Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 611-64-3 | MDL No. : | MFCD00143523 |
Formula : | C14H11N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FLDRLXJNISEWNZ-UHFFFAOYSA-N |
M.W : | 193.24 | Pubchem ID : | 11913 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 14 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.22 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.72 cm/s |
Log Po/w (iLOGP) : | 2.45 |
Log Po/w (XLOGP3) : | 3.89 |
Log Po/w (WLOGP) : | 3.7 |
Log Po/w (MLOGP) : | 3.33 |
Log Po/w (SILICOS-IT) : | 4.0 |
Consensus Log Po/w : | 3.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.18 |
Solubility : | 0.0128 mg/ml ; 0.0000661 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.86 |
Solubility : | 0.0268 mg/ml ; 0.000139 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.77 |
Solubility : | 0.000331 mg/ml ; 0.00000171 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.05 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
66% | With zinc(II) chloride at 130℃; for 3h; | General procedure for the synthesis of 9-[(E)-2-(nitrophenyl)ethenyl]acridine 6a, b General procedure: A mixture of 9-methylacridine (5) (1.0 g, 5.17 mmol),appropriate aldehyde (0.782 g, 5.17 mmol), and zincchloride (0.776 g, 5.70 mmol) was heated at 130 °C for 3 h.The reaction mixture was cooled to room temperature andwas partitioned between aqueous sodium hydroxide andchloroform. The organic phase was washed with water andbrine, dried over magnesium sulfate, filtered, and concentratedin vacuo. The residue was purified by silica gelcolumn chromatography (4:1 hexane-acetone) to producecompound 6 (Tsukamoto et al. 2009). 9-[(E)-2-(4-nitrophenyl)ethenyl]acridine (6a) Yield 1.12mg, 66%. Bright yellow solid. Mp 286-287 °C. [Found: C77.17; H 4.25; N 8.34; C21H14N2O2 (326.354) requires C77.29; H 4.32; N 8.58%]; 1H (600 MHz, DMSO-d6): 8.49(1H, d, J 16.2, H-2), 8.41 (2H, d, J 9.0, H-1′,8′), 8.34 (2H,d, J 8.7, H-3″,5″), 8.20 (2H, d, J 8.5, H-4′,5′), 8.16 (2H, d, J8.7, H-2″,6″), 7.89 (2H, ddd, J 8.8, 6.5, 1.4, H-3′,6′), 7.66(2H, ddd, J 8.9, 6.5, 1.3, H-2′,7′), 7.32 (1H, d, J 16.6, H-1);13C (150MHz, DMSO-d6): 148.2 (C-4′a,10′a), 147.0 (C-4″), 142.9 (C-1″), 141.9 (C-9′), 137.3 (C-1), 130.3 (C-3′,6′),129.6 (C-4′,5′), 128.3 (C-2″,6″), 127.2 (C-2), 126.2 (C-2′,7′), 125.9 (C-1′,8′), 124.0 (C-3″,5″), 123.6 (C-8′a,9′a);15N (61 MHz, DMSO-d6): -74.4 (N-10′), -9.8 (NO2) ppm. |
31% | With acetic anhydride In acetic acid for 5h; Heating; | |
With zinc(II) chloride |
With zinc(II) chloride at 130℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With acetic anhydride In acetic acid for 5h; Heating; | |
With zinc(II) chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With acetic anhydride In acetic acid for 5h; Heating; | |
With zinc(II) chloride at 140 - 145℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With acetic anhydride In acetic acid for 5h; Heating; | |
at 135℃; | ||
With zinc(II) chloride |
With acetic anhydride | ||
In acetic anhydride Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In toluene for 2h; Reflux; | |
71% | In toluene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | In acetonitrile for 12h; Reflux; | |
51% | In acetonitrile for 6h; Reflux; | 1.B.2; 2.A.2 (2) Synthesis of 9,10-dimethylacridine iodide salt: 9-Methylacridine (1.0 g, 5 mmol) was dissolved in 10 mL of acetonitrile,Add methyl iodide (1.4g, 10mmol) refluxed 6h (methyl iodide volatile,The reaction process may be appropriate to add methyl iodide);After the reaction was cooled liquid,The precipitated solid was filtered,And acetonitrile:Methanol = 4: 1 mixed solvent was recrystallized,Finally, yellow flaky crystals were obtained (yield 51%). |
48% | In tetrahydrofuran; acetonitrile at 40℃; for 25h; |
at 100℃; | ||
In tetrahydrofuran; acetonitrile at 40℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dichloro-acetic acid; [bis(acetoxy)iodo]benzene; water In dimethyl sulfoxide at 20℃; for 48h; Sealed tube; chemoselective reaction; | |
81% | With copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 130℃; for 4h; Sealed tube; | |
77% | With selenium(IV) oxide In 1,4-dioxane at 110℃; for 1.5h; Inert atmosphere; |
68% | With selenium(IV) oxide In 1,4-dioxane for 2.5h; Reflux; | |
62% | With magnesium sulfate; pyridinium chlorochromate In dichloromethane Ambient temperature; | |
55% | With magnesium sulfate; pyridinium chlorochromate In dichloromethane at 20℃; for 18h; | |
50% | With selenium(IV) oxide In 1,4-dioxane; water for 2h; Heating; | |
With selenium(IV) oxide; acetic acid | ||
With magnesium sulfate; pyridinium chlorochromate In dichloromethane at 20℃; for 48h; | 1 Example 1 - Preparation procedure of acridin-9-carboxyaldehvde:Diphenylamine, acetic acid and zinc chloride are heated at a temperature of 220 0C, for 8 hours. The reaction mixture was treated, initially, with 10% sulfuric acid followed by alkalinization with 30% ammonia solution. The 9- methyl-acridine was isolated though benzene extraction and purified trough flash chromatography in silica gel 60.In the 9-methyl-acridine oxidation, piridinium chlorochromate (PCC) and magnesium sulfate are put in a flask, in presence of dichloromethane, with stirring, followed by addition of 9-methyl-acridine. The agitation was kept at room temperature, under inert atmosphere, for 48 hours. The acridine-9- carboxyaldehyde compound was extracted from the medium with ethylic ether and evaporated to dryness. The aldehyde obtained was purified trough flash chromatography in silica gel 60. | |
