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CAS No. : | 521-31-3 | MDL No. : | MFCD00006890 |
Formula : | C8H7N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HWYHZTIRURJOHG-UHFFFAOYSA-N |
M.W : | 177.16 | Pubchem ID : | 10638 |
Synonyms : |
Diogenes reagent;3-Aminophthalhydrazide;NSC 5064
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 49.59 |
TPSA : | 91.74 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.16 cm/s |
Log Po/w (iLOGP) : | 0.78 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | -0.19 |
Log Po/w (MLOGP) : | 0.85 |
Log Po/w (SILICOS-IT) : | 1.48 |
Consensus Log Po/w : | 0.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.7 |
Solubility : | 3.51 mg/ml ; 0.0198 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.8 |
Solubility : | 2.81 mg/ml ; 0.0159 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.78 |
Solubility : | 0.293 mg/ml ; 0.00166 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
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 |
---|---|---|
83% | at 35℃; for 5 h; | To a three-necked flask was added 5 gl0 wtpercent palladium content meter) palladium on carbon, Stir evenly after heating to 35 ° C, A solution of 260 g of 85 wtpercent aqueous solution of formic acid was slowly added dropwise with stirring, The dropping time was 2 hours, and after the dropwise addition, Continue to react for 3 hours, the point plate to confirm 3-nitro phthalic acid hydrazide has been completely consumed, The pH was adjusted to 3-4 with 35 wtpercent concentrated hydrochloric acid and heated to 100 ° C, Hot filter, the filtrate cooled to l ° C, a large number of precipitation, Precipitate out completely after filtration, the filtrate for organic solvent recovery, The filter cake was washed with 300 ml of deionized water and dried to give 182 g of luminol (3-aminophthalohydrazide). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide;immobilized horseradish peroxidase; In water;pH 8.5;Porous hydrogel used;Product distribution / selectivity; | Whereas porous HRP-laden hydrogel emits intense blue light (FIG. 17A), non-porous versions show essentially no light emission (FIG. 17B). Porous hydrogel soaked in a solution of free HRP followed by immersion in a luminol solution shows blue light emission in the whole solution (FIG. 17C) supporting that HRP is covalently immobilized on the hydrogel in the cases for FIG. 17A.FIGS. 17A-17C depict biocatalysis of luminol reaction by HRP covalently immobilized on porous polyacrylic amide hydrogel (A), non-porous hydrogel (B), and by HRP non-covalently absorbed in a porous hydrogel (C). Schematic representations of hydrogels are shown above each figure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triethylamine; In N-methyl-acetamide; | EXAMPLE 2 An alternate procedure for the preparation of N-(chloroacetyl)-3-aminophthalhydrazide is as follows. 3-Aminophthalhydrazide (Aldrich), 5.0 g (0.0282 mol), was dissolved in 50 mL of dimethylformamide in a 100 mL round bottom flask containing a magnetic stirring bar. Triethylamine, 2.85 g, was added to the flask, and then chloroacetyl chloride (Aldrich), 3.34 g (0.0296), was added dropwise over 15 minutes. After the addition of the acid chloride was complete, the mixture was stirred for 30 minutes at room temperature. Triethylamine hydrochloride is formed during this time and precipitates from solution. After thirty minutes, the reaction mixture was poured into cold water, and the precipitate which formed was collected by filtration. After washing sequentially with 50 mL portions of cold water and then ethyl ether, and drying, 5.6 g (78 % yield) of a yellow powder was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; | EXAMPLE 14 Synthesis of 3-formylamino-phthalhydrazide (Compound 22) Process 1. 1.0 gm of 3-aminophthalhydrazide and 70.0 ml of 98% formic acid was refluxed for 60 minutes. The solution was cooled to room temperature and then to ice temperature. The precipitate was filtered off at 4 C., and washed with cold water. It was then dried under vacuum, giving 1.15 gm (99.0%) of a bright yellow product which was crystallized from dimethylsulphoxide. Melting point 293 C. to 294 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In acetic acid; | EXAMPLE 2 In 100 ml of glacial acetic acid containing 5 ml of pyridine were suspended 5.3 g of 5-amino-2,3-dihydro-1,4-phthalazinedione and 3.1 g of glutaric anhydride and the suspension was heated under reflux while stirring. About 30 minutes after the starting of the reflux, the suspended materials were dissolved to form a solution and after about 30 additional minutes the reaction product started to precipitate from the solution. The reaction mixture was cooled about 30 minutes after the reaction was started to obtain crude brown product. The crude product was treated in a way similar to that of Example 1 to obtain 4.2 g of 5-glutaramido-2,3-dihydro-1,4-phthalazinedione as white powdery crystals which were molten at a temperature between 295 - 297 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; gold; 