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CAS No. : | 57134-53-9 | MDL No. : | MFCD07777106 |
Formula : | C9H6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XMXCRJLWEKHZAV-UHFFFAOYSA-N |
M.W : | 146.14 | Pubchem ID : | 92680 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.44 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.64 cm/s |
Log Po/w (iLOGP) : | 2.3 |
Log Po/w (XLOGP3) : | 2.18 |
Log Po/w (WLOGP) : | 1.48 |
Log Po/w (MLOGP) : | 1.72 |
Log Po/w (SILICOS-IT) : | 2.53 |
Consensus Log Po/w : | 2.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.52 |
Solubility : | 0.438 mg/ml ; 0.003 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.2 |
Solubility : | 0.92 mg/ml ; 0.00629 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.21 |
Solubility : | 0.899 mg/ml ; 0.00615 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.21 |
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 |
---|---|---|
95% | With n-butyllithium; In tetrahydrofuran; cyclohexane; | b 5-Ethynyl-benzo[1,3]dioxole To a solution of 5-(2,2-dibromo-vinyl)-benzo[1,3]dioxole (1.47 g, 5.0 mmol) in THF (10 mL) at -78 C. was added 2.0 M solution of n-butyllithium (5.5 mL, in cyclohexane) over 5 minutes period. After the addition completed, the reaction was stirred for 1 h, and then quenched with saturated NH4Cl. The mixture was allowed to warm up to room temperature. THF was removed. The aqueous was extracted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluding with DCM/hexane (5 to 10%) to give the title compound (0.64 g, 95% yield) as an orange oil. 1H NMR (CDCl3) delta7.02 (dd, 1H, J=1.6, 8.1 Hz), 6.93 (d, 1H, J=1.6 Hz), 6.75 (d, 1H, J=8.0 Hz), 5.98 (s, 2H), 2.97 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 2h; | To a solution of (benzo[d][1,3]dioxol-5-ylethynyl)trimethylsilane (3.77 g, 17.27 mmol) in THF (35 mL) was added tetrabutylammonium fluoride solution (19.00 ml, 1M in THF). After addition, the reaction was stirred at ambient temperature for 2 h. All the volatile solvent was removed under reduced pressure, and the residue was dissolved in DCM (20 ml). Water (15 mL) was added, and the aqueous layer was extracted with DCM (15 mL X 2). The combined organic layer was washed with brine (30 mL), dried over Na2SO4, and filtered. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography, by column chromatography with hexane/ethyl acetate (20/1, v/v) to obtain the compound 42 as a brown solid (1.74 mg, 98% yield): 1H NMR (400 MHz, CDCl3) _ 7.00 (dd, J = 8.0, 1.6 Hz, 1H), 6.91 (d, J = 1.6 Hz, 1H), 6.71 (d, J = 8.0 Hz, 1H), 5.92 (s, 2H), 2.98 (s, 1H); 13C NMR (100 MHz, CDCl3) _ 148.3, 147.4, 126.8, 115.2, 112.0,108.4, 101.4, 83.6, 75.7. |
88.46% | With methanol; potassium carbonate; | General procedure: The halogen containing molecule was reacted with3 equivalents of ethynyltrimethylsilane having PdC12 (PPh3)2 (0.03-0.05 equivalent), Cul (0.03-0.05 equivalent) as catalyst and Et3N as base in DMF at room temperature under N2 atmosphere for 3 h to overnight via the Sonogashira reaction. Afier extraction with diethyl ether or EtOAc and purified by column chromatography, 1 M of TBAF in THF or K2C03 in CH3OH was added to desilylation. The crude product was purified by column chromatography to give terminal alkyne products. |
86% | With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 0.5h;Inert atmosphere; | Compound 9 (5 g, 22.9 mmol) was dissolved in 80 ml of tetrahydrofuran under argon, and tetrabutylammonium fluoride (722 mg, 2.29 mmol) was added, and the mixture was reacted at room temperature for 0.5 hour.The reaction was monitored by TLC until compound 9 was completely reacted.The reaction was concentrated under reduced pressure to remove the tetrahydrofuran.The residue was reconstituted with diethyl ether and washed with 1 M diluted hydrochloric acid and brine.The ether layer was dried over anhydrous sodium sulfate and the solvent was evaporated.The crude product was purified by flash silica gel column eluting with petroleum etherThere was obtained 2.9 g of a colorless oily compound 5 in a yield of 86%. |
