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Fluorescein diacetate

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Name

Fluorescein diacetate

EINECS 209-877-6
CAS No. 596-09-8 Density 1.47 g/cm3
PSA 88.13000 LogP 4.10520
Solubility Soluble in chloroform, DMSO, ethanol, and water. Melting Point 200-203 °C(lit.)
Formula C24H16O7 Boiling Point 604.7 °C at 760 mmHg
Molecular Weight 416.387 Flash Point 264 °C
Transport Information N/A Appearance Light yellow powder
Safety 24/25-36/37/39-27-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 596-09-8 (FLUORESCEIN DIACETATE) Hazard Symbols IrritantXi
Synonyms

Fluorescein,diacetate (6CI,7CI,8CI);3',6'-Diacetylfluorescein;F 1303;FDA;Fluorescein 3',6'-diacetate;MFCD 5062;NSC 4726;NSC 667259;

Article Data 16

Fluorescein diacetate Synthetic route

64-19-7

acetic acid

2321-07-5

fluorescein

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With phosphorus pentoxide at 60℃; for 2h; solid phase reaction;94%
108-24-7

acetic anhydride

2321-07-5

fluorescein

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2.5h;91%
for 3 - 5h; Heating / reflux;75%
Reflux;72.6%
75-36-5

acetyl chloride

2321-07-5

fluorescein

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With pyridine; acetic acid
With pyridine; dmap In dichloromethane for 1h;
2321-07-5

fluorescein

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With sodium acetate; acetic anhydride
With sulfuric acid; acetic anhydride
With Ketene; acetone
With acetic anhydride
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

620960-03-4

5-bromofluorescein diacetate

A

596-09-8

fluorescein diacetate

B

649734-78-1

C30H27BO9

Conditions
ConditionsYield
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); triethylamine In 1,4-dioxane at 80℃; for 20h;
620960-03-4

5-bromofluorescein diacetate

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; H-BO2C6H12; triethylamine In 1,4-dioxane at 80℃; for 20h;
85-44-9

phthalic anhydride

activated aluminium

activated aluminium

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 195 - 200 °C
View Scheme
Multi-step reaction with 2 steps
1: concentrated sulfuric acid
2: pyridine; glacial acetic acid
View Scheme
2513-33-9

2-(2,4-dihydroxybenzoyl)benzoic acid

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: beim Erhitzen ueber den Schmelzpunkt
View Scheme
108-46-3

recorcinol

phenoldiazonium chloride-(4)

phenoldiazonium chloride-(4)

596-09-8

fluorescein diacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 195 - 200 °C
View Scheme
596-09-8

fluorescein diacetate

2321-07-5

fluorescein

Conditions
ConditionsYield
Stage #1: fluorescein diacetate With sodium hydroxide In methanol; water for 1.5h; Heating / reflux;
Stage #2: With hydrogenchloride In ethanol; water at 20 - 25℃; for 1h; pH=1 - 2.5;
80%
With water In acetonitrile pH=4.8; aq. acetate buffer;
With porcine liver carboxylesterase In 2-methoxy-ethanol; water at 37℃; for 0.5h; pH=8; Enzymatic reaction;

Fluorescein diacetate Specification

The Fluorescein diacetate ,its cas register number is 596-09-8.It also can be called as 3-Oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-3',6'-diyl diacetate and the IUPAC name about this chemicals is (6'-Acetyloxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) acetate .It belongs to the following product categories, such as Colours, Dyes, Indicators & Pigments and so on.It can be stored under 20°C.

Following are the chemical properties about Fluorescein diacetate :(1)#H bond acceptors: 7 ; (2)#H bond donors: 0 ; (3)#Freely Rotating Bonds: 4 ; (4)Polar Surface Area: 88.13Å2 ; (5)Index of Refraction: 1.681 ; (6)Molar Refractivity: 107.16 cm3 ; (7)Molar Volume: 283.1 cm3 ; (8)Polarizability: 42.48x10-24cm3 ; (9)Surface Tension: 69.2 dyne/cm; (10)Enthalpy of Vaporization: 89.92 kJ/mol ; (11)Vapour Pressure: 1.42E-14 mmHg at 25°C

It is a dangerous chemical, because it irritating to eyes, respiratory system and skin. In the using process, you need to wear suitable protective clothing, gloves and eye/face protection and avoid contact with skin and eyes, also take off immediately all contaminated clothing, In addition, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. WGK Germany about this chemical is 3.

The Fluorescein diacetate is a light yellow powder, it also known as FDA, it can be used as fluorescein through the cell membrane to accumulate in living cells, As the hydrophilic of fluorescent is lower than BCECF or calcein, fluorescein leakage from the cell volume was also high.FDA is also used for flow cytometry. Fluorescence excitation and emission wavelengths were 488nm and 530nm.

This chemicals can be described computed from structure:
(1)Canonical SMILES: CC(=O)OC1=CC2=C(C=C1)C3(C4=C(O2)C=C(C=C4)OC(=O)C)C5=CC=CC=C5C(=O)O3
(2)InChI: InChI=1S/C24H16O7/c1-13(25)28-15-7-9-19-21(11-15)30-22-12-16(29-14(2)26)8-10-20(22)24(19)18-6-4-3-5-17(18)23(27)31-24/h3-12H,1-2H3
(3)InChIKey: CHADEQDQBURGHL-UHFFFAOYSA-N

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