With pyridinium chlorochromate | ||
With pyridinium chlorochromate | ||
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 6 h 2: sodium; 2-nitropropane / methanol; dimethyl sulfoxide / 20 °C | ||
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 6 h / 80 °C 2: sodium; 2-nitropropane / dimethyl sulfoxide / 2 h / 20 °C | ||
With pyridinium chlorochromate In dichloromethane at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With N-Bromosuccinimide; dibenzoyl peroxide In chloroform for 5h; Heating; | |
95% | With N-Bromosuccinimide; dibenzoyl peroxide In 1,1,2,2-tetrachloroethylene at 20 - 60℃; for 5h; Large scale; Further stages; | 1-6 Example 6 The preparation method of 9-bromomethyl acridine After mixing (60kg) 9-methylacridine and (300kg) tetrachloroethylene at room temperature, add (38kg) N bromosuccinimide and (3kg) BPO under stirring, and stir for 60min For dispersion, the temperature is raised to 40°C, and the reaction is kept for 1 hour. (2) Then the temperature was increased to 55C and the reaction was incubated for 1h.(3) After that, the temperature was lowered to 25° C., N-bromosuccinimide was added (18.8 kg), and the temperature was raised to 60° C. and the reaction was incubated, TLCCentral control, the reaction is complete in 2h.[0060] (4) Cool down to 25° C. and keep the temperature for 1 h. The solid obtained by filtration is the crude 9-bromomethyl acridine, which is then added to the crude product.Add (240kg) 50% methanol aqueous solution, heat up to 20°C, after keeping it for 3h, decrease the temperature to 25°C, keep it warm and stir for 2h, filter and dryObtained a yellow solid powder of 9-bromomethylacridine (81.2kg, purity 98.9%, yield 95.0%) |
87% | Stage #1: 9-methyl-acridine With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 60℃; for 0.5h; Stage #2: With N-Bromosuccinimide In tetrachloromethane at 60 - 80℃; for 4h; | 5.2.10 9-(Bromomethyl)acridine (12) To a solution of 11 (2.0g, 10.4mmol) in CCl4 (100mL) was added AIBN (0.17g, 1.0mmol) and heated to 60°C under stirring for 30min. Then NBS (0.17g, 11.4mmol) was added and the reaction mixture was heated under refluxing conditions for 4h. After completion of the reaction, the reaction solution was diluted with CH2Cl2. The organic layer was separated, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by silica gel using petroleum ether/EtOAc (5/1) as eluent to afford intermediate 12 (2.45g) in 87% yield. 1H NMR (400MHz, DMSO-d6) δ 8.85 (d, J=8.8Hz, 1H), 8.29 (d, J=8.6Hz, 4H), 7.98-7.94 (m, 2H), 7.80 (d, J=7.7Hz, 1H), 5.89 (s, 2H). MS (ESI) m/z calcd for C14H10BrN [M+ H]+, 272.0, found: 274.3. |
87% | Stage #1: 9-methyl-acridine With 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 60℃; for 0.5h; Stage #2: With N-Bromosuccinimide In tetrachloromethane for 4h; Reflux; | 7 Example 7: Preparation of 9-(bromomethyl)acridine (9) The intermediate 9-methylacridine (2.0 g, 10.4 mmol) prepared in Example 6 was weighed, 100 mL of carbon tetrachloride was added as a solvent, and the temperature was raised to 60°C. Then, azobisisobutyronitrile (0.17 g, 1.0 mmol) was added as an initiator to the solution, and the mixture was stirred at this temperature for 30 min. Then N-bromosuccinimide (0.17g, 11.4mmol) was added, and the temperature was raised to a reflux state, and heating was continued for 4h. After the completion of the reaction was monitored by TLC, dichloromethane was added to dilute. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. Then, it was separated by silica gel column chromatography (petroleum ether/ethyl acetate=5:1) to obtain 2.45 g of intermediate 9 with a yield of 87%. |
80% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 6h; Irradiation; | |
77% | With N-Bromosuccinimide In dichloromethane | 9-(bromomethyl)acridine (10) 9-(bromomethyl)acridine (10) To a solution of 9-methylacridine (1.93 g, 10 mmol) in dichloromethane (100 mL) was added NBS (1.78 g, 10 mmol) portion-wise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1:5) as eluent to afford 10 (2.08 g) in 77% yield. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.8 Hz, 4H), 7.81 (t, J=8.0 Hz, 2H), 7.68 (t, J=8.0 Hz, 2H), 5.42 (s, 2H). 13C NMR (400 MHz, CDCl3) δ 148.9, 138.7, 130.5, 130.1, 126.8, 123.8, 123.4, 23.1. MS (FAB) m/z Calcd for C14H10BrN 272.1. Found 2722. [M]+. |
77% | With N-Bromosuccinimide In dichloromethane at 20℃; Cooling with ice; | [0115] To a solution of 9-methylacridine (1.93 g, 10 mmol) in dichloromethane (100 mE) was added N135 (1.78 g, 10 mmol) portion-wise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by silica gel chromatography using ethyl acetate and petroleum ether (EA:PE=1 :5) as eluent to afford 10(2.08 g) in 77% yield. 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=8.8 Hz, 4H), 7.81 (t, J=8.0 Hz, 2H), 7.68 (t, J=8.0 Hz, 2H), 5.42 (s, 2H). 13C NMR (400 MHz, CDCl3)δ148.9,138.7, 130.5, 130.1,126.8,123.8,123.4,23.1. MS (FAI3)mlz Calcd for C,4H,0BrN 272.1. Found 2722. [M]+. |