84% | With methanol; potassium carbonate; In dichloromethane; at 0 - 20℃; for 27h; | A single-neck flask was charged with 9.1 grams of 11 (41.68 mmol) followed bymethanol (50 ml) and methylene chloride (50 ml) and potassium carbonate (8.64 grams, 62.52mmol, 1.5 equivalents). The reaction mixture was initially maintained at 0 C and then warmedto room temperature. TLC analysis indicated greater than 60 % completion after 3 hours,however the reaction was left to stir for 24 hours at room temperature at which time reaction wascomplete. The reaction was worked up by concentration in vacuo and submitted to flashchromatography using straight hexanes to afford compound weighing 5.1 g. Yield is 84%. |
75% | With potassium carbonate; In methanol; at 20℃; for 1h;Inert atmosphere; | To a screw cap vial were added 11d (88.0 mg, 403 mumol), K2CO3 (167 mg, 1.21 mmol) and MeOH (2.1 mL) at rt and stirred for 1 h. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporation. The residue was diluted with EtOAc (40 mL), and washed with water (30 mL) and brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concentrated by rotary evaporation. Purification by column chromatography (petroleum ether) yielded 9d (44.1 mg, 75%) as a pale yellow liquid. |
With potassium carbonate; In tetrahydrofuran; methanol; at 20℃; for 2h; | Step 1: Preparation of 5-ethynylbenzo[d][1,3]dioxole To a solution of (benzo[d][1,3]dioxol-5-ylethynyl)trimethylsilane (10.0 g, 45.8 mmol) in methanol (80 mL) and tetrahydrofuran (80 mL) was added potassium carbonate (12.6 g, 91.6 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (80 mL*2). The combined organic layers were washed with brine (60 mL*2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 5-ethynylbenzo[d][1,3]dioxole (5.8 g, 39.7 mmol, 88%) as a yellow oil. This material was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetrakis(triphenylphosphine) palladium(0); triethylamine; In acetonitrile; for 4h;Reflux; | General procedure: To a solution of 1 (1.79 g, 12.2 mmol) and 2b (2.50 g, 11.1 mmol) in CH3CN (50 mL) were added Pd(PPh3)4 (642 mg, 0.556 mmol) and NEt3 (25 mL). The reaction mixture was stirred at reflux temperature for 4 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The crude product was purified by column chromatography on silica gel eluting with 40-50% CHCl3/n-Hexane and then 8% EtOAc/n-Hexane to afford 3b as a yellow powder (2.38 g, 88%): mp 111.5-112.0 oC; 1H NMR (300 MHz, CDCl3, delta): 2.48 (d, J = 0.9 Hz, 3 H), 6.01 (s, 2 H), 6.80 (d, J = 8.1 Hz, 1 H), 6.90 (d, J = 0.9 Hz, 1 H), 7.01 (d, J = 1.6 Hz, 1 H), 7.13 (dd, J = 8.1, 1.6 Hz, 1 H); MS (ESI) m/z 244 [M+H]+, 100% |
With triethylamine;tetrakis(triphenylphosphine) palladium(0); In acetonitrile; for 4h;Heating / reflux; | Triethylamine (25 ml), tetrakis(triphenylphosphine)palladium (642 mg), and 5-ethynyl-benzo(1,3)dioxole (1.79 g) were added to a solution of 2-iodo-4-methylthiazole (2.50 g) in acetonitrile (50 ml), and then the mixture was stirred for 4 hours under reflux condition. After the solvent was evaporated, the resultant residue was purified by silica gel flash column chromatography using a mixed solvent of ethyl acetate and chloroform and hexane to yield the title compound (2.38 g). 1H- NMR (300 MHz, CDCl3) delta ppm: 2.49 (3H, d, J = 0.9Hz), 6.01 (2H, s), 6.81 (1H, d, J = 8.1Hz), 6.91 (1H, d, J = 0.9Hz), 7.01 (1H, d, J =1.6Hz), 7.13 (1H, dd, J = 8.1, 1.6Hz) mp: 111.5-112.0C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | To a solution of acetylene 4 (2.74 g, 18.75 mmol) in 18 mL dry toluene was added at -78 0C 8.33 mL of a solution of nBuLi in hexanes (2.25 M1 18.75 mmol). The solution was stirred for 10 minutes before 18.75 mL of a solution of Me2AICI (1.0M in CH2Cb1 18.75 mmol) was added dropwise. The reaction flask was allowed to warm to room temperature and stir for 1 h. The reaction flask was then cooled to -20 0C and 18 mL of a solution of epoxide 3 (3.16 g, 9.38 mmol) in toluene was added dropwise over 20 min. The reaction was stirred at -20 0C for 3.5 h before being place in an ice bath and allowed to slowly warm to room temperature and stir for 12h. The reaction was cooled in an ice bath and quenched with 1 M HCI. Ethyl acetate (200 mL) was added and the layers where separated. The aqueous phase was extracted 3 x 100 mL EtOAc and the combined organic layers dried over Na2SO4. Concentration under reduced pressure and purification by flash column chromatography (hexanes:ethyl acetate, 7:1 to 4:1) afforded alcohol intermediate which was immediately subjected to protection protocol (2.01 g, 44%); [Q]22D -113.05 (c 0.5, CHCI3); Rf 