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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
6-Aminofluorescein is a building block for synthesis of fluorescein and a reagent for fluorescence studies.
Synonyms: 6-Aminofluorescein
4.5
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| CAS No. : | 51649-83-3 |
| Formula : | C20H13NO5 |
| M.W : | 347.32 |
| SMILES Code : | O=C1OC2(C3=C(OC4=C2C=CC(O)=C4)C=C(O)C=C3)C5=C1C=CC(N)=C5 |
| Synonyms : |
6-Aminofluorescein
|
| English Name : | 6-Amino-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one |
| MDL No. : | MFCD00005051 |
| InChI Key : | YOAWSYSKQHLFPM-UHFFFAOYSA-N |
| Pubchem ID : | 103924 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ethanol; nickel Hydrogenation; | ||
| With palladium-on-charcoal; hydrazine hydrate |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In <i>N</i>-methyl-acetamide; triethylamine | 8 7,8-Dihydromorphine-3-(fluorescein-6-ylamino-carbonylmethyl) Ether EXAMPLE 8 7,8-Dihydromorphine-3-(fluorescein-6-ylamino-carbonylmethyl) Ether 7,8-Dihydromorphine-3-carboxymethyl ether hydrochloride (0.1 mmol) was dissolved in 0.3 ml of dimethylformamide. The solution was cooled in an ice bath and 0.014 ml triethylamine and 0.0105 ml of ethyl chloroformate were added. The solution was stirred for 11/2 hours, and half of it was allowed to react with 6-aminofluorescein at room temperature overnight. The product was purified by chromatography on a silica gel thin layer plate, developing with chloroform/methanol/acetic acid, then on a second plate developed with chloroform/methanol. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 75% | Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride; sodium nitrite In water for 0.333333h; Stage #2: With sodium azide In water at 0℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 350 mg | With calcium carbonate In acetone at 20℃; for 3h; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85% | In acetone at 0 - 20℃; for 3h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 88% | In ethanol for 4h; Reflux; | 2.4.1 General synthesis General procedure: 7-Amino-4-methyl-coumarin (B) (0.040g, 2.28×10-4mol) or 6-Aminofluorescein (C) (0.080g, 2.30×10-4mol) was dissolved in absolute ethanol, followed by the addition of pyridoxal-5′-phosphate (A) (0.056g, 2.28×10-4mol; 0.057g, 2.30×10-4mol). The solution was stirred and kept under refluxing for 4h. At the end, light orange (compound 1) and orange (compound 2) powders were obtained, and were washed several times with cold ethanol, diethylether and dried under vacuum. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 39% | Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With sodium hydrogencarbonate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: 2-Bromoacetyl bromide In tetrahydrofuran for 0.25h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 6'-amino-3,6-dihydroxyspiro<xanthene-9,1'-isobenzofuran>-3'-one With hydrogenchloride In water Stage #2: With sodium nitrite In water for 0.00277778h; Cooling with ice; | Preparation of fluorescein-diazonium (7): 6-aminofluorescein was dissolved in 10 mM MCl at a concentration of 10 mM. Separately a 60 mM sodium nitrite solution was prepared and both solutions were cooled on ice. 20 μL NaNO2 (60 mM) was added to 100 μL of fluorescein (10 mM) and vortexed for 10 sec then kept on ice to generate a 8.3 mM fluorescein diazonium solution. This solution was further diluted to 1 mM with water and used for the labeling studies. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With caesium carbonate In acetonitrile at 20℃; for 0.5h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide In dimethyl sulfoxide at 25℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 5-chloro-pentanal; 5′-aminofluorescein With sodium cyanotrihydridoborate In N,N-dimethyl acetamide at 20℃; for 1h; Stage #2: acetaldehyde With sodium cyanotrihydridoborate In N,N-dimethyl acetamide Stage #3: Cysteamine In methanol; N,N-dimethyl acetamide; lithium hydroxide monohydrate | 1 Synthesis of 6-NDS-CA (0154) To a solution of 1 eq. of 6-aminofluorescein in DMAC a solution of 1.1 eq. of 5- chloropentanal in DMAC was added. The mixture was stirred for 5 min at room temperature and then 2eq. of sodium cyanoborohydride was added. The mixture was stirred for 1 h. NMR spectra showed that the reaction was completed. After that, to the reaction mixture 15eq. of acetaldehyde was added, followed by 2.5eq. of sodium triacetoxyborohydride. The conversion of the reaction was controlled by NMR. Next, to the resulting reaction mixture 10eq. of cysteamine was added in MeOH-water solution. The resulting mixture then was transferred to a falcon tube and distilled water was added to precipitate the crude product, which was separated by centrifugation. Next, 7 ml of water was added to the separated precipitate and the resulting suspension sonicated for 2 minutes. The procedure was repeated 5 times and the purity of the product was controlled by NMR |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 52 % | With Sodium thiosulfate pentahydrate; 1,2-Diiodoethane; potassium nitrate In acetonitrile Reflux; Sealed tube; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogenchloride; sodium nitrite In water at 0℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91 % | With water-d2; trityl tetrakis(pentafluorophenyl)borate In 1,2-dichloro-ethane at 90℃; Schlenk technique; Inert atmosphere; | 30 Embodiment 30: Take a clean and dry 25mL Schlenk tube, equip it with a magnetic stirring rotor of appropriate size, and accurately weigh and add Ph3C+[B(C6F5)4]-(18.4mg,0.02mmol,0.1equiv.), D2O (200uL, 55equiv.) and substrate (0.2mmol, 1.0equiv.). Then, the pump was drained, vacuumed, and backfilled with argon, repeated 3 times, and then 1.0mL of dichloroethane was injected into the syringe. Then, the Schlenk tube was transferred to a 90°C oil bath for heating, and the reaction was stirred rapidly for 10h. After the reaction was completed, TLC was used to detect the reaction situation, 2mL of DCM was added to dilute the reaction solution, filtered through a thin layer of silica gel column, and washed with 10mL of DCM. The filtrate was concentrated under reduced pressure, the organic solvent was concentrated under reduced pressure, and purified by silica gel column chromatography to obtain the target compound.6-amino-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one-2',4',5,5',7,7'-d6(30) |
| 91% | With water-d2; trityl tetrakis(pentafluorophenyl)borate In dimethyl sulfoxide; 1,2-dichloro-ethane at 100℃; Schlenk technique; Sealed tube; Inert atmosphere; |