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CAS No. : | 628-99-9 | MDL No. : | MFCD00004593 |
Formula : | C9H20O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 144.25 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
98% | With potassium permanganate; iron(III) chloride In acetone at -78 - 0℃; for 4h; | |
97% | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; silica gel; potassium bromide In dichloromethane at 0℃; for 1h; | |
93% | With manganese(II) nitrate; C70H128N16O4; oxygen; cobalt(II) nitrate In acetic acid at 25℃; for 1h; |
92% | With jones reagent In acetone at 5℃; for 2.5h; | |
90% | With (tetrabutylammonium)4[Al4(H2O)10(β-SbW9O33H)2]*4H2O; dihydrogen peroxide In water; acetonitrile at 70℃; for 1h; | |
89% | With sodium periodate; RuCl3*2.9H2O In water at 20℃; for 0.25h; Sonication; | |
84% | With N-hydroxyphthalimide; oxygen; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 80℃; for 2h; | |
83% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In water; acetonitrile at 20℃; for 8h; Green chemistry; | General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. |
76% | With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); 2,6-dimethoxy-p-quinone; tetrabutylammonium tetrafluoroborate; acetic acid In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; Electrochemical reaction; | |
75% | With tert.-butylhydroperoxide; [((E)-1-(((2-hydroxypropyl)imino)methyl)naphthalen-2-olato)Cu(μ2-Cl)2Cu((E)-1-(((2-hydroxypropyl)imino)methyl)naphthalen-2-olato)]*1.5(methanol) In ethanol at 80℃; for 2h; | 2.4 Oxidation Procedure General procedure: To a solution of the alcohol (0.5 mmol) and complex (scheme 1; 0.01 mmol) in ethanol (5 mL) was added tBuOOH (0.5 mmol), and the reaction mixture was stirred in air at 80°C for the required time. GC monitored the reaction progress and the yields of the products. Further purification was achieved by silica chromatography. |
74% | With sodium hypochlorite; 3',3',4',4',5',5',6',6',7',7',8',8',8'-tridecafluorooctanoic acid (1-hydroxyl-2,2,6,6-tetramethylpiperidin-4-yl)-(3",3",4",4",5",5",6",6",7",7",8",8",8"-tridecafluorooctyl)-amide; potassium bromide In dichloromethane at 0℃; for 1h; aq. buffer; | |
74% | With sodium hypochlorite; 3',3',4',4',5',5',6',6',7',7',8',8',8'-tridecafluorooctanoic acid (1-hydroxyl-2,2,6,6-tetramethylpiperidin-4-yl)-(3",3",4",4",5",5",6",6",7",7",8",8",8"-tridecafluorooctyl)-amide; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0 - 20℃; for 1.33333h; aq. buffer; | |
67% | With [MnIII(2-((2-(2-(2-(2-hydroxybenzylideneamino)phenylamino)propylamino)phenylimino)methyl)phenolato)]Cl; dihydrogen peroxide In acetonitrile for 4.3h; Reflux; | |
60% | With C14H36Cu2N4O2(2+)*2CF3O3S(1-) In dichloromethane at -40.16℃; for 5h; Inert atmosphere; | 2.2 Oxidation of exogenous substrates General procedure: Solutions of OTMPDMeCN-(X)2 and OTMPDPhCN-(X)2 (10mM, 5mL in CH2Cl2) were prepared from the pre-mixed 1:1 Cu(I)-ligand precursors by addition of excess O2 (1atm) at 193K. Two equiv of substrate per oxidant were used unless otherwise noted. For anaerobic substrate oxidations, excess O2 was removed and the solution was flushed with N2 prior to substrate addition. Similar product distributions were obtained for alcohol oxidation reactions performed under O2 and N2 at 233K. Alcohol oxidations without NEt3 were carried out at 233K, and all other reactions were carried out under N2 at 193K unless otherwise noted. The resulting reaction mixtures were quenched by dropwise addition of aqueous ammonia (30%) until the CH2Cl2 layer turned colorless, and passed through a column of neutral activated alumina (Brockmann I, ∼150 mesh, 58Å) followed by MeOH (2mL). The copper product is retained, and the organic products elute. The reaction mixture was analyzed by GC/GC-MS. Mass recovery of the products was >90% based on addition of an internal calibrant (benzonitrile for alcohols, acetophenone for amines). |