0.30 (hexanes:ethyl acetate 2:1); IR (film) v 3491 , 2988, 1163 cm"1; 1H NMR (300 MHz1 CDCI3) delta: 7.78 (d, J = 8.1 Hz1 2H), 7.38 (d, J = 8.1 Hz, 2H)1 6.91 (dd, J = 8.2 Hz, 1.8 Hz 1 H)1 6.83 (d, J = 1.5 Hz1 1 H), 6.73 (d, J = 7.9 Hz, 1 H), 5.97 (s, 2H), 4.47 (d, J = 6.4 Hz, 1 H), 4.22 (dd, J = 6.1 , 4.4 Hz, 1 H)1 3.98 (m, 1H)1 3.40 (d, J = 6.4 Hz, 1 H), 3.24 (m, 2H), 3.06 (d, J = 9.6 Hz, 1H), 2.47 (s, 3H), 1.49 (s, 3H), 1.32 (s, 3H) ppm; 13C NMR (75 MHz, CDCI3) delta: 148.1 , 147.5, 145.7, 134.2, 130.4, 128.1 , 126.4, 116.2, 111.8, 110.3, 108.6, 101.5, 84.2, 83.8, 75.4, 70.1 , 68.7, 42.3, 40.5, 31.1 , 27.4, 25.2, 21.9 ppm; HRMS (FAB M+) calcd for C25H25NO7S 484.1430, found 484.1428. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | To compound 12 (0.400 mg, 2.739 mmol) in tetrahydrofuran (15 ml) stirring at - 78 C was added a 1.6M solution of n-butyllithium (n-BuLi)in hexanes (3.43 ml, 2.0 equivalents). The reaction was warmed to 0 Cfor 45 minutes and then recooled to - 78 C before addition of allyl chloroformate (1.32 g/1.16ml, 10.96 mmol, 4.0 equivalents) drop-wise over 10 minutes. The reaction was allowed to warmtowards room temperature overnight (12 hours) and then quenched with aqueous ammoniumchloride. (Monitoring of reaction after 4 hours via TLC showed complete consumption ofstarting material). The aqueous layer was extracted with ethyl acetate (3 × 100 mL) and thecombined organic layers were washed with brine, dried over anhydrous sodium sulfate, filteredand then concentrated in vacuo to a crude oil. The reaction was purified by silica gel column chromatography using a gradient mobile phase of hexanes/EtOAc (100:0 to 95:5) to provide 120mg of the product. Final yield of the product is 75 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In dichloromethane; chloroform; for 5h;Reflux; | To a solution of 1 (3.95 g, 27.0 mmol) and 2a (4.22 g, 25.7 mmol) in CHCl3 (50 mL) were added PdCl2(PPh3)2 (181 mg, 0.258 mmol), CuI (49 mg, 0.26 mmol), and NEt3 (25 mL). The reaction mixture was stirred at reflux temperature for 5 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The residue was diluted with EtOAc (300 mL) and washed with water (100mL) and brine (100 mL). The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 2-10% EtOAc/n-Hexane to afford 3a as a brown powder (4.11 g, 70%): 1H NMR (300 MHz, CDCl3, delta): 6.02 (s, 2 H), 6.82 (d, J = 8.1 Hz, 1 H), 7.03 (d, J = 1.7 Hz, 1 H), 7.14 (dd, J = 8.1, 1.7 Hz, 1H), 7.36 (d, J = 3.4 Hz, 1H), 7.84 (d, J = 3.4 Hz, 1 H); MS (ESI) m/z 230 [M+H]+, 100%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With tetrakis(triphenylphosphine) palladium(0); triethylamine; In acetonitrile; for 4h;Reflux; | General procedure: To a solution of 1 (1.79 g, 12.2 mmol) and 2b (2.50 g, 11.1 mmol) in CH3CN (50 mL) were added Pd(PPh3)4 (642 mg, 0.556 mmol) and NEt3 (25 mL). The reaction mixture was stirred at reflux temperature for 4 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The crude product was purified by column chromatography on silica gel eluting with 40-50% CHCl3/n-Hexane and then 8% EtOAc/n-Hexane to afford 3b as a yellow powder (2.38 g, 88%): mp 111.5-112.0 oC; 1H NMR (300 MHz, CDCl3, delta): 2.48 (d, J = 0.9 Hz, 3 H), 6.01 (s, 2 H), 6.80 (d, J = 8.1 Hz, 1 H), 6.90 (d, J = 0.9 Hz, 1 H), 7.01 (d, J = 1.6 Hz, 1 H), 7.13 (dd, J = 8.1, 1.6 Hz, 1 H); MS (ESI) m/z 244 [M+H]+, 100% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine; In tetrahydrofuran; at 20℃; for 2h; | To a solution of 1 (975 mg, 6.68 mmol) and 2d (1.08 g, 4.45 mmol) in THF (12 mL) were added Pd(PPh3)4 (257 mg, 0.222 mmol), CuI (85 mg, 0.45 mmol), and NH(i-Pr)2 (675 mg, 6.67 mmol). The reaction mixture was stirred at room temperature for 2 h. Water (60 mL) was added to the reaction mixture and the reaction mixture was extracted with EtOAc (20 mL, 2×50 mL). The combined organic layer was washed with brine (60 mL), dried over MgSO4, and concentrated. The crude product was purified by column chromatography on silica gel eluting with 7% EtOAc/n-Hexane and then 50% CHCl3/n-Hexane to afford 3d as a light yellow powder (1.00 g, 73%): 1H NMR (300 MHz, CDCl3, delta): 6.02 (s, 2 H), 6.82 (d, J = 8.1 Hz, 1 H), 7.00 (d, J = 1.6 Hz, 1 H), 7.13 (dd, J = 8.1, 1.6 Hz, 1 H), 7.23 (s, 1 H); MS (ESI) m/z 308 [M+H]+, 10%, 310 [M+2+H]+, 10%, 330 [M+Na]+, 20%, 332 [M+2+Na]+, 