77% | With N-Bromosuccinimide In dichloromethane at 20℃; Cooling with ice; | 9-Bromomethylacridine (2) To a solution of 9-methylacridine (0.193 g, 1 mmol) in dichloromethane (10 mL) was added N-bromosuccinimide (0.178 g, 1 mmol) portionwise in an ice-water bath. After complete addition, the solution mixture was warmed to room temperature and stirred overnight. The resulting solution was washed with water and brine. The organic phase was dried over anhydrous sodium sulphate, and the solvent was removed. The residue was purified by column chromatography (eluent ethyl acetate/petroleum ether = 1/5 v/v). Yield 77%; the % of elementsfound/calculated, C 61.26/61.79, H 3.64/3.70, N 5.03/5.15; 1H NMR (CDCl3), δ, ppm (J, Hz): 5.38 (2H, s); 7.62 (2H, t, J = 7.7); 7.78 (2H, t, J = 7.7); 8.31 (4H, d, J = 8.8). |
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide | ||
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane Reflux; | ||
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux; | ||
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 6h; | ||
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; potassium hexacyanoferrate(III); benzene | ||
With air for 336h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper; sodium carbonate; nitrobenzene at 220℃; und Erwaermen des Reaktionsprodukts mit Eisessig und wenig konz.Schwefelsaeure auf dem Wasserbad.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; zinc(II) chloride at 220℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methyl magnesium iodide; dibutyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With 2,2-dimethoxy-propane; zinc(II) chloride In neat (no solvent) at 100℃; for 0.133333h; Microwave irradiation; Green chemistry; | |
81% | With zinc(II) chloride at 220℃; for 17h; | 9-Methylacridine (1). A mixture of 10 g of diphenylamine(59.1 mmol), acetic acid (10.0 ml), and anhydrous zinc chloride(40.0 g, 293.5 mmol) was heated at 220 C for 17 h. The reactionmixturewas digested with hot 10% aqueous sulphuric acid and thenstrongly alkalified with concentrated aqueous ammonia to dissolvethe zinc chloride. The insoluble residuewas extracted with toluene.The organic phase was washed with water (100 mL) and dried oversodium sulphate. After evaporation of the solvent, the crudeproductwas purified by column chromatography (eluent n-hexane/ethyl acetate 5/1 v/v). Yield 81%; m.p. 391 K; the % of elementsfound/calculated, C 86.93/87.01, H 5.74/5.74, N 7.09/7.25; 1H NMR(CD3CN), d, ppm (J, Hz): 3.06 (3H, s); 7.52 (2H, t, J 7.5); 7.71 (2H, t,J 7.4); 8.04 (2H, d, J 8.6); 8.28 (2H, d, J 8.8). |
81% | With zinc(II) chloride at 220℃; for 17h; | 9-Methylacridine (1) A mixture of 10 g of diphenylamine (59.1 mmol), acetic acid (10.0 mL) and anhydrous zinc chloride (40.0 g, 293.5 mmol) was heated at 220 °C for 17 h. The reaction mixture was digested with hot 10% aqueous sulphuric acid and then strongly alkalified with concentrated aqueous ammonia to dissolve the zinc chloride. The insoluble residue was extracted with toluene.The organic phase was washed with water (100 mL) and dried over sodium sulphate. After evaporation of the solvent, the crude product was purified by column chromatography (eluent n-hexane/ethyl acetate = 5/1 v/v). Yield 81%; the % of elements found/calculated, C 86.93/87.01, H 5.74/5.74, N 7.09/7.25; 1H NMR (CD3CN), δ, ppm (J, Hz): 3.06 (3H, s); 7.52 (2H, t, J = 7.5); 7.71 (2H, t,J = 7.4); 8.04 (2H, d, J = 8.6); 8.28 (2H, d, J = 8.8). |
81% | With zinc(II) chloride at 180 - 200℃; | 5.2.9 9-Methylacridine (11) A mixture of N,N-diphenylamine (3.0g, 17.7mmol), AcOH (3.2g, 53.2mmol), and ZnCl2 (12.0g, 88.6mmol) was heated with efficient stirring. When the temperature reached to 180°C, the excess AcOH was removed from the reaction mixture by distillation. Then, the reaction mixture was heated at 220°C for additional 5h under stirring. After the addition of aqueous ammonia solution, the yellow precipitates were obtained by filtration and subsequently dissolved in CH2Cl2. The CH2Cl2 solution was neutralized by washing with aqueous NaHCO3 and brine, dried over Na2SO4, filtrated, concentrated under reduced pressure. The residue was purified on silica gel with petroleum ether/EtOAc (5/1), yielding the pale yellow solid (2.77g, 81%). 1H NMR (400MHz, Chloroform-d) δ 8.24 (dd, J=12.0, 8.9Hz, 4H), 7.79-7.75 (m, 2H), 7.58-7.54 (m, 2H), 3.13 (s, 3H). MS (ESI) m/z calcd for C14H11N [M+ H]+, 194.1, found: 194.4. |
81% | With zinc(II) chloride at 180 - 220℃; for 5h; | 6 Example 6: Preparation of 9-methylacridine (8) Weigh the raw materials N,N-diphenylamine (3.0 g, 17.7 mmol) and zinc chloride (12.0 g, 88.6 mmol), and add glacial acetic acid (3.2 g, 53.2 mmol) to them. When the temperature was raised to 180°C, the excess glacial acetic acid was removed from the reaction mixture by distillation, and then the temperature was continued to rise, and heating was continued at 220°C for 5 hours. After the completion of the reaction was monitored by TLC, the reaction solution was cooled to room temperature, and then an aqueous ammonia solution was added, and a yellow precipitate was obtained by filtration. The solid was then dissolved in dichloromethane, washed with aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. Then, it was separated by silica gel column chromatography (petroleum ether/ethyl acetate=5:1) to obtain 2.77 g of light yellow solid, namely Intermediate 8, with a yield of 81%. |