With resting mycelia of Scedosporium sp. A-4 at 30℃; | ||
With chromic acid | ||
With nickel at 170℃; | ||
65 % Chromat. | With sodium hypochlorite; water; potassium bromide In dichloromethane at 0℃; for 0.5h; | |
100 % Chromat. | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen In acetic acid at 40℃; for 5h; | |
With 4,4-dimethyl-1-phenyl-1-penten-3-one; magnesium oxide at 193.85℃; for 3h; | ||
56 % Chromat. | With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Oxone; tetrabutylammomium bromide In toluene at 20℃; for 12h; | |
8 % Chromat. | With 1,4-dihydronicotinamide adenine dinucleotide; NAD In phosphate buffer at 30℃; for 72h; | |
With 5-chloro-7-iodo-8-quinolinolatomanganese(III) In water; acetone at 25℃; for 8h; | ||
With Sphingobium yanoikuyae alcohol dehydrogenase; NADP In water; dimethyl sulfoxide Enzymatic reaction; | ||
97 %Chromat. | With NADP; chloroacetone at 30℃; for 24h; Microbiological reaction; aq. buffer; | |
With oxygen In α,α,α-trifluorotoluene at 110℃; regioselective reaction; | ||
95 %Chromat. | With tert.-butylhydroperoxide; vanadia for 8h; | |
With Yarrowia lipolytica short chain dehydrogenase/reductase; nicotinamide adenine dinucleotide phosphate; magnesium chloride In aq. buffer at 28℃; for 0.166667h; Enzymatic reaction; | General procedure: Unless otherwise stated, purified tagged YlSDR (1-10μM) was assayed in 50mM Tris-HCl containing 2mM MgCl2, pH 8.0, 10mM substrate (for lipophilic substrates, additional 0.15% Tween 20) and 1mM NADP+ or NAD+. The increase of absorbance at 340nm was monitored at 28°C for 10min (or 12h for ribose). For NAD+, no activity was observed under these conditions. The reported values represent the average of at least four measurements with appropriate blanks substracted. One activity unit is defined as the amount of enzyme catalyzing the reduction of 1μM of NADP+ per minute. Kinetic parameters for oxidation were determined at pH 10.0 from unweighted non-linear least-square fits of experimental data using the program Sigmaplot (version 12.3). | |
With reusable unsupported rhenium nanocrystalline particle In neat (no solvent) at 180℃; for 10h; Green chemistry; | ||
With potassium hydrogencarbonate; potassium bromide In dichloromethane at 0℃; for 0.0833333h; | ||
99 %Chromat. | With C66H60Cl2N10P2Ru2(2+)*2Cl(1-); potassium <i>tert</i>-butylate In toluene for 24h; Reflux; Inert atmosphere; Schlenk technique; | |
8 %Spectr. | With (2,9-dimethyl-1,10-phenanthroline)-palladium(II) acetate; 2,6-dimethoxy-p-quinone; tetrabutylammonium tetrafluoroborate; acetic acid In dimethyl sulfoxide at 20℃; for 8h; Electrolysis; Inert atmosphere; | 2.5. Electrolysis General procedure: A homemade airtight electrolysis cell was used equipped with areticulated vitreous carbon (RVC) as working electrode (basi, USA),a bridged Ag/AgCl reference electrode with 2 M LiCl ethanol solution as inner solution and a 0.1 M Bu4NBF4 DMSO as bridge solution was used and the counter electrode, a platinum rod electrode, was put in a divided cell separated from the anodic partby a ceramic frit. In a typical electrolysis experiment 4 mL of a 0.2 MBu4NBF4 DMSO solution was added to the divided part followed bythe addition of 200 mL of acetic acid. In the anodic part neocuproinePd(OAc)2 (0.1 equivalent), 2,6-dimethoxybenzoquinone(0.6 equivalent) and the alcohol (0.7 mmol) was added to a 14 mL solution of 0.2 M Bu4NBF4 in DMSO. The cell was closed andput under an argon atmosphere. Stirring was started, next apotential of 0.7 V was applied. After the appropriate reaction time30 mL of water was added to the reaction mixture. The resultingmixture was extracted with tert-butylmethylether (3 times 25 mL).The collected organic layer was washed with 15 mL of water tofurther remove DMSO. Next the organic layer was dried withMgSO4 filtered and evaporated. The resulting solution wasexamined with NMR. Isolated products were obtained usingcolumn chromatography with heptane/ethylacetate (7/3) aseluent. |