20%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With tetrakis(triphenylphosphine) palladium(0); triethylamine; In acetonitrile; for 4h;Reflux; | General procedure: To a solution of 1 (1.79 g, 12.2 mmol) and 2b (2.50 g, 11.1 mmol) in CH3CN (50 mL) were added Pd(PPh3)4 (642 mg, 0.556 mmol) and NEt3 (25 mL). The reaction mixture was stirred at reflux temperature for 4 h. The reaction mixture was filtered through Celite and the filtrate was evaporated. The crude product was purified by column chromatography on silica gel eluting with 40-50% CHCl3/n-Hexane and then 8% EtOAc/n-Hexane to afford 3b as a yellow powder (2.38 g, 88%): mp 111.5-112.0 oC; 1H NMR (300 MHz, CDCl3, delta): 2.48 (d, J = 0.9 Hz, 3 H), 6.01 (s, 2 H), 6.80 (d, J = 8.1 Hz, 1 H), 6.90 (d, J = 0.9 Hz, 1 H), 7.01 (d, J = 1.6 Hz, 1 H), 7.13 (dd, J = 8.1, 1.6 Hz, 1 H); MS (ESI) m/z 244 [M+H]+, 100% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: A 1.65 M solution of BuLi in hexane (0.30 mL, 0.50 mmol) was added to a solution of phenylacetylene (51 mg, 0.50 mmol) in THF (1.2 mL) at room temperature, and the mixture was stirred at that temperature for 2 min. A solution of (E)-8a (28 mg, 0.10 mmol) in THF (0.8 mL) was added to the resultant solution at room temperature, and the reaction mixture was stirred at that temperature for 30 min. The reaction was quenched with sat. aq. NH4Cl (1 mL), and the mixture was extracted with CHCl3 (3×5 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel [Rf = 0.13(hexane-AcOEt, 200:1)] to give (Z)-10a (24.4 mg, 0.080 mmol, 80%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With (-)-2-(2-(diphenylphosphino)naphthalen-1-yl)-1-(perfluorobenzyl)-4,5-diphenyl-1H-imidazole; copper(I) bromide; In dichloromethane; at -20℃; for 22h; | The scope of the reaction was studied and it was found that the reaction works exceedingly well over a broad range of substrates. Most notably, a variety of alkynes worked in the reaction including aryl, silyl, alkyl, and ester substituted acetylenes. Note the highlighted functional groups in the Table 4.2 below. This is highly useful and it is also noteworthy that with most other ligands, only a single type of alkyne functions well in the reaction. StackPhos is exceptional in this regard with even alkyl-substituted alkynes functioning quite well. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.01% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In water; tert-butyl alcohol; at 20℃; | General procedure: i-(2-Azidoethyl)piperidine (0.0641 g, 0.42 mmol) from method A was reacted with 5-ethynyl-iH- indole (0.0499 g, 0.35 mmol) in a ito 1 ratio of t-BuOH and water with CuSO4*5H20 (0.0050 g, 0.02 mmol) and sodium ascorbate (0.0158 g, 0.08 mmol) as catalyst. The reaction was stirred at room temperature for 5 h. Afier that, the reaction mixture was extracted with CH2C12. The crude product was purified by column chromatography (EtOAc) to give a pale yellow solid compound (68.86%). FTIR (ATR) (cm?) 3318, 3148, 3083, 2924, 1480, 1469, 1452, 1438, 1346, 1225, 1121, 1054, 892, 795, 771, 745; ?H-NMR (500 MHz, DMSO-d5) oe 8.41 (s, iH), 8.00 (dd, J=i.6, 0.8 Hz, iH), 7.58 (dd, J=8.4, 1.5 Hz, iH), 7.44 (d, J=8.4 Hz, iH), 7.36 (dd, J=2.9, 2.2 Hz, iH), 6.50-6.44 (m, iH), 4.48 (t, J=6.5 Hz, 2H), 2.76 (t, J=6.5 Hz, 2H), 2.47-2.34 (m, 4H), 1.48 (dt, J=iO.8, 5.6 Hz, 4H), 1.42-1.33 (m, 2H); ?3C-NMR (126 MHz, DMSO-d5) oe 147.7, 135.6, 127.8, 126.0, 122.0, 120.3, 119.0, 116.7, 111.7, 101.4, 57.8, 53.8, 47.0, 25.5, 23.9; mp=i48-i49 C.; HRMS calculated (C17H21N5, MH)296.1871, found 296.1871. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.46% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; at 20℃; | General procedure: i-(2-Azidoethyl)piperidine (0.0641 g, 0.42 mmol) from method A was reacted with 5-ethynyl-iH- indole (0.0499 g, 0.35 mmol) in a ito 1 ratio of t-BuOH and water with CuSO4*5H20 (0.0050 g, 0.02 mmol) and sodium ascorbate (0.0158 g, 0.08 mmol) as catalyst. The reaction was stirred at room temperature for 5 h. Afier that, the reaction mixture was extracted with CH2C12. The crude product was purified by column chromatography (EtOAc) to give a pale yellow solid compound (68.86%). FTIR (ATR) (cm?) 3318, 3148, 3083, 2924, 1480, 1469, 1452, 1438, 1346, 1225, 1121, 1054, 892, 795, 771, 745; ?H-NMR (500 MHz, DMSO-d5) oe 8.41 (s, iH), 8.00 (dd, J=i.6, 0.8 Hz, iH), 7.58 (dd, J=8.4, 1.5 Hz, iH), 7.44 (d, J=8.4 Hz, iH), 7.36 (dd, J=2.9, 2.2 Hz, iH), 6.50-6.44 (m, iH), 4.48 (t, J=6.5 Hz, 2H), 2.76 (t, J=6.5 Hz, 2H), 2.47-2.34 (m, 4H), 1.48 (dt, J=iO.8, 5.6 Hz, 4H), 1.42-1.33 (m, 2H); ?3C-NMR (126 MHz, DMSO-d5) oe 147.7, 135.6, 127.8, 126.0, 122.0, 120.3, 119.0, 116.7, 111.7, 101.4, 57.8, 53.8, 47.0, 25.5, 23.9; mp=i48-i49 C.; HRMS calculated (C17H21N5, MH)296.1871, found 296.1871. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 15h;Inert atmosphere; | To a screw cap vial were added azide 15 (68.4 mg, 219 mumol), alkyne 9d (48.0 mg, 328 mumol), CuI (20.9 mg, 110 mumol), and anhydrous DMF (0.44 mL) at rt. The reaction mixture was stirred at 80 C for 15 h. Upon completion of the reaction, the reaction mixture was cooled to rt. Purification by column chromatography (10:1 hexanes/EtOAc ? 20:1 CH2Cl2/MeOH) yielded 8d (54.0 mg, 54%) as an ivory solid. TLC: Rf 0.28 (20:1 CH2Cl2/MeOH). Mp: 271.3-273.3 C. 1H NMR (400 MHz, DMSO-d6): delta 11.83 (s, 1H), 10.68 (s, 1H), 9.14 (s, 1H), 8.44 (t, J = 2.0 Hz, 1H), 8.40 (d, J = 2.8 Hz, 1H), 7.99 (dm, J = 8.0 Hz, 1H), 7.96 (dd, J = 8.8, 2.8 Hz, 1H), 7.75 (dt, J = 8.0, 1.2 Hz, 1H), 7.55 (t, J = 8.0 Hz, 1H), 7.49-7.46 (m, 2H), 7.23 (d, J = 8.8 Hz, 1H), 7.05 (d, J = 8.0 Hz, 1H), 6.08 (s, 2H), 3.88 (s, 3H). 13C NMR (100 MHz, DMSO-d6): delta 166.0, 165.3, 158.3, 147.8, 147.2, 147.1, 138.7, 130.2, 129.3, 128.3, 125.3, 125.1, 124.7, 124.4, 121.2, 121.0, 119.3, 119.0, 119.0, 118.6, 108.8, 105.7, 101.2, 52.2. HRMS (ESI) m/z calcd for C24H19N4O6+ ([M+H]+) 459.1299, found 459.1295. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With hydrogen tetrachloroaurate(III) tetrahydrate; In 1,1,2,2-tetrachloroethane; at 50℃; for 15h;Inert atmosphere; Schlenk technique; Sealed tube; | General procedure: A flame-dried Schlenk tube was charged with N-benzyl-alpha,beta-unsaturated-gamma-lactam 1 (0.5 mmol). The tube was then transferred to a glove box, where it was charged with Broensted acid (0.05 mmol). The tube was removed from the glove box and attached to a Schlenk line, where it was charged with terminal alkyne 2 (1.5 mmol) and solvent (2.0 mL) via a syringe under a N2 atmosphere. The tube was then sealed and the reaction mixture was stirred at 50 C for 15 h. The reaction was cooled to room temperature and evaporated to dryness under vacuum to give a residue, which was purified by flash column chromatography over silica gel (EA:PE = 1:100 to 1:3, v/v) to afford the desired product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; for 24h; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol, 1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv)in dichloromethane (2 mL) and water (2 mL), were added CuSO4*5H2O (0.128 mmol, 0.064 equiv) andsodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then it wasadded a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane(3 x 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporatedunder reduced pressure. The products were purified by recrystallization from ethyl acetate. |
81% | With copper(II) sulfate hydrate; Erythorbic acid; In dichloromethane; water; for 24h;Inert atmosphere; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol,1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv) in dichloromethane (2 mL) and water (2 mL), were added CuSO4.5H2O pentahydrate (0.128 mmol, 0.064 equiv) and sodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then was added a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane (3 × 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The product was purified by recrystallization from ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; for 24h; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol, 1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv)in dichloromethane (2 mL) and water (2 mL), were added CuSO4*5H2O (0.128 mmol, 0.064 equiv) andsodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then it wasadded a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane(3 x 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporatedunder reduced pressure. The products were purified by recrystallization from ethyl acetate. |
