiol Actions

2′,7′-Dichlorofluorescein is an oxidation-sensitive fluorescent probe. 2′7′-dichlorofluorescein diacetate is oxidized to 2′7′-dichlorofluorescein in the presence of ROS (reactive oxygen species).

References

[1] Chander Hans. “2’,7’-Dichlorofluorescein (DCF) or 2’,7’-dichlorodihydrofluorescein diacetate (DCFH2-DA) to measure reactive oxygen species in erythrocytes.” Biomedicine & Pharmacotherapy (2021): 111512.