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CAS No. : | 6358-69-6 | MDL No. : | MFCD00037575 |
Formula : | C16H7Na3O10S3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KXXXUIKPSVVSAW-UHFFFAOYSA-K |
M.W : | 524.39 | Pubchem ID : | 61388 |
Synonyms : |
HPTS;Solvent Green 7;NSC 97285;Pyranine concentrated;Japan Green No. 204;Green No. 204;Green 204;D & C Green no. 8;8-Hydroxypyrene-1,3,6-trisulfonic Acid (sodium salt)
|
Num. heavy atoms : | 32 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 10.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 96.19 |
TPSA : | 216.97 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.85 cm/s |
Log Po/w (iLOGP) : | -41.03 |
Log Po/w (XLOGP3) : | 0.92 |
Log Po/w (WLOGP) : | 4.24 |
Log Po/w (MLOGP) : | 1.66 |
Log Po/w (SILICOS-IT) : | -0.7 |
Consensus Log Po/w : | -6.98 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.84 |
Solubility : | 0.0753 mg/ml ; 0.000144 mol/l |
Class : | Soluble |
Log S (Ali) : | -5.06 |
Solubility : | 0.00454 mg/ml ; 0.00000866 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.93 |
Solubility : | 0.0622 mg/ml ; 0.000119 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
245 g | With sodium hydroxide In water for 5 h; | In 2000 ml three-necked flask into 1200 grams of concentrated sulfuric acid, stirring into the 120 grams of flowers, a little warming to promoteAfter all the dissolved, slowly warming to 90 ° C for 1 hour, three bottles with a water bath to cool below 40 ° C, drop the liquid sulfur black 480 grams, 3 hours drop finished. And then to maintain the temperature of about 100 ° C reaction for 5 hours, down to room temperature, the three bottles of material into the 720 grams of ice water, into a sticky material, filter dry filter cake, get pyrene tetrasulfonic acid tetrasodium salt. And then the pyrene tetrasulfonic acid tetrasodium salt dissolved in 1000 ml of water into the 2000 ml three-necked flask, stirring with a plate of sodium hydroxide to neutral, then add 300 grams of flaky sodium hydroxide, slowly warming To micro-boiling state for 5 hours. After cooling, the first with hydrochloric acid and PH value of 7 or so, then add 100 grams of sodium chloride stirring dissolved, slowly precipitated light yellow solid, filtered and dried to get 8-hydroxy-1,3, 6-pyrene three Sodium sulfonate salt about 245 grams. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid; at 60℃; for 6h; | EXAMPLE 10 1-Hydroxy-3,6-dimethylsulfonamido-8-sulfonate-pyrene (Compound 14) [0143] 1-Hydroxy-trisulfonate-pyrene 13 (1 g, 1.9 mMol) was slowly added at room temperature to chlorosulfonic acid (10 ml). The mixture was then stirred at 60 C. for 6 hours and then carefully poured into ice. The resulting precipitate was filtered off and washed extensively with ice water. The brick red solid obtained was dried under vacuum for 30 minutes and then dissolved in acetone (50 ml). Dimethylamine (15 ml, 2M solution in THF) was added. The resulting solution was stirred for 3 hours and the concenrated under vacuum to give a dark brownish solid. Purification by silica gel column chromatography using CHCl3-MeOH (4:1) provided compound 14 (400 mg, 40%) as a yellow solid which was characterized by NMR and MS. %). 