CAS No.2321-07-5,Fluorescein Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	2321-07-5
Name:	Fluorescein
Article Data:	103

Formula:	C₂₀H₁₂O₅
Molecular Weight:	332.312
Synonyms:	Fluorescein(8CI);3,6-Dihydroxyspiro[xanthene-9,3'-phthalide];3',6'-Fluorandiol;Benzoic acid,2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-;C.I. 45350:1;D and C Yellow No. 7;3',6'-Dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one;C Yellow No. 7;Japan Yellow 201;Japan Yellow No. 201;Resorcinolphthalein;Yellow fluorescein;
EINECS:	219-031-8
Density:	1.602 g/cm³
Melting Point:	314-316 °C
Boiling Point:	620.8 °C at 760 mmHg
Flash Point:	232.6 °C
Solubility:	Insoluble in water
Appearance:	orange-red crystalline powder
Hazard Symbols:	Xi
Risk Codes:	43-36/37/38
Safety:	22-24/25-26-36/37/39-27
PSA:	87.74000
LogP:	3.96860

Synthetic route

: 85-44-9
phthalic anhydride

: 108-46-3
recorcinol

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
In phosphoric acid for 0.00833333h; Microwave irradiation;	97%
With Zn0.95*Ti0.05O In neat (no solvent) at 160℃; for 1.33h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Green chemistry;	95%
With citric acid In toluene for 3h; Solvent; Reflux; Large scale;	94.8%

: 596-09-8
fluorescein diacetate

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
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;

: 3326-34-9
fluoresceinamine

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
With oxygen; nitrogen(II) oxide at 25℃; pH=7.4; Air; aq. HEPES buffer;	78.3%
With sodium acetate In chloroform; acetic anhydride; acetic acid

: 25932-69-8
2-<2,7-Dihydroxy-naphthoyl>-benzoesaeure

: 108-46-3
recorcinol

A: 582-17-2
2,7-Dihydroxynaphthalene

B: 2321-07-5
fluorescein

Conditions

Conditions	Yield
With methanesulfonic acid In toluene	A 43% B 20%

...Expand

: 85-44-9
phthalic anhydride

: 89-84-9
2',4'-dihydroxy-4-acetophenone

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
With sulfuric acid

: 85-44-9
phthalic anhydride

: 490-11-9
3,4-pyridinecarboxylic acid

: 108-46-3
recorcinol

: 2321-07-5
fluorescein

...Expand

: 85-44-9
phthalic anhydride

: 89-86-1
4-hydroxysalicylic acid

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
With zinc(II) chloride

: 85-44-9
phthalic anhydride

: 6409-58-1
1,3-dihydroxybenzene-4-sulfonic acid

: 2321-07-5
fluorescein

Conditions

Conditions	Yield
at 180℃;

: 85-44-9
phthalic anhydride

: 4,4'-bis-acetylamino-diphenic acid-anhydride

: 108-46-3
recorcinol

: 2321-07-5
fluorescein

...Expand

: 85-44-9
phthalic anhydride

: 6,6'-bis-acetylamino-diphenic acid-anhydride

: 108-46-3
recorcinol

: 2321-07-5
fluorescein

...Expand

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History

Fluorescein (CAS NO.2321-07-5) was first synthesized by Adolf von Baeyer in 1871.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one,3',6'-dihydroxy-, with the CAS registry number 2321-07-5, is also known as 3',6'-Dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one. It belongs to the product categories of E-F Fluorescent Probes, Labels, Particles and Stains; Fluorescein and Derivatives; Fluorescent Labels; Stains and Dyes; Aromatics; Fluorescent Labels & Indicators; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 219-031-8. This chemical's molecular formula is C₂₀H₁₂O₅ and molecular weight is 332.31. What's more, its systematic name is 3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthen]-3-one. Its classification codes are: (1)Coloring Agents; (2)Contrast media; (3)Diagnostic aid [corneal trauma indicator]; (4)Fluorescent Dyes; (5)Indicators and Reagents; (6)Luminescent Agents; (7)Mutation data. It is a phthalic indicator dye that appears yellow-green in normal tear film and bright green in a more alkaline medium, and is used therapeutically as a diagnostic aid in corneal injuries and corneal trauma. It has been approved by FDA for use in externally applied drugs and cosmetics. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one,3',6'-dihydroxy- are: (1)ACD/LogP: 2.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.682; (4)ACD/LogD (pH 7.4): 2.677; (5)ACD/BCF (pH 5.5): 64.328; (6)ACD/BCF (pH 7.4): 63.627; (7)ACD/KOC (pH 5.5): 685.565; (8)ACD/KOC (pH 7.4): 678.096; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 75.99 Å²; (13)Index of Refraction: 1.792; (14)Molar Refractivity: 87.995 cm³; (15)Molar Volume: 207.439 cm³; (16)Polarizability: 34.884×10^-24cm³; (17)Surface Tension: 90.403 dyne/cm; (18)Density: 1.602 g/cm³; (19)Flash Point: 232.645 °C; (20)Enthalpy of Vaporization: 95.37 kJ/mol; (21)Boiling Point: 620.841 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by phthalic acid anhydride and benzene-1,3-diol at the temperature of 160 °C. This reaction will need reagent conc. H₂SO₄ with the reaction time of 5 min. The yield is about 88%.

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one,3',6'-dihydroxy- can be prepared by phthalic acid anhydride and benzene-1,3-diol at the temperature of 160 °C

Uses of Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one,3',6'-dihydroxy-: it can be used to produce 2-(2,4-dihydroxy-benzoyl)-benzoic acid by heating. It will need reagent KOH and solvent H₂O with the reaction time of 5 hours. The yield is about 86%.

Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one,3',6'-dihydroxy- can be used to produce 2-(2,4-dihydroxy-benzoyl)-benzoic acid by heating

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin and may cause sensitisation by skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should take off immediately all contaminated clothing. You should not breathe dust. When using it, you must avoid contact with eyes and need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc2c(c1)C(=O)OC23c4ccc(cc4Oc5c3ccc(c5)O)O
(2)Std. InChI: InChI=1S/C20H12O5/c21-11-5-7-15-17(9-11)24-18-10-12(22)6-8-16(18)20(15)14-4-2-1-3-13(14)19(23)25-20/h1-10,21-22H
(3)Std. InChIKey: GNBHRKFJIUUOQI-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LDLo	unreported	400mg/kg (400mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
man	TDLo	intravenous	7143nL/kg (7143mL/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	American Journal of Ophthalmology. Vol. 126, Pg. 837, 1998.
mouse	LD50	intravenous	300mg/kg (300mg/kg)		United States Patent Document. Vol. #4775625.
mouse	LDLo	unreported	600mg/kg (600mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit	LDLo	intravenous	300mg/kg (300mg/kg)		International Journal of Leprosy and Other Mycobacterial Diseases. Vol. 2, Pg. 257, 1934.
rat	LDLo	intraperitoneal	600mg/kg (600mg/kg)		International Journal of Leprosy and Other Mycobacterial Diseases. Vol. 2, Pg. 257, 1934.