15086-94-9

Basic information

• Product Name: Solvent Red 43
• Synonyms: BROMO ACID J;BROMO ACID J TS, XL, OR XX;BROMOFLUORESCEIN;BRONZE BROMO ES;EOSIN Y;EOSIN Y DISODIUM SALT;EOSIN YELLOWISH WATER-SOLUBLE;EOSIN YELLOWISH Y
• CAS NO: 15086-94-9
• Molecular Formula: C₂₀H₈Br₄O₅
• Molecular Weight: 647.89
• EINECS: 241-409-6
• Product Categories: Organics;marker
• Mol File: 15086-94-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 640.3 °C at 760 mmHg
• Flash Point: 341 °C
• Appearance: /Liquid
• Density: 1.02 g/mL at 20 °C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: 0.1 g/mL, dark red
• PKA: 6.97±0.20(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Solvent Red 43(CAS DataBase Reference)
• NIST Chemistry Reference: Solvent Red 43(15086-94-9)
• EPA Substance Registry System: Solvent Red 43(15086-94-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• RTECS: LM5850000
• Hazardous Substances Data: 15086-94-9(Hazardous Substances Data)

Usage

Uses

Eosin Acid C.I. No. 45380 (CAS# 15086-94-9) is a photo-senseitive organic catalyst and has been used in the photocatalytic, diastereoselective additions of 1-sulfoximidoyl-1,2-benziodoxoles to styrenes, and in the stereoselective synthesis of 2-deoxyglycosides from glycals. Dyes and metabolites.

Preparation

Fluorescein (C.I. Acid Yellow 73, C.I. 45350) in water or ethanol solution bromide into four bromine derivatives, And made into a free acid form..

Properties and Applications

brilliant yellow red. Soluble in water and ethanol for blue light red, with yellow green fluorescence. In concentrated sulfuric acid to yellow, dilution after yellow red precipitation.

InChI:InChI=1/C20H10Br4O5/c21-11-5-9-13(7-3-1-2-4-8(7)20(27)28)10-6-12(22)17(26)15(24)19(10)29-18(9)14(23)16(11)25/h1-6,13,25-26H,(H,27,28)

Synthetic route

fluorescein (2321-07-5) → eosin y (15086-94-9)

Conditions	Yield
With Oxone; sodium bromide at 200℃; for 12h;	100%
With sodium hypochlorite; hydrogen bromide; sodium sulfite In 2-methyltetrahydrofuran; water at 20℃; for 3h; Flow reactor;	78%
With ethanol; bromine

fluorescein disodium salt (518-47-8) → eosin y (15086-94-9)

Conditions	Yield
With N-Bromosuccinimide In ethanol at 20℃; for 0.5h;	89%

phthalic anhydride (85-44-9) + 2,4-dibromo-1,3-benzenediol (18011-67-1) → eosin y (15086-94-9)

Conditions	Yield
With zinc(II) chloride

3,5-dibromo-2'-carboxy-2,4-dihydroxybenzophenone (3341-06-8) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → phthalic anhydride (85-44-9) + eosin y (15086-94-9)

Conditions	Yield
at 230 - 240℃;

3,5-dibromo-2'-carboxy-2,4-dihydroxybenzophenone (3341-06-8) → phthalic anhydride (85-44-9) + eosin y (15086-94-9)

Conditions	Yield
With zinc(II) chloride at 235 - 240℃; im Wasserstoffstrom;

3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one (596-28-1) + 3,5-dibromo-4-hydroxysalicylic acid (3147-46-4) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → eosin y (15086-94-9)

Conditions	Yield
at 170℃;

eosine (152-75-0) → eosin y (15086-94-9)

Conditions	Yield
In 1,4-dioxane Equilibrium constant; Investigation of the effect of various organic solvents.;

fluorescein sodium salt (518-47-8) → eosin y (15086-94-9)

Conditions	Yield
With potassium bromate; sulfuric acid; potassium bromide In water; acetone for 2h;	1.15 g

sulfuric acid (7664-93-9) + Eosin ethyl ester (26799-78-0) → eosin y (15086-94-9)

Conditions	Yield
at 150℃;

ethanol (64-17-5) + fluorescein (2321-07-5) + bromine (4 mol) → eosin y (15086-94-9)

acetic acid (64-19-7) + fluorescein (2321-07-5) + bromine (4 mol) → eosin y (15086-94-9)

3,5-dibromo-4-hydroxysalicylic acid (3147-46-4) + pyrocatecholphthalein → eosin y (15086-94-9)

Conditions	Yield
With zinc(II) chloride at 170℃;

2,4-dibromo-1,3-benzenediol (18011-67-1) + ZnCl2 → phthalic anhydride (85-44-9) + eosin y (15086-94-9)

3,5-dibromo-4-hydroxysalicylic acid (3147-46-4) + pyrocatecholphthalein + ZnCl2 → eosin y (15086-94-9)

