Basic information
- CAS
76-54-0- Standard SMILES
O=C1OC2(c3cc(Cl)c(O)cc3Oc3cc(O)c(Cl)cc32)c2ccccc21- InChIKey
VFNKZQNIXUFLBC-UHFFFAOYSA-N- Molecular formula
- C20H10Cl2O5
- Average molar mass
- 401.2 g/mol
- Monoisotopic mass
- 399.9905288
Overview
2',7'-dichlorofluorescein is a member of 2-benzofurans. It has a role as a fluorochrome. It is functionally related to a fluorescin.
Names & identifiers
- Preferred name
- 2',7'-Dichlorofluorescein
- IUPAC
- 2',7'-dichloro-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
- English name
- 2',7'-Dichlorofluorescein
- Molecular formula
- C20H10Cl2O5
- Molecular weight
- 401.2
Names & synonyms
2',7'-Dichlorofluorescein76-54-0Fluorescein 27FLUORESCEIN 5482',7'-dichlorofluorescin56NQM5UZT1D AND C ORANGE 25DTXSID8058798FLUORESCEIN-27FLUORESCEIN-548D AND C ORANGE-25CHEBI:51596
Show more names
DICHLOROFLUORESCEINDCDHF3,6-DICHLOROFLUORAN2,7-DichorofluorescinFLUORESCEIN DICHLORIDEDICHLOROFLUORESCEIN TS
Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 2',7'-dichloro-3',6'-dihydroxy-Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 2',7'-dichloro-3',6'-dihydroxy-RefChem:80172DTXCID4047830200-968-62,7-Dichlorofluorescein2',7'-Dichloro-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-oneMFCD00005047
Database identifiers
- CAS
76-54-0- PubChem CID
- 64944
- DTXSID
DTXSID8058798- ChEMBL
CHEMBL1908059- ChEBI
CHEBI:51596
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 585
Experimental & physicochemical properties
Chemical ClassesDyes -> Other Dyes
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- 280 °C · 280 °C (dec.)(lit.)
- Boiling point
- 514.77 °C · 514.77°C (rough estimate)
- Density
- 0.79 g/mL · 0.79 g/mL at 20 °C
- bulk density
- 390 kg/m3 · 390kg/m3
- refractive index
- 1.53 · 1.5300 (estimate)
- Flash point
- 12 °C · 12°C (53.6°F)
- storage temp.
- room temp
- solubility
- alcohol: passes test
- form
- crystalline
- pka
- 4.46 · 4.46(at 25℃)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 2.1% (1 of 47) of reports.
Warning
H315 (87.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 2',7'-dichloro-3',6'-dihydroxy-
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 2',7'-dichloro-3',6'-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Sigma-Aldrich MSDS] See Fluorescein.
Hazard Classes and CategoriesSkin Irrit. 2 (87.2%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NT8050000
- ridadr
- UN 1219 3/PG 2
- hs_code
- 3204 19 00
- risk_code
- 36/37/38-36-67-11
- Signal word
- Warning
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 2',7'-dichloro-3',6'-dihydroxy-: ACTIVE
Applications
Description2',7'-Dichlorofluorescein can be used in the synthesis of 2',7'-Dichlorodihydrofluorescein, which is a cell-permeable non-fluorescent probe.
UsesWidely 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.
Uses2',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.
Uses2',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.
Upstream & downstream products
Upstream raw materials
Related reactions
2 records
Compound notes
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