39 %Chromat. | With tert.-butylhydroperoxide; 13H2O*O12V4(4-)*2C36H24N6Ru(2+) In acetonitrile at 60℃; for 6h; | |
61 %Chromat. | With tert.-butylhydroperoxide; 2C5H3N2O2(1-)*4.5C4H4N2*H(1+)*Cu(2+)*5Cu(1+)*6H2O*O62P2W18(6-) In acetonitrile at 60℃; for 3h; | |
52 %Chromat. | With K16H15Li7[Pr2(H2O)3(pyrazine-2,3-dicarboxylato)As3W29O103]2*38H2O; dihydrogen peroxide In water; N,N-dimethyl-formamide at 65℃; for 4h; | |
With acetone at 50℃; for 20h; Green chemistry; | ||
64 %Chromat. | With tert.-butylhydroperoxide; C6H7As4N4O140Ru4W40(20-)*4K(1+)*9Na(1+)*7H(1+)*42H2O In water at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium tetrahydroborate In various solvent(s) at 60℃; for 8h; | |
97% | With [biphenyl-2-O-Al(OiPr)-N(SO2C8H17)-2'] In dichloromethane; isopropyl alcohol at 25℃; for 5h; | |
89% | Stage #1: 2-Nonanone With diphenylsilane In toluene at 20℃; for 48h; Stage #2: With hydrogenchloride; methanol In toluene at 20℃; Further stages.; |
87.6% | With C47H45ClN2P2Ru; isopropyl alcohol; sodium hydroxide at 82℃; for 3h; Inert atmosphere; | |
With diethyl ether; water; sodium inactive form of nonanol-(2); | ||
With copper chromite at 150℃; Hydrogenation; | ||
With ethanol; sodium inactive form of nonanol-(2); | ||
With hydrogen at 150℃; | ||
With hydrogen at 178℃; for 6h; | ||
70 % Chromat. | With sodium diethylpiperidinohydroaluminate In tetrahydrofuran at 0℃; for 3h; | |
With sodium hydroxide; sodium tetrahydroborate; zinc 2-ethylhexanoate 1.) THF, reflux, 2.) 40 deg, 1 h; Yield given; Multistep reaction; | ||
With sodium tetrahydroborate; silica gel In hexane at 40℃; for 3h; Yield given; | ||
With potassium phosphate buffer; pig testicular 20β-hydroxysteroid dehydrogenase; NADPH at 37℃; | ||
With sodium tetrahydroborate | ||
With potassium hydroxide; gold on titanium oxide; isopropyl alcohol at 82℃; for 8h; Inert atmosphere; chemoselective reaction; | ||
96 %Chromat. | With C37H28Cl2N5PRu; isopropyl alcohol; sodium hydroxide at 82℃; for 0.5h; Inert atmosphere; | |
Stage #1: 2-Nonanone With (μ-(imidazol-2-ylidene)pyridine-CH2-(imidazol-2-ylidene)pyridine)[IrCp*Cl]2(PF6)2 In isopropyl alcohol for 0.0833333h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: With C3H7O(1-)*HNa In isopropyl alcohol for 12h; Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
acetate of levorotatory methyl-n-heptyl-carbinol; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With magnesium(II) perchlorate at 20℃; for 3h; | |
With triethylamine Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at -40 - 20℃; for 40h; Yield given. Yields of byproduct given; | ||
In tetrahydrofuran at -40 - 50℃; for 3h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 7-Aminoheptanoic acid hydrochloride With thionyl chloride at 30 - 35℃; for 0.5h; Stage #2: nonan-2-ol In chloroform for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cytochrome P450 BM3 from Bacillus megaterium 77-9H mutation; oxygen; NADPH In phosphate buffer; ethanol at 25℃; for 12h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HBr 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran | C.1 Catalytic Asymmetric Hydrogenation of non-1-en-2-yl Acetate Comparative Example 1 Catalytic Asymmetric Hydrogenation of non-1-en-2-yl Acetate This reaction was performed as in Example 1 with bis(cyclooctadienyl)rhodium tetrafluoroborate (10 mg; 0.025 mmol; 0.01 equiv), R,R-1,2-bis(2,5-dimethylphospholano)benzene (6, R"=CH3; 9 mg; 0.03 mmol; 0.012 equiv) and non-1-en-2-yl acetate (461 mg; 2.5 mmol) in 10 mL of degassed THF until hydrogen uptake ceased (2 h) to afford 0.46 g of crude product. 