Conditions	Yield
at 170℃;

phthalic anhydride (85-44-9) + activated aluminium → eosin y (15086-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc chloride 2: glacial acetic acid; bromine View Scheme
Multi-step reaction with 2 steps 1: 195 - 200 °C 2: glacial acetic acid; bromine View Scheme

2-(2,4-dihydroxybenzoyl)benzoic acid (2513-33-9) → eosin y (15086-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: beim Erhitzen ueber den Schmelzpunkt 2: glacial acetic acid; bromine View Scheme
Multi-step reaction with 2 steps 2: glacial acetic acid; bromine View Scheme

3,5-dibromo-4-hydroxysalicylic acid (3147-46-4) → eosin y (15086-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: zinc chloride View Scheme

recorcinol (108-46-3) + phenoldiazonium chloride-(4) → eosin y (15086-94-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc chloride 2: glacial acetic acid; bromine View Scheme
Multi-step reaction with 2 steps 2: glacial acetic acid; bromine View Scheme
Multi-step reaction with 2 steps 1: 195 - 200 °C 2: glacial acetic acid; bromine View Scheme

Eosin Y (548-26-5, 602-47-1, 17372-87-1) → eosin y (15086-94-9)

Conditions	Yield
With hydrogenchloride; aluminum oxide for 3h;

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2) + eosin y (15086-94-9) → C8H10N4O2*2H2O*C20H8Br4O5

Conditions	Yield
In ethanol; water for 0.5h;	70%

6-monodeoxy-6-monoamino-β-cyclodextrin hydrochloride + eosin y (15086-94-9) → C62H76Br4NO38(1-)*Na(1+)

Conditions	Yield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In water at 20℃; for 3h;	67%

eosin y (15086-94-9) → eosin Y barium(II) salt

Conditions	Yield
With barium hydroxide octahydrate In water at 20℃; for 0.166667h; Sonication;	51%

1,4-dibromo-butane (110-52-1) + eosin y (15086-94-9) → C28H22Br6O5

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 24h; Inert atmosphere;	50%

eosin y (15086-94-9) → eosin Y copper(II) salt

Conditions	Yield
Stage #1: eosin y In water at 20℃; for 0.166667h; Sonication; Stage #2: With copper(II) acetate monohydrate In water at 20℃; for 12h;	38%

acetyl chloride (75-36-5) + eosin y (15086-94-9) → (6'-acetoxy-2′,4′,5′,7′-tetrabromo-3-oxo-spiro[isobenzofuran-1,9′-xanthene]-3′-yl) acetate (7284-92-6)

Conditions	Yield
With pyridine; dmap In dichloromethane for 1h;	37%

eosin y (15086-94-9) → eosin Y silver(I) salt

Conditions	Yield
Stage #1: eosin y In water at 20℃; for 0.166667h; Sonication; Stage #2: With silver(I) acetate In water at 20℃; for 12h;	32%

eosin y (15086-94-9) → eosin Y lead(II) salt

Conditions	Yield
Stage #1: eosin y In water at 20℃; for 0.166667h; Sonication; Stage #2: With lead acetate In water at 20℃; for 12h;	16%

eosin y (15086-94-9) → eosin Y gadolinium(III) salt

Conditions	Yield
Stage #1: eosin y In water at 20℃; for 0.166667h; Sonication; Stage #2: With gadolinium(III) acetate trihydrate In water at 20℃; for 12h;	12%

methanol (67-56-1) + eosin y (15086-94-9) → 2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid methyl ester (127424-71-9)

Conditions	Yield
With sulfuric acid
With sulfuric acid

ethanol (64-17-5) + 3α,12α-dihydroxy-5β-chol-8(14)-en-24-oic acid (641-81-6) + eosin y (15086-94-9) → 3α,12α-dihydroxy-5β-chol-14-en-24-oic acid

Conditions	Yield
Einwirkung von Sonnenlicht;

ethanol (64-17-5) + eosin y (15086-94-9) → Eosin ethyl ester (26799-78-0)

Conditions	Yield
With sulfuric acid

acetic anhydride (108-24-7) + eosin y (15086-94-9) → (6'-acetoxy-2′,4′,5′,7′-tetrabromo-3-oxo-spiro[isobenzofuran-1,9′-xanthene]-3′-yl) acetate (7284-92-6)

Conditions	Yield
at 140℃;
for 5h; Reflux;

2-oxo-propionic acid (127-17-3) + eosin y (15086-94-9) → oxalic acid (144-62-7)

Conditions	Yield
Irradiation;

BIGUANIDE (56-03-1) + eosin y (15086-94-9) → 2,4,5,7-tetrabromo-9-[2-(diamino-[1,3,5]triazin-2-yl)-phenyl]-6-hydroxy-xanthen-3-one

aniline (62-53-3) + eosin y (15086-94-9) → 2',3',4',5',6',7'-hexaanilino-spiro[phthalan-1,9'-xanthen]-3-one