90% | With copper(II) sulfate hydrate; Erythorbic acid; In dichloromethane; water; for 24h;Inert atmosphere; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol,1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv) in dichloromethane (2 mL) and water (2 mL), were added CuSO4.5H2O pentahydrate (0.128 mmol, 0.064 equiv) and sodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then was added a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane (3 × 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The product was purified by recrystallization from ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; for 24h; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol, 1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv)in dichloromethane (2 mL) and water (2 mL), were added CuSO4*5H2O (0.128 mmol, 0.064 equiv) andsodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then it wasadded a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane(3 x 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporatedunder reduced pressure. The products were purified by recrystallization from ethyl acetate. |
87% | With copper(II) sulfate hydrate; Erythorbic acid; In dichloromethane; water; for 24h;Inert atmosphere; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol,1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv) in dichloromethane (2 mL) and water (2 mL), were added CuSO4.5H2O pentahydrate (0.128 mmol, 0.064 equiv) and sodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then was added a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane (3 × 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The product was purified by recrystallization from ethyl acetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; for 24h; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol, 1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv)in dichloromethane (2 mL) and water (2 mL), were added CuSO4*5H2O (0.128 mmol, 0.064 equiv) andsodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then it wasadded a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane(3 x 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporatedunder reduced pressure. The products were purified by recrystallization from ethyl acetate. |
80% | With copper(II) sulfate hydrate; Erythorbic acid; In dichloromethane; water; for 24h;Inert atmosphere; | General procedure: To a solution of terminal acetylenes 25a-d (2 mmol,1.0 equiv) and azides 27a-d (2 mmol, 1.0 equiv) in dichloromethane (2 mL) and water (2 mL), were added CuSO4.5H2O pentahydrate (0.128 mmol, 0.064 equiv) and sodium ascorbate (0.352 mmol, 0.176 equiv). The reaction mixture was stirred for 24 h. Then was added a saturated solution of NH4Cl (30 mL) and the product was extracted with dichloromethane (3 × 20 mL). The organic phase was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The product was purified by recrystallization from ethyl acetate. |
80% | With copper(ll) sulfate pentahydrate; sodium L-ascorbate; In dichloromethane; water; for 24h;Inert atmosphere; | It was added CuSO4.5H2O pentahydrate (1.0 mmol, 0.249g) and sodium ascorbate (2.0 mmol, 0.396g) toa solution of terminal acetylene 7 (10 mmol, 1.46g) and azide 8 (10 mmol, 2.09g) in dichloromethane (10mL) and water (10 mL). The reaction mixture was stirred for 24 h. Then was added a saturated solutionof NH4Cl (150 mL) and the product was extracted with dichloromethane (3 x 50 mL). The organic phasewas dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. Theproduct was purified by recrystallization from ethyl acetate affording 6 (LASQUIM 25) in 80% yield(1.42g). 2. 4-(benzo[d][1,3]dioxol-5-yl)-1-(3,4,5-trimethoxyphenyl)-1H-1,2,3-triazole 6Spectra data in accordance with ref. [2]: 1H NMR (300 MHz, CDCl3) delta 3.87 (s, 3H, OCH3), 3.92 (s, 6H,2OCH3), 5.99 (s, 2H, CH2), 6.86 (d, 1H, J 8.0 Hz, Ar-H), 6.96 (s, 2H, Ar-H), 7.36 (m, 2H, Ar-H), 8.02 (s, 1H,*Tr-H); 13C NMR (75 MHz, CDCl3) delta 56.43, 61.03, 98.45, 101.24, 106.43, 108.70, 117.27, 119.57, 124.32,132.89, 138.32, 147.81, 148.18, 153.91. HRMS (ESI+) m/z calcd. for C18H17N3O5 [M + H]+: 356.1246; found:356.1253; *Tr: triazole hydrogen. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With potassium hydroxide; In toluene;Inert atmosphere; Reflux; | General procedure: To a solution of compounds 22a, 22b and 22c (47 mmol, 1.0 equiv) in toluene (353 mL), were added KOH (141 mmol, 3.0 equiv). The reaction was stirred under reflux in nitrogen atmosphere by 18 hours. Toluene was evaporated under reduced pressure, the residue diluted withethyl acetate (150 mL) and then, it was added a saturated solution of NH4Cl (100 mL). The products were extracted with ethyl acetate (3 × 100 mL) and washed with water(3 × 100 mL). After organic phase was dried over anhydrous MgSO4, the solvent was removed under reduced pressure and the residue purified by column chromatography onsilica gel using hexane/ethyl acetate as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With water; 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine; copper(I) bromide; ytterbium(III) triflate; In toluene; at 10℃; | General procedure: A mixture of CuBr (0.01 mmol, 0.1 equiv) and L1 (0.012 mmol, 0.12equiv) in toluene (1.0 mL) was stirred for 1 h at r.t., before 5a or 7 (0.1mmol, 1.0 equiv), phenylacetylene (2) (0.2 mmol, 2.0 equiv), and H2O(0.2 mmol, 2.0 equiv) were added successively. The mixture was cooled to 0 C and Yb(OTf)3 (0.1 mmol, 1.0 equiv) was added. After stirring for 12 h, a further quantity of a mixture of CuBr (0.005 mmol,0.05 equiv) and L1 (0.006 mmol, 0.06 equiv) in toluene (0.3 mL) was added, followed by 2 (0.1 mmol, 1.0 equiv) and Yb(OTf)3 (0.05 mmol,0.5 equiv). The resulting mixture was allowed to stir for 48-72 h at 0 C before the solvent was removed. The residue was purified by flash chromatography on silica gel saturated with Et3N (EtOAc-PE,2:98) to afford product 6 or 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium carbonate; In dimethyl sulfoxide; at 120℃; for 2h;Schlenk technique; | General procedure: In an oven-dried Schlenk tube terminal alkynes 4 (0.5 mmol),Pd/GO nano catalyst (5 mol%), K2CO3 (1 mmol) and solvent(DMSO) (1.0 mL) were added. The resulting reaction mixturewas stirred at 120 C for 2 h. The progress of the reactionwas monitored by TLC. After completion of reaction, thereaction mixture was allowed to cool to room temperature,then diluted with (? 10 mL) ethyl acetate and NH4Cl solution(? 10 mL) was added fallowed by extraction with ethylacetate. The organic layers were dried with Na2SO4 and concentratedin reduced vacuum. Purification of the residue bysilica gel column chromatography using distilled petroleumether/ethyl acetate as the eluent furnished the cinnamates andstilbenes. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; N-cyclohexyl-cyclohexanamine; In water; at 45℃; for 20h;Inert atmosphere; | General procedure: CuI (10mol%), 1 (1 equiv, 0.5mmol), and 2 (2 equiv, 1.0mmol) were sequentially added under air to a dram vial equipped with a stir bar. Amine (1.5 equiv, 0.75mmol), and distilled water (1.0mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 20hat the temperature, as shown in the tables. After this time, the contents of the flask were extracted with ethyl acetate and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Compound 4 (1 g, 4.37 mmol) was dissolved in 20 ml of tetrahydrofuran under argon.Bistriphenylphosphine dichloropalladium (0.22 mmol) and triethylamine (1.82 ml, 13.11 mmol) were added and stirred at room temperature for 10 min.Then, Compound 5 (958 mg, 6.66 mmol) and cuprous iodide (41.6 mg, 0.22 mmol) were added to the above reaction solution, and the mixture was reacted for 3 hours under heating at 70 C in an oil bath.The reaction was monitored by TLC until compound 4 was completely reacted.The reaction solution was filtered through celite, and the insoluble material was washed with ethyl acetate.The filtrate was spun dry, reconstituted with ethyl acetate, and washed with saturated ammonium chloride and brine.The ethyl acetate layer was dried over anhydrous sodium sulfate and evaporated.The crude product was purified by a flash silica gel column.913 mg of yellow solid compound 3 were obtained in a yield of 71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In toluene; at 20℃; | A combined suspension of methyl 4-amino-3-iodobenzoate (2.74 g, 9.90 mmol), copper (_) iodide (38 mg, 1.98 mmol), bis(triphenylphosphine)palladium(II) dichloride (139 mg, 1.98 mmol), and 5-ethynylbenzo[d][1,3]dioxole (1.74 g, 11.89 mmol) were stirred in toluene and TEA (1/1, 82 mL) at ambient temperature for overnight. The reaction solvent was evaporated under reduced pressure, and the residue was purified by column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain the compound 48 as a white solid (2.92 g, quant. yield): 1H NMR (400 MHz, CDCl3) _ 8.04 (d, J = 2.0 Hz, 1H), 7.78 (dd, J = 8.6 ,2.0 Hz, 1H), 7.03 (dd, J = 8.0, 1.6 Hz, 1H), 6.94 (d, J = 1.6 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 6.67 (d, J = 8.6 Hz, 1H), 5.97 (s, 2H), 4.74 (bs, 2H), 3.85 (s, 3H); 13C NMR (100 MHz, CDCl3) _ 166.7, 151.5, 148.1, 147.5, 134.3, 131.3, 126.2, 119.3, 116.1, 113.3, 111.4, 108.6, 107.2, 101.5, 95.1, 83.2, 51.8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (triphenylphosphine)gold(I) chloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In toluene at 20 - 70℃; for 3h; Inert atmosphere; | 1; 2; 3 Example 1 In a reaction flask with a water separator, under the protection of nitrogen,Put(triphenylphosphine) gold chloride(I) 1 g, trifluoromethanesulfonic anhydride34g and1,8-bisdimethylaminonaphthalene21 g was added to 200 mL of toluene and slowly heated to reflux.The water contained in the reaction system is removed by a water separator, and then cooled to room temperature.Dibromoacetonitrile20 g, heated again to reflux, to further remove water from the reaction system,Again to room temperature, under nitrogen protection,Quickly join5-alkynyl-benzo[d][1,3]dioxacyclopentene15g,Adding slowly to 70 ° C under nitrogen protection, the reaction is about 3 h,500 mL of water was added to the reaction solution, and heating was continued until reflux, and the reaction was continued for 5 hours.Adjust the pH to 4-5 with 1N hydrochloric acid solution, extract 100 mL of ethyl acetate and extract more reaction solution.The combined organic layers were washed several times with 100 mL of a saturated sodium chloride solution.Dry over anhydrous sodium sulfate, recover the solvent under reduced pressure, and purify the residue by column chromatography(eluent: V ethyl acetate: V petroleum ether = 1:5)3-(benzo[d][1.3]dioxol-5-yl)-4,4-dibromocyclobuten-2-one30.4g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.7 g | With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 17h;Inert atmosphere; | Step 2: Preparation of ethyl 5-(benzo[d][1,3]dioxol-5-yl)isoxazole-3-carboxylate To a solution of 5-ethynylbenzo[d][1,3]dioxole (5.8 g, 39.7 mmol) in N,N'-dimethylformamide (60.0 mL) was added a solution of (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (5.9 g, 39.7 mmol) in N,N'-dimethylformamide (20 mL) dropwise over 40 min under nitrogen. After addition, the reaction mixture was heated to 90 C. and a solution of triethylamine (12.0 g, 119 mmol) in N,N'-dimethylformamide (20 mL) was added dropwise over 1 h. The reaction mixture was stirred at this temperature for 17 h and cooled to room temperature. The reaction mixture was diluted with ethyl acetate (50 mL), washed with water (60 mL*2) and brine (60 mL*2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, petroleum ether/ethyl acetate=20/1) to yield ethyl 5-(benzo[d][1,3]dioxol-5-yl)isoxazole-3-carboxylate (3.7 g, 14.1 mmol, 36%) as a yellow solid. LCMS (ESI) m/z: 262.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With zinc dibromide; In 1,2-dichloro-ethane; at 120℃; for 24h;Inert atmosphere; | R1 is methyl; R2 is hydrogen; R3 is hydrogen; R5 = oxymethylene Take compound 1-4 (0.25mmol, 36.2mg) dissolved in 1,2-dichloroethane (0.25ml), add ZnBr2 (11.3mg, 0.05 mmol) and compound 5-2 (0.75mmol), use N2 protection System and stir at 120C for 24h. The reaction mixture was concentrated under reduced pressure, the crude product was separated by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 30: 1 (v/v) to obtain the final product, white solid; yield: 58% (42.2 mg ); |
Tags: 57134-53-9 synthesis path| 57134-53-9 SDS| 57134-53-9 COA| 57134-53-9 purity| 57134-53-9 application| 57134-53-9 NMR| 57134-53-9 COA| 57134-53-9 structure
[ 769-30-2 ]
Benzo[d][1,3]dioxol-4-ylmethanol
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[ 49763-96-4 ]
1-(Benzo[d][1,3]dioxol-5-yl)-4,4-dimethylpent-1-en-3-ol
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[ 2373-80-0 ]
3-(Benzo[d][1,3]dioxol-5-yl)acrylic acid
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[ 4421-09-4 ]
3,4-(Methylenedioxy)benzonitrile
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[ 61683-99-6 ]
5-(4-Methyl-1,3-dioxolan-2-yl)benzo[d][1,3]dioxole
Similarity: 0.71
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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.
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