1H NMR (DMSO, 500 mHz): 2.79-2.80 (m, 12H), 8.34 (s, 1H), 8.76 (d, 1H), 8.80 (d, 1H), 8.92 (s, 1H), 8.93 (d, 1H), 8.43 (d, 1H); fluorescence (MeOH/H2O): lambda ex=490 nm, lambda em=545 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In methanol; | I. Methyl 1,3,6-trisulfo-8-pyrenyloxyacetate, trisodium salt (1) To a refluxing mixture of 26.2 g <strong>[6358-69-6]8-hydroxypyrene-1,3,6-trisulfonic acid, trisodium salt</strong> in 1.7 I. methanol, 29 g methyl 2-bromoacetate and 18 g diisopropylethylamine were added in three portions over five hours. After refluxing for an additional three hours, the mixture was allowed to cool, filtered and evaporated under reduced pressure. The crude product obtained from the filtrate was stirred in 500 ml isopropyl alcohol for 30 min. and collected by filtration. After drying over potassium hydroxide for two days under vacuum, 28.7 g light yellow powder was obtained. A sample of the dye was purified by chromatography over lipophilic Sephadex using water for elution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;Reactivity (does not react); | Coupling of Chlorocarbonylphenylboronic Anhydride with 8-Hydroxy-1,3,6-pyrenetrisulfonic Acid, Trisodium Salt. (Pyronin; D&C Green No.8) TLC shows a nonfluorescent spot at Rf=0.3 and a very fluorescent spot on the starting line. No product was isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | With sulfuric acid; In water; at 150℃; for 0.333333h;Product distribution / selectivity; | Referring to Scheme 4, a 50-mL round bottom flask equipped with a magnetic stirring bar was charged with HPTS (9.5 mmols, 5 g) and 30 % H2SO4 (35 mL). The mixture was heated at 150C for 20 min and then allowed to cool at ambient temp for 10 min. The solution was poured into 100 g of crushed ice and diluted to 200 mL with water. The mixture was extracted with isopropyl acetate (200 mL x 4) and concentrated in vacuo. The residue was mixed with silica gel (3 g) and crushed into a fine powder and dry loaded onto a Biotage 40 M cartridge. The residue was purified via gradient elution using 5% MeOH: (5% NEt3:CH2Cl2) to 15% MeOH:(5% NEt3:CH2Cl2) to give the triethylamine salt of 1 (0.281 g). The salt was treated with 1 M HCl and extracted with isopropyl acetate and the isopropyl acetate layer dried over MgSO4 and concentrated in vacuo to give 1 as a brown/green foam. Synthesis of 1 was reported previously by E. Tietze and O. Bayer 1939 Ann 540:189-210. TLC (MeOH: CH2Cl2:NEt3, 2:7:1) Rf = 0.23. 1H NMR (500 MHz, CD3OD) 6 7.94 (t, J = 7.6 Hz, IH), 7.97 (d, J= 9.4 Hz, IH), 8.02 (d, J= 9.2 Hz, IH), 8.11 (t, J= 7.7 Hz, 2H), 8.25 (s, IH), 8.39 (d, J= 9.1 Hz, IH), 8.98 (d, J= 9.3 Hz, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Sodium hydroxide (0.80 g, 20 mmol) was added to a stirring solution of pyranine (9.59 g, 18 mmol) dissolved in water (10 mL). The solution was stirred for 15 min and then concentrated under vacuum to dryness. A heated water bath was used to assist the distillation process. Acetic anhydride (100 mL) was added. The suspension was heated to reflux and stirred for 14 h. A white powder was collected via filtration and washed with dichloromethane and acetone; the powder was dried under vacuum (10.7 g, 18 mmol, quantitative yield).1H NMR (500 MHz, D2O) delta 9.24 (s, 1H), 9.23 (d, J = 10.0, 2H), 9.17 (d, J = 10.0, 1H), 9.13 (d, J = 9.5, 1H), 8.56 (s,1H), 8.51 (d, J = 9.5, 1H), and 2.65 (s, 3H); 13C NMR (500 MHz, D2O) delta 173.4, 144.5, 138.3, 136.2, 136.1, 129.7, 129.0, 127.1, 126.4, 125.6, 125.5, 125.3, 125.0, 125.0, 124.7, 123.4, 120.2, and 20.5; FTIR (KBr pellet) nu 3,470 (st) cm-1, 2,959 cm-1, 1,736 (m) cm-1, 1,569 (m) cm-1, 1,206 (st) cm-1, and 1,060 (st) cm-1. | |