79% | With zinc(II) chloride at 200 - 210℃; for 0.0833333h; microwave irradiation; | |
73% | With zinc(II) chloride at 220℃; for 6h; | |
73% | With zinc(II) chloride at 180 - 220℃; for 7.5h; | |
72% | With zinc(II) chloride at 150 - 215℃; for 5h; | |
71% | With zinc(II) chloride at 150 - 215℃; for 5h; | 1.B.1; 2.A.1 (1) Synthesis of 9-methylacridine: The reaction was carried out using the Berthsen, A.Y acridine synthesis method: N, N-diphenylamine (5.0 g,30 mmol), acetic acid (5.0 g, 84 mmol) and zinc chloride (21.3 g, 156 mmol) were added and the mixture was heated to 150 ° C.Until the solid is fully dissolved, the process of solid from white to yellow and finally all of the black change; and then heated to 215° C, excess acetic acid is volatilized from the reaction mixture for 5 hours; after the reaction is cooled, the black solidThe product was reheated and melted, poured into a beaker containing 200 mL of ice water, and the pH of the whole system was adjusted to 13 to 14 with ammonia,After the bottom solid was completely solubilized with ethyl acetate, the whole system was filtered and the filtrate was separated into an aqueous phase and an organic phase. The aqueous phase was extracted with ethyl acetateExtracted three times, the resulting ethyl acetate solution was mixed with the organic phase, washed three times, and finally the organic phase was combined, dried over anhydrous MgSO4Dried and dried to give the crude product; the crude product was separated by silica gel column chromatography (eluent: dichloromethane / ethyl acetate = 5/1)The final soil was obtained (yield 71%). |
67% | at 220℃; for 6h; | |
59% | With zinc(II) chloride at 220℃; for 14h; | |
49% | With zinc(II) chloride at 210 - 220℃; for 10h; | |
40% | With zinc(II) chloride at 220℃; for 6h; | |
26.5% | With zinc(II) chloride at 170℃; for 17h; | |
22% | With PPA at 170 - 205℃; for 2.5h; | |
18% | With zinc(II) chloride at 240℃; for 16.5h; Inert atmosphere; | |
With zinc(II) chloride | ||
With zinc(II) chloride at 215℃; for 5h; | ||
With zinc(II) chloride at 220℃; for 8h; | 1 Example 1 - Preparation procedure of acridin-9-carboxyaldehvde:Diphenylamine, acetic acid and zinc chloride are heated at a temperature of 220 0C, for 8 hours. The reaction mixture was treated, initially, with 10% sulfuric acid followed by alkalinization with 30% ammonia solution. The 9- methyl-acridine was isolated though benzene extraction and purified trough flash chromatography in silica gel 60.In the 9-methyl-acridine oxidation, piridinium chlorochromate (PCC) and magnesium sulfate are put in a flask, in presence of dichloromethane, with stirring, followed by addition of 9-methyl-acridine. The agitation was kept at room temperature, under inert atmosphere, for 48 hours. The acridine-9- carboxyaldehyde compound was extracted from the medium with ethylic ether and evaporated to dryness. The aldehyde obtained was purified trough flash chromatography in silica gel 60. | |
With zinc(II) chloride at 190℃; | ||
With zinc(II) chloride | ||
With zinc(II) chloride at 180 - 220℃; for 5h; | ||
With zinc(II) chloride | ||
With zinc(II) chloride at 230℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With acetic anhydride for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With acetic anhydride for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With acetic acid; triethylamine In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid; triethylamine In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With acetic acid; triethylamine In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; triethylamine In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 1% 2: 80% | With hydrogenchloride; aluminum nickel In 1,4-dioxane at 95℃; for 3h; sonication; | |
1: 91.3 %Chromat. 2: 8.7 %Chromat. | With RuH2(H2)2(tricyclohexylphosphine)2; hydrogen In cyclohexane at 80℃; for 24h; | |
1: 70.8 %Chromat. 2: 29.2 %Chromat. | With [RuH2(η4-9-methylacridine){P(C6H11)3}2]; hydrogen In cyclohexane at 80℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium acetate In ethanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With acetic anhydride In acetic acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With acetic anhydride In acetic acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With acetic anhydride In acetic acid for 5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 92% 2: 8% | With iodine; hypophosphorous acid In acetic acid for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic anhydride at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 35.5% 2: 6.6% | Stage #1: 9-methyl-acridine With sodium acetate In acetic acid at 80℃; Stage #2: 5-bromo-2-thiophencarboxaldehyde In acetic acid for 8h; Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In tetrahydrofuran; water | Preparation of 9-(4-nitrostyryl)acridine by Melting Preparation of 9-(4-nitrostyryl)acridine by Melting A mixture of 9-methylacridine (4.83 g, 25.0 mmol), 4-nitrobenzaldehyde (4.23 g, 31.25 mmol) and zinc chloride (5.06 g, 31.25 mmol) is heated at 130° C. for 3 hours with an oil bath. The solid recovered is heated in a solution of sodium metabisulfite in order to eliminate the excess aldehyde and the hot mixture is filtered. Precipitates obtained are dissolved in a minimum amount of tetrahydrofuran and water is added to the solution so as to obtain the product in the form of precipitates. These precipitates are recovered by filtration and dried. The product can be recrystallized from ethanol. The yield is 35%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 99 percent / N-bromosuccinimide; benzoyl peroxide / CHCl3 / 5 h / Heating 2: 66 percent / K2CO3 / acetonitrile / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium acetate / acetic acid / 80 °C 1.2: 6.6 percent / acetic acid / 8 h / Heating 2.1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C 2.2: 97 percent / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 20 °C 3.1: 82.9 percent / aq. HCl / 0.5 h / 20 °C / pH 1 | ||