1 H NMR analysis indicated 2-nonyl acetate as the sole product, and chiral GC analysis and comparison to racemate indicated 64.0% ee for 2-nonyl acetate. Hydrolysis of the acetate to 2-nonanol and comparison of the optical rotation, [α]D24 -13.9° (c 1.15, benzene), with the literature value for the (S) enantiomer, [α]D18 +11.4° (c 1.30, benzene) (Mori, K.; Ogita, H. Leibigs Ann. Chem. 1994, 1065.), indicated the (R) configuration for 2-nonyl acetate. 1 H NMR (CDCl3) δ 4.886 (1H, m(6), J=6.93 Hz); 2.029 (3H, s); 1.6-1.2 (12H, m); 1.202 (3H, d, J=6.26 Hz); 0.879 (3H, t, J=6.53 Hz). Chiral GC (30 m Cyclodex-B column ›J&W[Scientific], 100° C.): tR (S) 9.634 min; tR (R) 10.395 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; dmap at 20℃; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida antarctica lipase B immobilized on acrylic resin catalyst at 20 - 25℃; for 8h; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With tris(2,4-pentanedionato)ruthenium(III); methanesulfonic acid; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 18h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cytochrome P450 BM-3 enzyme mutant 9-10A-F87A Enzymatic reaction; | 3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A. | |
With cytochrome P450 BM-3 enzyme mutant wt F87A Enzymatic reaction; | 3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;Inert atmosphere; | The alpha-(n-benzyl)-L-glutamate-N-alpha-benzylcarbonyl acid (5 g, 1 equiv.), 2-nonanol (2.92 g, 1,5 equiv.), EDCI (2.58 g, 1 equiv.), HOBT (1.82 g, 1 equiv.) and DMAP (1.65 g, 1 equiv.) are suspended in dichloromethane (100 ml). The reaction medium is stirred at room temperature overnight. The medium is successively washed with a 0.1N hydrochloric acid solution, a saturated sodium hydrogencarbonate solution and then with a saturated sodium chloride solution. The organic phase is dried on magnesium sulphate, filtered and concentrated in order to lead to a pale yellow oil which is then purified by chromatography on silica gel (heptane:ethyl acetate gradient (100:0 to 50:50) in order to lead to a yellow oil (2.65 g, yield 40%) which will be reengaged into stage 2. |
40% | With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;Inert atmosphere; | With magnetic stirring,A 250 ml one-necked flask placed under a nitrogen sweepAlpha- (n-benzyl) -L-glutamate-N-alpha-benzylcarbonylic acid(5 g, 1 eq),2-nonanol(2.92 g, 1.5 eq),EDCI(2.58 g, 1 eq),HOBT(1.82 g, 1 eq) andDMAP(1.65 g, 1 eq) was added toIt is suspended in dichloromethane (100 ml).The reaction medium is stirred overnight at room temperature.This medium0.1 N hydrochloric acid solution,Saturated sodium bicarbonate solution,Then,Wash sequentially with saturated sodium chloride solution.The organic phase was dried over magnesium sulfate,Filtered,Concentrate to give a pale yellow oil,It is then chromatographed on silica gel(From heptane: ethyl acetate gradient (100: 0 to 50: 50) to give a yellow oil (2.65 g, 40% yield)Place it again under Phase 2. |
Tags: 628-99-9 synthesis path| 628-99-9 SDS| 628-99-9 COA| 628-99-9 purity| 628-99-9 application| 628-99-9 NMR| 628-99-9 COA| 628-99-9 structure
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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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