1-(2,3,4-trimethoxybenzyl)piperazine hydrochloride; In water;Alkaline conditions; | As shown in Fig. 1, flow lines were connected with luminol solution, AuNPs solution, N-bromosuccinimide solution and trimetazidine solution, respectively. Peristaltic pumps were started to drive the solutions into the flow system. After a stable baseline was recorded, luminol solution (90muL) was injected into AuNPs solution by an injection valve, which was then combined with the merged stream of trimetazidine solution and N-bromosuccinimide solution. The CL signal produced in the flow cell was detected with a CR105 photomultiplier tube (Hamamatsu Photonics (China) Co., Ltd.). The concentration of trimetazidine was quantified by the enhanced CL intensity DeltaI (DeltaI=Is-Ib), where Is and Ib were the CL signals in the presence of trimetazidine and blank, respectively. | |
With [Cu2(N,N'-dibenzylethylenediamine)2(tetraacetylethane)](ClO4)2; dihydrogen peroxide; In methanol; aq. phosphate buffer; water;pH 7.5; | Briefly, glass cells were filled with 300 lL of luminol (variouspH in 0.1 M phosphate buffer) at particular concentrations, 50 lLof [Cu2L2(TAE)]X2 (Various concentrations in methanol), 50 lL ofdeionized-distilled water or R-SH (GSH or CySH, Various concentrationsin water) and 50 lL of H2O2 (various concentrations inwater) as a complementary reagent was injected to initiate thelight emission. The CL signal kinetics (intensity versus times) wererecorded soon after mixing of the solutions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With formic acid; palladium 10% on activated carbon; hydrogen; at 35℃; for 5h; | To a three-necked flask was added 5 gl0 wt% palladium content meter) palladium on carbon, Stir evenly after heating to 35 C, A solution of 260 g of 85 wt% aqueous solution of formic acid was slowly added dropwise with stirring, The dropping time was 2 hours, and after the dropwise addition, Continue to react for 3 hours, the point plate to confirm 3-nitro phthalic acid hydrazide has been completely consumed, The pH was adjusted to 3-4 with 35 wt% concentrated hydrochloric acid and heated to 100 C, Hot filter, the filtrate cooled to l C, a large number of precipitation, Precipitate out completely after filtration, the filtrate for organic solvent recovery, The filter cake was washed with 300 ml of deionized water and dried to give 182 g of luminol (3-aminophthalohydrazide). |
2nd Step:3-nitrophthalhydrazide-5-amino-2,3-dihy-drophthalazine-1,4-dioneBatch Sizes: Quantity Substance Equivalents Batch [mol] 3-Nitrophtalhydrazid 1 100 g 0.48 Sodium dithionite 3.6 300 g 1.73 NaOH (3M) 17 (vol/m) 1,700 mL N/A Acetic acid 7.2 200 mL (210 g) 3.5 Water for washing 3 × 1.5 (vol/m) 510 mL N/A (3 × 170 mL) In a second step, 3-nitrophthalhydrazide was reacted to 5-amino-2,3-dihydrophthalazin-1,4-dione by that 3-nitrophthalhydrazide (100 g, 0.48 mol) 48.3 mmol) is dissolved in 3 molar sodium hydroxide solution (1,700 mL) while heating to approx. 50-60 C. To this solution the sodium dithionite (300 g, 1.73 mol) is added in portions. Thereby, the temperature of the reaction mixture will rise to approx. 80 C. After complete addition of sodium dithionite, the reaction mixture is heated for approx. 4 h for reflux. Acetic acid (200 mL, 1.73 mol) is added, and the reaction mixture is cooled down over night. The resulting precipitate is isolated and washed with water (3×170 mL). The product is dried at the rotary evaporator at approx. 80 C./20+/-10 mbar. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium dithionite; | The starting point of the synthesis for all production examples is luminol known from prior art, which can for instance be produced according to the following reaction scheme: Here is shown the synthesis of luminol (iii) by reaction of 3-nitrophthalic acid (i) that can be reduced in alkaline medium by hydrazine or one of its salts, or other suitable reduction agents, for instance ammonium sulfite or triethylene glycol, to luminol via 3-nitrophthalic anhydride (ii). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | <strong>[521-31-3]Luminol</strong> wasdiazotized as reported.8;16 The azo compound was synthesized by the coupling of diazotized luminol with theunsaturated 1,3-diketone.To a stirred suspension of luminol (0.885 g, 0.005 mol) in 6 N HCl (3 mL) kept cold below 5 C in anice-salt bath, an aqueous solution of NaNO2 (0.0345 g in 1 mL of distilled water) was added dropwise. Thecold mixture was stirred further for 1 h and then ltered quickly. The ltrate, after destroying excess nitrousacid with urea, was added slowly to a stirred suspension of unsaturated diketone (1.38 g, 0.005 mol) dissolvedin methanol (10 mL) at 0 C. Sodium acetate was added to maintain the pH of the medium at around 6. Theprecipitated azo dye was ltered, washed with water, and recrystallized from hot benzene. |
Tags: 521-31-3 synthesis path| 521-31-3 SDS| 521-31-3 COA| 521-31-3 purity| 521-31-3 application| 521-31-3 NMR| 521-31-3 COA| 521-31-3 structure
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