Multi-step reaction with 3 steps 1.1: sodium acetate / acetic acid / 80 °C 1.2: 35.5 percent / acetic acid / 8 h / Heating 2.1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C 2.2: 97 percent / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 20 °C 3.1: 82.9 percent / aq. HCl / 0.5 h / 20 °C / pH 1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium acetate / acetic acid / 80 °C 1.2: 6.6 percent / acetic acid / 8 h / Heating 2.1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C 2.2: 97 percent / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 20 °C | ||
Multi-step reaction with 2 steps 1.1: sodium acetate / acetic acid / 80 °C 1.2: 35.5 percent / acetic acid / 8 h / Heating 2.1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C 2.2: 97 percent / [Pd(PPh3)4] / 1,2-dimethoxy-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: acetic anhydride / 0 °C 2: 70 percent / 5 h / 140 °C 3: aq. KOH / tetrahydrofuran; methanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 55 percent / MgSO4; PCC / CH2Cl2 / 18 h / 20 °C 2: 49 percent / piperidine / benzene / 8 h / 110 °C | ||
Multi-step reaction with 2 steps 1: pyridinium chlorochromate 2: triethylamine / 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 55 percent / MgSO4; PCC / CH2Cl2 / 18 h / 20 °C 2: 49 percent / piperidine / benzene / 8 h / 110 °C 3: 96 percent / piperidine / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 55 percent / MgSO4; PCC / CH2Cl2 / 18 h / 20 °C 2: 49 percent / piperidine / benzene / 8 h / 110 °C 3: 22 percent Spectr. / piperidine / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 55 percent / MgSO4; PCC / CH2Cl2 / 18 h / 20 °C 2: 49 percent / piperidine / benzene / 8 h / 110 °C 3: 78 percent Spectr. / piperidine / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 55 percent / MgSO4; PCC / CH2Cl2 / 18 h / 20 °C 2: 49 percent / piperidine / benzene / 8 h / 110 °C 3: 60 percent / piperidine / ethanol / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaH / dimethylformamide / 0 °C 2: 2.) 2N HCl / 1.) THF, -70 deg C, 30 min, 2.) EtOH, 50 deg C, 5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dibenzoyl peroxide; tetrachloromethane; <i>N</i>-bromo-succinimide 2: ethanol 3: water; ethanol; NaOH-solution | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 6 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 6 h / 20 °C 3: acetonitrile; water / Photolysis |
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 6 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 6 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 6 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 7 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 7 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 8 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 8 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 8 h / 20 °C 3: acetonitrile; water / Photolysis | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 9 h / 20 °C 3: acetonitrile; water / Photolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dibenzoyl peroxide; tetrachloromethane; <i>N</i>-bromo-succinimide 2: ethanol | ||
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux 2: potassium carbonate / dichloromethane / 8 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dibutyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dibutyl ether 2: potassium carbonate; copper (I)-iodide; nitrobenzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dibutyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sulfuric acid at 0 - 50℃; for 15h; | 23 PREPARATION 23; Preparation of 4,5-bis(bromomethyl)-9-methylacridine; A solution of 9-methylacridine (2.16 g, 11.16 mmol) and bromo(methoxy)methane (6.08 g, 44.64 mmol) in concentrated sulfuric acid (25 ml.) was stirred under nitrogen at 50 0C for 14 h. The reaction mixture was poured on ice and stirred for 1 h. The solid obtained was collected by filtration, then dissolved in chloroform. The resulting solution was dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was recrystallized from dichloroethane/hexane to afford 4,5-bis(bromomethyl)-9-methylacridine as an off-white solid in 40% yield (1.7 g): MS (ES+) m/z 378.1 (M + 1 ), 380.3 (M + 1 ). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 950℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 2% | at 750℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | at 125℃; for 4h; | |