92% | With sodium acetate; for 35h;Reflux; | Example 1 Trisodium 8-acetoxypyrene-1,3,6-trisulfonic acid (1) Trisodium 8-hydroxypyrene-1,3,6-trisulfonic acid (4.56 g, 8.70 mmol) and sodium acetate (71.4 mg, 0.88 mmol) were suspended in acetic anhydride (50 ml) and refluxed for 35 hours (Finider, B. et al. Photochemical & Photobiological Sciences 13, 548-562 (2014)). After the suspension was cooled down to room temperature, it was diluted with THF and filtered off. The residue was washed with acetone and dried under vacuum yielding a grey powder (5.52 g, 8.0 mmol, 92%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
245 g | With sodium hydroxide; In water; for 5h; | In 2000 ml three-necked flask into 1200 grams of concentrated sulfuric acid, stirring into the 120 grams of flowers, a little warming to promoteAfter all the dissolved, slowly warming to 90 C for 1 hour, three bottles with a water bath to cool below 40 C, drop the liquid sulfur black 480 grams, 3 hours drop finished. And then to maintain the temperature of about 100 C reaction for 5 hours, down to room temperature, the three bottles of material into the 720 grams of ice water, into a sticky material, filter dry filter cake, get pyrene tetrasulfonic acid tetrasodium salt. And then the pyrene tetrasulfonic acid tetrasodium salt dissolved in 1000 ml of water into the 2000 ml three-necked flask, stirring with a plate of sodium hydroxide to neutral, then add 300 grams of flaky sodium hydroxide, slowly warming To micro-boiling state for 5 hours. After cooling, the first with hydrochloric acid and PH value of 7 or so, then add 100 grams of sodium chloride stirring dissolved, slowly precipitated light yellow solid, filtered and dried to get 8-hydroxy-1,3, 6-pyrene three Sodium sulfonate salt about 245 grams. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N,N-dimethyl-formamide; trichlorophosphate; for 12h;Reflux; | 1) HPTS and phosphorus oxychloride are put into the reaction in a ratio of 1:3 equivalent, catalyzed by DMF, and heated to reflux for 12 hours; 2) The reaction product in the step 1) is slowly introduced into ice water and stirred, and the solid is precipitated, and suction-filtered to obtain HPTS-SO2Cl. The yield was 90%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.8% | With potassium hydroxide; In tetrahydrofuran; at 100℃; for 24h; | 5 mmol of trisodium 8-hydroxy-1,3,6-indoletrisulfonate, 30 mmol of allyl glycidyl ether, 75 mmol of KOH and 70 ml of THF are placed Mechanically agitated, reflux condenser and thermometer in a 250 ml four-neck glass flask. The reaction was stirred at 100 C for 24 h, and the pH of the reaction solution was maintained at about 14.0.The progress of the reaction was monitored by TLC to give an orange-red solution of product. After completion of the reaction, the solvent was evaporated to dryness crystals crystalsThe reaction product was obtained in a yield of 90.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 28% | With cobalt(II) chloride hexahydrate; nitric acid; In water; at 80℃; for 3h;Sealed tube; | Dissolve 5mmol of H4LCl2, 2mmol of HPTS and 3mmol of CoCl2 · 6H2O in 2ML of methanol, 2ML of nitric acid, and 3 drops of HNO3.After sealing the reaction placed in an oven at 80C for 3h. After taking it out, it was repeatedly washed with methanol, and the light microscope showed red massive crystals, that is, the prepared organic eutectic HPNPS-1, and the yield was about 28%. |
Tags: 6358-69-6 synthesis path| 6358-69-6 SDS| 6358-69-6 COA| 6358-69-6 purity| 6358-69-6 application| 6358-69-6 NMR| 6358-69-6 COA| 6358-69-6 structure
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