Conditions	Yield
at 180 - 200℃;

ethanol (64-17-5) + cholestadiene-(5.7) (7631-33-6) + eosin y (15086-94-9) + benzene (71-43-2) → bi-(cholestadien-(5.8)-yl)-(7ξ.7'ξ)

Conditions	Yield
Sonnenlicht, unter CO2.Irradiation;

eosin y (15086-94-9) → 2',7'-dibromo-3',6'-dihydroxy-spiro[phthalan-1,9'-xanthen]-3-one (25709-81-3)

Conditions	Yield
With 1,4-dioxane; hydrogenchloride; acetic acid Reagens 4: Zinn(II)-chlorid;

eosin y (15086-94-9) → 2',4',5',7'-tetrabromo-3',6'-dichloro-spiro[phthalan-1,9'-xanthen]-3-one (124521-79-5)

Conditions	Yield
With phosphorus pentachloride at 100℃;

eosin y (15086-94-9) → 2,7-dinitro-4,5-dibromofluorescein (56360-46-4)

Conditions	Yield
With ethanol; nitric acid

eosin y (15086-94-9) → eosine (152-75-0)

Conditions	Yield
In 1,4-dioxane Equilibrium constant; Investigation of the effect of various organic solvents.;

Upstream product

• 2321-07-5 fluorescein 
• 518-47-8 fluorescein sodium salt 
• 7664-93-9 sulfuric acid 
• 26799-78-0 Eosin ethyl ester 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 3147-46-4 3,5-dibromo-4-hydroxysalicylic acid 
• 18011-67-1 2,4-dibromo-1,3-benzenediol 
• 518-47-8 fluorescein disodium salt 
• 108-46-3 recorcinol 
• 2513-33-9 2-(2,4-dihydroxybenzoyl)benzoic acid 
• 85-44-9 phthalic anhydride 
• 152-75-0 eosine 
• 596-28-1 3,3-bis-(3,4-dihydroxy-phenyl)-3H-isobenzofuran-1-one 

Downstream Products

• 127424-71-9 2-(2,4,5,7-tetrabromo-6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid methyl ester 
• 26799-78-0 Eosin ethyl ester 
• 7284-92-6 eosin Y diacetate 
• 144-62-7 oxalic acid 
• 25709-81-3 2',7'-dibromo-3',6'-dihydroxy-spiro[phthalan-1,9'-xanthen]-3-one 
• 56360-46-4 2,7-dinitro-4,5-dibromofluorescein 
• 110-17-8 (2E)-but-2-enedioic acid 
• 512-85-6 ascaridole 
• 2321-07-5 fluorescein 
• 463-79-6 carbonic-acid 
• 10035-10-6 hydrogen bromide 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 34085-09-1 1,5-dihydro-5-hydroxy-2H-pyrrol-2-one 
• 152-75-0 eosine 

Relevant articles and documents

Novel β-cyclodextrin-eosin conjugates

Eosin B (EoB) and eosin Y (EoY), two xanthene dye derivatives with photosensitizing ability were prepared in high purity through an improved synthetic route. The dyes were grafted to a 6-monoamino-β-cyclodextrin scaffold under mild reaction conditions through a stable amide linkage using the coupling agent 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride. The molecular conjugates, well soluble in aqueous medium, were extensively characterized by 1D and 2D NMR spectroscopy and mass spectrometry. Preliminary spectroscopic investigations showed that the β-cyclodextrin-EoY conjugate retains both the fluorescence properties and the capability to photogenerate singlet oxygen of the unbound chromophore. In contrast, the corresponding β-cyclodextrin-EoB conjugate did not show either relevant emission or photosensitizing activity probably due to aggregation in aqueous medium, which precludes any response to light excitation.

Electrophilic bromination in flow: A safe and sustainable alternative to the use of molecular bromine in batch

Bromination reactions are crucial in today’s chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br2) makes these brominations very challenging and hazardous. We describe here a safe and straightforward protocol for bromination in continuous flow. The hazardous Br2 or KOBr is generated in situ by reacting an oxidant (NaOCl) with HBr or KBr, respectively, which is directly coupled to the bromination reaction and a quench of residual bromine. This protocol was demonstrated by polybrominating both alkenes and aromatic substrates in a wide variety of solvents, with yields ranging from 78% to 99%. The protocol can easily be adapted for the bromination of other substrates in an academic and industrial environment.

Synthese d'eosine pure

According to solubilities of fluorescein and its brominated derivatives, pure eosin (2,4,5,7-tetrabromofluorescein) is prepared with a good yield (about 85 percent) by reaction of Br-/BrO3- on fluorescein in acidic water-acetone mixture.We have determined the exact composition of this medium which allows the precipitation of eosin while the other brominated derivatives of fluorescein remain soluble.