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CAS No. : | 2680-03-7 | MDL No. : | MFCD00008626 |
Formula : | C5H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YLGYACDQVQQZSW-UHFFFAOYSA-N |
M.W : | 99.13 | Pubchem ID : | 17587 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 28.77 |
TPSA : | 20.31 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.68 cm/s |
Log Po/w (iLOGP) : | 1.62 |
Log Po/w (XLOGP3) : | 0.31 |
Log Po/w (WLOGP) : | 0.26 |
Log Po/w (MLOGP) : | 0.38 |
Log Po/w (SILICOS-IT) : | -0.1 |
Consensus Log Po/w : | 0.49 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.52 |
Solubility : | 30.1 mg/ml ; 0.303 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.3 |
Solubility : | 49.8 mg/ml ; 0.502 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.3 |
Solubility : | 49.1 mg/ml ; 0.495 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.04 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P210-P264-P270-P280-P301+P310+P330-P302+P352+P312-P305+P351+P338+P310-P332+P313-P370+P378-P403+P235-P405-P501 | UN#: | 2810 |
Hazard Statements: | H227-H301+H311-H316-H318 | Packing Group: | Ⅲ |
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 |
---|---|---|
98% | at 70 - 100℃; for 8.5h; | A four neck flask equipped with a thermometer, stirrer, and cooler, was filled with 222.4 parts by weight of N- (2-aminoethyl)-3-aminopropyltrimethoxysilane, and the content of the flask was heated in A nitrogenous atmosphere to 70 C. Then, 109.0 parts by weight of N, N-dimethylacrylamide was added dropwise over 30 minutes, and the mixture was stirred and heated for 8 hours at 100 C. The reaction mixture was distilled under a reduced pressure at 130C and 1.3 hPa to produce 324.8 parts by weight of a yellowish transparent liquid, at a yield of 98 percent. Results of 13 C nuclear magnetic resonance spectral analysis (NM R), and infrared analysis (IR), defined the product as a nitrogen-containing organosilicon compound of the formula (C H3) 2N C O C2H4NH C2H4NH C3H6SI (O C H3) 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,5-dimethyl-2,5-di(2-ethyl hexanoyl peroxy)-hexane; at 75℃; for 2h; | A mix consisting of the prepolymer of Example 3, benzyl acrylate, <strong>[2495-37-6]benzyl methacrylate</strong> andN, N,-dimethylacrylamide at a weight ratio of 50/20/10/20 is prepared. To the mix is added Lupersol256 tu (Atochem) at 1 <Desc/Clms Page number 16>percent of the total weigh. The mix is then cured between two silane-treated glass plates in an oven at 75 C for 2 hours. The cured films are then released, extracted in isopropanol for over 4 hours and dried in a vacuum oven at 70 C overnight. All dried films are then placed in a borate buffered saline overnight before characterization. Films of different thickness can be made in this manner. To mimic actual uses, films of 600 to 1000 microns in thickness should be made and the UV-VIS transmittance measured. With 0.15 % by weight of dye moiety in the film, the UV-VIS transmittance should be less than approximately 50 to 60 percent at 450 nm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triethylamine; In acetonitrile; | A. (R)-5-trans-(2-N,N-Dimethylaminocarbonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole A mixture of N,N-dimethylacrylamide (134 muL, 1.3 mmol), tri-o-tolylphosphine (91 mg, 0.3 mmol), palladium (II) acetate (15 mg, 0.07 mmol), triethylamine (280 muL, 2 mmol) and <strong>[143322-57-0](R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole</strong> was dissolved in anhydrous acetonitrile (5 mL) and refluxed for 24 hours under nitrogen. The reaction was partitioned between ethyl acetate and aqueous sodium carbonate. The dried (Na2 SO4) organic phase was evaporated and the residue purified by column chromatography on silica gel, eluding with CH2 Cl2: MeOH: NH4 OH 96:3.5:0.5 to afford the title compound as a white foam (145 mg, 47%). Anal. Calcd for C19 H25 N3 O·1/9 CH2 Cl2: C, 71.56; H, 7.87; N, 13.10 %. Found: C,71.29; H,8.15; N,13.05. |