46% | at 125℃; for 4h; | 17 9-Methyl-10-(3-sulfopropyl)acridinium hydroxide inner salt. This compound was prepared using a method reported in Adamczyk, M.; Chen, Y. Y.; Mattingly, P. G.; Pan, Y.; Rege, S. J. Org. Chem. 1998, 63, 5636. A mixture of 9-methylacridine (270 mg, 1.4 mmol) and 1,3-propane sultone (1.8 g, 14.8 mmol) was stirred in a pressure vessel for 4 h at 125° C. After cooling down, the mixture was purified by column chromatography (SiO2, solvent gradient from 5:95 MeOH/CH2Cl2 to 15:85 MeOH/CH2Cl2) to obtain a mixture of yellow strongly fluorescent fractions. This mixture was concentrated and heated with 37 mL 1N HCl to reflux for 4.5 h. Upon cooling down overnight, the water was evaporated off and the oily residue was purified by column chromatography (SiO2, gradient from CH2Cl2 to 1:9 CH2Cl2/MeOH) to furnish 9-methyl-10-(3-sulfopropyl)acridinium hydroxide inner salt as a yellow solid (202 mg, 46%). 1H NMR (400 MHz, CD3OD): δ 2.60 (m, 2 H), 3.23 (t, J=6.2 Hz, 2 H), 3.56 (s, 3 H), 5.63 (t, J=8.8 Hz, 2 H), 8.01 (m, 2 H), 8.44 (m, 2 step function. This is in vast contrast to di-4-ANEQPTMA and di-4-ANHTQPTMA, where the exponential time constant exceeds 30 ms, making them unusable for electrophysiological applications. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 100℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With acetic acid; zinc(II) chloride at 120℃; for 15h; Darkness; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane 2: triethyl phosphite | ||
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / dichloromethane / 20 °C / Cooling with ice 2: 4 h / Reflux | ||
Multi-step reaction with 2 steps 1.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 1.2: 4 h / 60 - 80 °C 2.1: 4 h / Reflux |
Multi-step reaction with 2 steps 1.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 1.2: 4 h / Reflux 2.1: 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane 2: triethyl phosphite 3: NaH / tetrahydrofuran | ||
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / dichloromethane / 20 °C / Cooling with ice 2: 4 h / Reflux 3: sodium hydride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane 2: triethyl phosphite 3: NaH / tetrahydrofuran 4: acetonitrile | ||
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / dichloromethane / 20 °C / Cooling with ice 2: 4 h / Reflux 3: sodium hydride / tetrahydrofuran / 20 °C 4: acetonitrile / 24 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With tris-(dibenzylideneacetone)dipalladium(0); lithium chloride; lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Microwave irradiation; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 6 h / 60 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Microwave irradiation; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 6 h / 60 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Microwave irradiation; Inert atmosphere | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 6 h / 60 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Microwave irradiation; Inert atmosphere |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / methanol / 6 h / 60 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide; lithium chloride / water; 1,4-dioxane / 12 h / 110 °C / Microwave irradiation; Inert atmosphere | ||
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / methanol / 6 h / 60 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 1 h / 110 °C / Inert atmosphere; Microwave irradiation 3: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Inert atmosphere; Microwave irradiation | ||
Multi-step reaction with 3 steps 1: copper; potassium carbonate / dibutyl ether / 24 h / Reflux; Inert atmosphere 2: toluene-4-sulfonic acid / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere; Microwave irradiation 3: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: copper; potassium carbonate / dibutyl ether / 24 h / Reflux; Inert atmosphere 2: toluene-4-sulfonic acid / 1,4-dioxane / 6 h / 60 °C / Inert atmosphere; Microwave irradiation 3: tris-(dibenzylideneacetone)dipalladium(0); ruphos; lithium tert-butoxide / water; 1,4-dioxane / 12 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With [RuH2(η4-9-methylacridine){P(C6H11)3}2]; hydrogen In cyclohexane at 80℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate; acetic anhydride In 1,2-dichloro-ethane at 110℃; for 20h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridinium chlorochromate 2: triethylamine / 110 °C 3: morpholine / ethanol / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridinium chlorochromate 2: triethylamine / 110 °C 3: morpholine / ethanol / 0.5 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridinium chlorochromate 2: triethylamine / 110 °C 3: piperidine / ethanol / 45 - 55 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With copper(l) iodide In 1,2-dichloro-ethane at 65℃; for 12h; Inert atmosphere; Sealed tube; | |
92% | With copper(l) iodide In 1,2-dichloro-ethane at 65℃; Sealed tube; Inert atmosphere; | 1 Example 1 Preparation of 9-methylacridine (Formula (II)) Method I: diphenyliodonium trifluoromethanesulfonate (1 mmol, 429 mg), cuprous iodide (0.1 mmol, 19 mg)In a 25 mL sealed tube, a magnet was added and replaced with high purity nitrogen gas three times. To the tube was added o-acetophenone (1 mg, 121.6%),Dichloroethane, tighten the tube, move it into an oil bath of 65 ° C and stir, and react overnight. The reaction was monitored by TLC. After the reaction was completed, the tube was cooled to room temperature. 5 mL of distilled water was added to the system, stirred; extracted with ether (5 mL of X3). The organic phase was separated and the solvent was removed by rotary evaporator to obtain the crude product. The crude product was supported on silica gel and the eluent was purified by column chromatography with petroleum ether: ethyl acetate = 7: 1.9-methylacridine as a yellow solid, isolated in 92% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 6 h 2.1: sodium; 2-nitropropane / methanol; dimethyl sulfoxide / 20 °C 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C 3.2: 13 h / -10 - 20 °C | ||
Multi-step reaction with 3 steps 1.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 1.2: 4 h / 60 - 80 °C 2.1: 4 h / Reflux 3.1: sodium hydride / mineral oil; tetrahydrofuran / 20 °C / Cooling with ice | ||
Multi-step reaction with 3 steps 1.1: 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / 60 °C 1.2: 4 h / Reflux 2.1: 4 h / Reflux 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With tetrahydroxyborate; water at 80℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 2,6-di-tert-butyl-pyridine In dichloromethane at 20℃; for 3h; | General procedure for the synthesis of 10-methylacridiniumtrifluoromethanesulphonate derivatives (9-14) General procedure: To a solution of 1 mmol of an acridine derivative in 10 mL dry dichloromethane were added 4 mmol 2,6-ditert-butylpyridine and 5 mmol methyl trifluoromethanesulphonate. The solution was stirred at room temperature for 3 h. The precipitate was filtered off and washed with dichloromethane. The filtrate was evaporated under vacuum at room temperature to 5 mL and diluted with diethyl ether. The precipitate was filtered and vacuum dried. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With zinc(II) chloride at 130℃; for 3h; | General procedure for the synthesis of 9-[(E)-2-(nitrophenyl)ethenyl]acridine 6a, b General procedure: A mixture of 9-methylacridine (5) (1.0 g, 5.17 mmol),appropriate aldehyde (0.782 g, 5.17 mmol), and zincchloride (0.776 g, 5.70 mmol) was heated at 130 °C for 3 h.The reaction mixture was cooled to room temperature andwas partitioned between aqueous sodium hydroxide andchloroform. The organic phase was washed with water andbrine, dried over magnesium sulfate, filtered, and concentratedin vacuo. The residue was purified by silica gelcolumn chromatography (4:1 hexane-acetone) to producecompound 6 (Tsukamoto et al. 2009). 9-[(E)-2-(4-nitrophenyl)ethenyl]acridine (6a) Yield 1.12mg, 66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86 %Spectr. | With tert.-butylhydroperoxide In water at 20℃; for 18h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 2-aminopyridine; palladium(II) trimethylacetate; oxygen; citric acid In toluene at 110℃; for 18h; | |
With 2-aminopyridine; palladium(II) trifluoroacetate; oxygen; citric acid In toluene at 100℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 2.5 h / Reflux 2.1: ethanol / 1 h / Reflux 2.2: 12 h / Reflux 3.1: hydrazine hydrate; palladium on activated charcoal / ethanol / 12 h / Reflux; Inert atmosphere 4.1: dmap / tetrahydrofuran / 0.5 h / Cooling with ice 4.2: 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 2.5 h / Reflux 2.1: ethanol / 1 h / Reflux 2.2: 12 h / Reflux 3.1: hydrazine hydrate; palladium on activated charcoal / ethanol / 12 h / Reflux; Inert atmosphere 4.1: dmap / tetrahydrofuran / 0.5 h / Cooling with ice 4.2: 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 2.5 h / Reflux 2.1: ethanol / 1 h / Reflux 2.2: 12 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: selenium(IV) oxide / 1,4-dioxane / 2.5 h / Reflux 2.1: ethanol / 1 h / Reflux 2.2: 12 h / Reflux 3.1: hydrazine hydrate; palladium on activated charcoal / ethanol / 12 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With copper(II) bis(trifluoromethanesulfonate) In 1,1,2,2-tetrachloroethane at 100℃; for 14h; Sealed tube; | |
85% | Stage #1: 2-aminoacetophenone; phenylboronic acid With copper diacetate In 2,2,2-trifluoroethanol at 20℃; for 12h; Stage #2: With t-butyl bromide In 2,2,2-trifluoroethanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 9-methyl-acridine With chlorosulfonic acid at 100℃; for 12h; Cooling with ice; Stage #2: With water; sodium carbonate at 70℃; for 1h; Stage #3: triethylamine | 21 Example 21 Example 21 Synthesis of 9,10-dimethyl-3,6-disulfoacridin-10-ium 9-methylacridine (0.5 g) was placed in a 250 mL flask and immersed in an ice bath. 1.2 mL of chlorosulfonic acid (1.2 mL) was added dropwise and the mixture was stirred to obtain a clear, orange-brown solution. A reflux condenser was attached and the flask was heated to 100° C. for 12 h. The mixture was then cooled in an ice bath and quenched by addition of 25 g of crushed ice. The mixture was filtered, and the solid precipitate washed on the filter with 25 mL of ice water. The solid was collected and transferred to a flask with 25 mL of 200 mM sodium carbonate, then heated to 70° C. with stirring for 1 h forming a clear, brown solution. The water was removed by evaporation, and the solid purified by HPLC eluting with 25 mM triethylammonium acetate and acetonitrile which was evaporated to yield 0.9 g of the triethylammonium salt of 9-methyl-3,6-disulfoacridine. ESI MS calculated [M+H]=354.1 Da for C14H12NO6S2+, found 354.3 Da. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylsilane; potassium <i>tert</i>-butylate / neat (no solvent) / 18 h / 130 °C 2: air / 336 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylsilane; potassium <i>tert</i>-butylate / 18 h / 130 °C 2: air / 336 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylsilane; potassium <i>tert</i>-butylate / 18 h / 130 °C 2: air / 336 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylsilane; potassium <i>tert</i>-butylate / 18 h / 130 °C 2: air / 336 h | ||