47% | With triethylamine; In acetonitrile; | A. (R)-5-trans-(2-N,N-Dimethylaminocarbonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole A mixture of N,N-dimethylacrylamide (134 muL, 1.3 mmol), tri-o-tolylphosphine (91 mg, 0.3 mmol), palladium (II) acetate (15 mg, 0.07 mmol), triethylamine (280 muL, 2 mmol) and <strong>[143322-57-0](R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole</strong> was dissolved in anhydrous acetonitrile (5 mL) and refluxed for 24 hours under nitrogen. The reaction was partitioned between ethyl acetate and aqueous sodium carbonate. The dried (Na2 SO4) organic phase was evaporated and the residue purified by column chromatography on silica gel, eluding with CH2 Cl2:MeOH:NH4 OH 96:3.5:0.5 to afford the title compound as a white foam (145 mg, 47%). Anal. Calcd for C19 H25 N3 O· 1/9CH2 Cl2: C,71.56; H,7.87; N,13.10%. Found: C,71.29; H,8.15; N,13.05. |
47% | With triethylamine; In acetonitrile; | A. (R)-5-trans-(2-N,N-Dimethylaminocarbonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole A mixture of N,N-dimethylacrylamide (134 muL, 1.3 mmol), tri-o-tolylphosphine (91 mg, 0.3 mmol), palladium (II) acetate (15 mg, 0.07 mmol), triethylamine (280 muL, 2 mmol) and <strong>[143322-57-0](R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole</strong> was dissolved in anhydrous acetonitrile (5 mL) and refluxed for 24 hours under nitrogen. The reaction was partitioned between ethyl acetate and aqueous sodium carbonate. The dried (Na2 SO4) organic phase was evaporated and the residue purified by column chromatography on silica gel, eluding with CH2 Cl2: MeOH: NH4 OH 96:3.5:0.5 to afford the title compound as a white foam (145 mg, 47%). Anal. Calcd for C19 H25 N3 O*1/9 CH2 Cl2: C,71.56; H,7.87; N,13.10%. Found: C,71.29; H,8.15; N,13.05. |
47% | With triethylamine; In acetonitrile; | A. (R)-5-trans-(2-N,N-Dimethylaminocarbonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole A mixture of N,N-dimethylacrylamide (134 muL, 1.3mmol), tri-o-tolylphosphine (91 mg, 0.3 mmol), palladium (II) acetate (15 mg, 0.07 mmol), triethylamine (280 muL, 2 mmol) and <strong>[143322-57-0](R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole</strong> was dissolved in anhydrous acetonitrile (5 mL) and refluxed for 24 hours under nitrogen. The reaction was partitioned between ethyl acetate and aqueous sodium carbonate. The dried (Na2 SO4) organic phase was evaporated and the residue purified by column chromatography on silica gel, eluding with CH2 Cl2: MeOH: NH4 OH 96:3.5:0.5 to afford the title compound as a white foam (145 mg, 47%). Anal. Calcd for C19 H25 N3 O·1/9 CH2 Cl2: C,71.56; H,7.87; N,13.10%. Found: C,71.29; H,8.15; N,13.05. |
47% | With triethylamine; In acetonitrile; | A. (R)-5-trans-(2-N,N-Dimethylaminocarbonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole A mixture of N,N-dimethylacrylamide (134 muL, 1.3 mmol), tri-o-tolylphosphine (91 mg, 0.3 mmol), palladium (II) acetate (15 mg, 0.07 mmol), triethylamine (280 muL, 2 mmol) and <strong>[143322-57-0](R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole</strong> was dissolved in anhydrous acetonitrile (5 mL) and refluxed for 24 hours under nitrogen. The reaction was partitioned between ethyl acetate and aqueous sodium carbonate. The dried (Na2 SO4) organic phase was evaporated and the residue purified by column chromatography on silica gel, eluding with CH2 Cl2: MeOH: NH4 OH 96:3.5:0.5 to afford the title compound as a white foam (145 mg, 47%). Anal. Calcd for C19 H25 N3 O. 1/9 CH2 Cl2: C, 71.56; H, 7.87; N, 13.10%. Found: C, 71.29; H, 8.15; N, 13.05. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 5: SYNTHESIS OF POLYMER-LINKED INHIBITORS WITH GRAFT COPOLYMERS: SYNTHESIS OF STAR COPOLYMER OF (1-ACRYLOYL-3- AMINOOXALYL-2-METHYL-1 H-lNDOL-4-YLOXY)-ACETIC ACID, N-BUTYL ACRYLATE, DIMETHYL ACRYLAMIDE, AND N-(2-ACRYLOYLAMINO-ETHYL)-ACRYLAMIDE.[00352] This example describes approaches for synthesizing a phospholipase inhibitor comprising an oligomer or polymer moiety covalently linked to an inhibiting moiety, where the polymer moiety is linked using graft copolymers. In particular, a scheme is provided for synthesis of a star copolymer of (1-Acryloyl-3-aminooxalyl-2-methyl-1 H-indol-4-yloxy)-acetic acid, n-butyl acrylate, dimethyl acrylamide, and N-(2-Acry.oylamino-ethyl)-acrylamide.[00353] The synthesis scheme and the polymer formed thereby can be represented by the schematic representation: <n="142"/>A mixture of 26, dimethyl acrylamide, and n-butyl acrylate in a mole ratio of 0.04 : 0.48 : 0.48 (in total 10 mmol) is dissolved in 20 ml_ of DMF. To the mixture AIBN (2,2'- azobisisobutyronitrile, 10 mmol % to compound 26) is added and is heated to 75 0C for 8 hours. To the resulted yellow solution 1 mmol of dimethyl acrylamide and ethylene bis- diacrylamide (1 :1 ) is added and stirred for an additional 8 hours. After the reaction is cooled to rt, the reaction mixture is precipitated twice, dried under reduced pressure to obtain the copolymer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate; In toluene; at 130℃; for 24h;Inert atmosphere; | General procedure: N-Benzoylsulfonamide 1a (27.5 mg, 0.1 mmol), [RhCl2Cp*]2 (1.2 mg, 0.002 mmol), and Cu(OAc)2·H2O (40.0 mg, 0.20 mmol) were loaded in a dry vial, which was subjected to evacuation/flushing with dry argon three times. Anhydrous toluene (1.0 mL) solution of tert-butyl acrylate 2a (17.4 muL, 0.12 mmol) was syringed into the mixture, which was then stirred at 130 C for 24 h or until the starting material had been consumed as determined by TLC. Upon cooling to room temperature, all volatiles were evaporated and the residue was purified by preparative TLC (ethyl acetate/hexane 1:2) to give isoindolinone 3a in 88% yield |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With triethylamine; In ethanol; at 20℃; for 48h; | To a stirred solution of 3-(mercaptopropyl) triethoxysilane (30 mmol) in 50 mL of anhydrous ethanol was added N,N-dimethylacrylamide (30 mmol) at ambient temperature. To the solution of reactants was added triethylamine (30 mmol) and resulting solution was stirred at ambient temperature for 48h. The mixture was concentrated under reduced pressure and dried overnight in Schlenk line. The product was obtained in 90% yield. The synthesized compound was characterized via 1H-NMR (400 MHz) and HPLC (88.4% purity). The chemical structures were characterized via NMR (400 MHz) as shown in Figure 1. |
90% | With triethylamine; In ethanol; | To a stirred solution of 3-(mercaptopropyl)triethoxysilane (30 mmol) in 50 mL of anhydrous ethanol was added N,N-dimethylacrylamide (30 mmol) at ambient temperature. To the solution of reactants was added triethylamine (30 mmol) and resulting solution was stirred at ambient temperature for 48 h. The mixture was concentrated under reduced pressure and dried overnight in Schlenk line. The product was obtained in 90% yield. The synthesized compound was characterized via 1H-NMR (400 MHz) and HPLC (88.4% purity). The chemical structures were characterized via NMR (400 MHz) as shown in . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; | EXAMPLE 4 Synthesis of poly (N,N-dimethylacrylamide-co-N-acryloyloxysuccinimide-co-N,N,N-trimethylaminoethylacrylamide). The synthetic path is the same as for [DMA98-co-NAS2]: N,N-dimethylacrylamide (600 mg, 6,15 mmols), N-acryloyloxysuccinimide (20.7 mg, 0.12 mmols) and N,N,N-trimethylaminoethylacrylamide (47 mg (0.3 mmols) in 6 ml of anhydrous tetrahydrofuran (THF). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | In a Shlenck reactor, to a solution of <strong>[40851-91-0]6-chloro-2-methoxy-3-nitropyridine</strong> (1.00 g, 5.30 mmol) in DMF (50 mL), 1VN-dimethylacrylamide (820.00 jiL, 7.96 mmol) and TEA (2.21 mL, 15.90 mmol) were added. The mixture was degassed under N2 and [1,1?- bis(diphenylphosphino)ferrocene] dichloropalladium (II), complex withdichloromethane (434.00 mg, 0.53 mmol) was added. The mixture was degassed again with N2 and stirred at 100 C overnight. The mixture was evaporated in vacuo. The residue was taken-up in EtOAc and brine and filtered on a pad of celite. The cake was washed with EtOAc. The layers were separated and the organic layer was washed with brine. The organic layer was dried over Mg504, filtered off and evaporated in vacuo togive a black solid. The residue (2.4 g) was purified by column chromatography on silica gel (irregular SiOH, 15-40 jim, 50 g, dry loading on celite, mobile phase:heptane/EtOAc/MeOH, gradient: from heptane 70%, EtOAc 27%, MeOH 3% to heptane 40%, EtOAc 54%, MeOH 6%). The pure fractions were combined and evaporated to dryness to give 566 mg of intermediate 154 (43% yield, orange solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); triethylamine; In N,N-dimethyl-formamide; at 140℃;Inert atmosphere; | In a microwave vial, a suspension of <strong>[34552-14-2]3-amino-2-bromo-5-methylpyridine</strong> (500.00 mg,2.67 mmol), N,N-dimethylacrylamide (689.00 jiL, 6.68 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine) palladium (II) dichloride (94.60 mg, 0.13 mmol) and TEA (1.12 mL, 8.02 mmol) in DMF (12.5 mL) was purged with N2 and was heated at 140 C using one single mode microwave (Biotage Initiator) with a power output ranging from 0 to 400 W for 30 mm [fixed hold time]. This reaction was performed in two batches from 500 mg of <strong>[34552-14-2]3-amino-2-bromo-5-methylpyridine</strong> each. These twobatches were combined and evaporated in vacuo. The residue was taken-up in EtOAc and water. The layers were separated and the aqueous layer was extracted twice with EtOAc and twice with DCM. The aqueous layer was saturated with K2C03 and extracted twice with a mixture of DCM/MeOH (9:1). The combined organic layers were dried over MgSO4, filtered off and evaporated in vacuo to give a brown solid. The residue (2.2 g) was purified by column chromatography on silica gel (irregular SiOH,15-40 jim, 80 g, dry loading on celite, mobile phase: heptane/(EtOAc/MeOH (9:1)), gradient: from 70:30 to 15:85). The pure fractions were combined to give 815 mg of intermediate 271 (71% yield, yellow solid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 100℃;Inert atmosphere; | To a stirred solution of 7-bromo-lH-indole (0.46 g, 2.3 mmol) in dry DMF (2.6 ml) was added N,N-dimethylacrylamide (0.46 g, 4.6 mmol) at room temperature. To this mixture Pd(OAc)2 (0.010 g, 0.04 mmol), triphenyl phosphine (0.024 g, 0.1 mmol), and diisopropylethyl amine (0.5 ml, 2.9 mmol) were added at room temperature. The reaction mixture was then purged with argon gas for 20 minutes. Then it was heated to 100 C overnight. The reaction mixture was poured into ice cold water (50 ml) and extracted with ethyl acetate (3 x 50 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous Na2S04 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford the title compound (0.43 g, 85%) as light brown solid. 1H NMR (400 MHz, DMSO-d6): d 2.97 (s, 3H), 3.20 (s, 3H), 6.50 (s, 1H), 7.05 (t, J = 7.6 Hz, 1H), 7.24 (d, J = 15.2 Hz, 1H), 7.38 (t, J = 2.8 Hz, 1H), 7.56 - 7.63 (m, 2H), 7.96 (d, J = 8.0 Hz, 1H), 11.53 (s, 1H, -NH). LCMS: m/z = 215.3 [M+l] |
Tags: 2680-03-7 synthesis path| 2680-03-7 SDS| 2680-03-7 COA| 2680-03-7 purity| 2680-03-7 application| 2680-03-7 NMR| 2680-03-7 COA| 2680-03-7 structure
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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.
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