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; Et3SiD / 18 h / 130 °C 2: air / 336 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With oxidant; oxidation catalyst at 80 - 100℃; for 1.8h; Microwave irradiation; | 1-3 Example 3 Step 1: weigh out 19.3g of 9-methylacridine, 72.1g of oxidant, 1.6g of oxidation catalyst, and 154.4g of solvent; Step 2: Divide 9-methylacridine into three parts, the first part is 9-methylacridine 6.4g, the second part is 9-methylacridine 6.4g, and the third part is 9-methylacridine 6.5g. Put the oxidant, oxidation catalyst, and solvent into the container and stir for 10 minutes. Then add the first portion of 9-methylacridine under stirring, stir for 30 minutes and heat to 80 °C by 350w microwave, and react for 1 hour under stirring. Then, the temperature was lowered to 40°C, and the second portion of 9-methylacridine was added under stirring, and heated to 90 °C by 350w microwave, and reacted for 0.5h under stirring. Then, the temperature was lowered to 40 °C, the third portion of 9-methylacridine was added under stirring, and the mixture was heated to 100 °C by 350w microwave, and reacted for 0.3h under stirring to obtain a reaction solution containing acridine 9-carboxylic acid. Step 3: Cool the reaction solution to room temperature and filter to obtain crude acridine 9-carboxylic acid. Add 3-5 times the weight of ethanol to the crude acridine 9-carboxylic acid, heat to reflux for 1.5-3 hours, then cool to room temperature, complete recrystallization, and obtain a mixed solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With acetic anhydride; acetic acid; at 50℃;Inert atmosphere; | 9-Methylacridine (1.5 mmol), acetic anhydride (1.5 mL) and acetic acid (3 mL) were stirred and heated in a round bottom flask equipped with a reflux condenser.When the temperature reached around 50C, the aldehyde substrate TSCHO (5-(4-(diphenylamino)phenyl)thiophene-2-carbaldehyde, 1 mmol) was added to the mixture; the mixture was then stirred at reflux under nitrogen overnight.After cooling, the resulting mixture was neutralized with sodium carbonate and extracted with dichloromethane, the organic layer was dried over sodium sulfate and evaporated in vacuo.The solid was further chromatographed on silica gel to give pure product (E)-4-(5-(2-(acridin-9-yl)ethenyl)thiophen-2-yl)-N,N-diphenyl Aniline (TSA), orange solid, 61% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With acetic anhydride; acetic acid at 50℃; Inert atmosphere; | 3 Example 3:Preparation of (E)-9-(2-(5'-(4-(diphenylamino)phenyl)-[2,2'-bithiophene]-5-yl)vinyl)-10- methylacridine-10-onium, trifluoromethanesulfonate (TSSAM) 9-Methylacridine (1.5 mmol), acetic anhydride (1.5 mL) and acetic acid (3 mL) were stirred and heated in a round bottom flask equipped with a reflux condenser.When the temperature reached around 50°C, the aldehyde substrate TSSCHO (5'-(4-(diphenylamino)phenyl)-[2,2'-bithiophene]-5-carbaldehyde, 1 mmol) was added to the mixture; then The mixture was stirred at reflux under nitrogen overnight.After cooling, the resulting mixture was neutralized with sodium carbonate and extracted with dichloromethane, the organic layer was dried over sodium sulfate and evaporated in vacuo.The solid was further chromatographed on silica gel to give pure product (E)-4-(5'-(2-(acridin-9-9-yl)ethenyl)-[2,2'-bithiophene]- 5-yl)-N,N-diphenylaniline (TSSA), red solid, 78% yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With acetic anhydride; acetic acid at 50℃; Inert atmosphere; | 1 Example 1: Preparation of (E)-9-(4-(diphenylamino)styryl)-10-methylacridine-10-onium, trifluoromethanesulfonate (TAM) 9-Methylacridine (1.5 mmol), acetic anhydride (1.5 mL) and acetic acid (3 mL) were stirred and heated in a round bottom flask equipped with a reflux condenser.When the temperature reached around 50°C, the aldehyde substrate TCHO (4-diphenylaminobenzaldehyde, 1 mmol) was added to the mixture; the mixture was then stirred at reflux under nitrogen overnight.After cooling, the resulting mixture was neutralized with sodium carbonate and extracted with dichloromethane, the organic layer was dried over sodium sulfate and evaporated in vacuo.The solid was further chromatographed on silica gel to give pure product (E)-4-(2-(acridin-9-yl)vinyl)-N,N-diphenylaniline (TA) as a yellow solid , the yield was 72%. |
Tags: 611-64-3 synthesis path| 611-64-3 SDS| 611-64-3 COA| 611-64-3 purity| 611-64-3 application| 611-64-3 NMR| 611-64-3 COA| 611-64-3 structure
[ 904886-12-0 ]
Benzo[h]quinoline-2-carbaldehyde
Similarity: 0.81
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :