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CAS No. : | 2974-94-9 | MDL No. : | MFCD00060666 |
Formula : | C12H9IO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BDKOUDYNKRCDEC-UHFFFAOYSA-N |
M.W : | 296.10 | Pubchem ID : | 520399 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 65.68 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.66 cm/s |
Log Po/w (iLOGP) : | 2.9 |
Log Po/w (XLOGP3) : | 4.86 |
Log Po/w (WLOGP) : | 4.08 |
Log Po/w (MLOGP) : | 4.14 |
Log Po/w (SILICOS-IT) : | 4.02 |
Consensus Log Po/w : | 4.0 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.24 |
Solubility : | 0.0017 mg/ml ; 0.00000576 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.79 |
Solubility : | 0.00482 mg/ml ; 0.0000163 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.59 |
Solubility : | 0.000752 mg/ml ; 0.00000254 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.51 |
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 |
---|---|---|
2.1% | EXAMPLE 1 A 500 ml three-necked glass flask was charged with 17.02 g (100 millimoles) of diphenyl ether, 25.38 g (100 millimoles) of iodine, 0.4 ml of 60% by weight nitric acid and 300 ml of dichloromethane. The flask was immersed in a hot water bath kept at 40 C. While the contents were fully stirred, nitrogen gas containing a predetermined amount of nitrogen dioxide was blown into the solution at a rate of 80 ml/min. During a total reaction period of 16 hours, the amount of nitrogen dioxide added was 10.95 g (238 millimoles). Analysis of the product by gas chromatography showed that the conversion of diphenyl ether was 100%, and 40.2 g (yield 95.2%) of 4,4'-diiododiphenyl ether, 1.1 g (yield 2.7%) of 2,4'-diiododiphenyl ether and 0.6 g (yield 2.1%) of 4-iododiphenyl ether were formed. The iodination yield (the yield of the iodo-aromatic compound based on the used iodine) was 99.0%. | |
0.4% | COMPARATIVE EXAMPLE 2 A 200 ml three-necked glass flask was charged with 8.51 g (50 millimoles) of diphenyl ether, 12.69 g (50 millimoles) of iodine, 2 ml of concentrated sulfuric acid, 50 ml of acetic acid, 15 ml of dichloromethane and 15 ml of water. The flask was immersed in a hot water bath kept at 60 C. While the contents were fully stirred, the reaction was carried out for 2 hours. The product was analyzed by gas chromatography. The conversion of diphenyl ether was 0.4%, and 4-iododiphenyl ether was formed in an amount of 0.06 g (yield 0.4%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In toluene; at 110℃; for 48h; | Example 2A 3-(4-phenoxyphenoxy)quinuclidine 3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 1-iodo-4-phenoxy-benzene (Aldrich, 296 mg, 1 mmol), Cul (Strem Chemicals, 19 mg, 0.1 mmol), 1,10-phenanthroline (Aldrich, 36 mg, 0.2 mmol), and Cs2CO3 (660 mg, 2.0 mmol) in toluene (anhydrous, Aldrich, 10 mL) and heated at 110 C. for two days. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2*10 mL). The organic phase was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:1, Rf. 0.20) as oil (220 mg, yield, 75%). 1H NMR (MeOH-d4, 300 MHz) delta 1.45-1.58 (m, 1H), 1.64-1.85 (m, 2H), 2.00-2.15 (m, 1H), 2.20-2.30 (m, 1H), 2.70-3.10 (m, 5H), 3.34-3.40 (m, 1H), 4.52 (m, 1H), 6.83-6.98 (m, 6H), 7.03 (tt, J=7.5, 1.0 Hz, 1H), 7.20-7.41 (m, 2H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. |
75% | With copper(l) iodide; 1,10-Phenanthroline; In toluene; at 110℃; for 48h; | Example 3A 3-(4-phenoxyphenoxy)quinuclidine 3-Hydroxy quinuclidine (Aldrich, 254 mg, 2 mmol) was treated with 1-iodo-4-phenoxy-benzene (Aldrich, 296 mg, 1 mmol), CuI (Strem Chemicals, 19 mg, 0.1 mmol), and 1,10-phenanthroline (Aldrich, 36 mg, 0.2 mmol) in toluene (anhydrous, Aldrich, 10 mL) and heated at 110 C. for two days. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2*10 mL). The organic phase was concentrated and the title compound was purified by chromatography (SiO2, CH2Cl2:methanol:NH3H2O, 90:10:1, Rf. 0.20) as oil (220 mg, yield, 75%). 1H NMR (MeOH-d4, 300 MHz) delta 1.45-1.58 (m, 1H), 1.64-1.85 (m, 2H), 2.00-2.15 (m, 1H), 2.20-2.30 (m, 1H), 2.70-3.10 (m, 5H), 3.34-3.40 (m, 1H), 4.52 (m, 1H), 6.83-6.98 (m, 6H), 7.03 (ft, J=7.5, 1.0 Hz, 1H), 7.20-7.41 (m, 2H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | Example 3A (R)-3-(4-phenoxyphenoxy)quinuclidine 3-(R)-Hydroxy-quinuclidine (the product of Reference Example 1, 152 mg, 1.2 mmol), was coupled with 1-iodo-4-phenoxy-benzene (178 mg, 0.6 mmol) according to the procedure of Example 3A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (25 mg, yield, 14%). 1H NMR (MeOH-d4, 300 MHz) delta 1.45-1.58 (m, 1H), 1.64-1.85 (m, 2H), 2.00-2.15 (m, 1H), 2.20-2.30 (m, 1H), 2.70-3.10 (m, 5H), 3.34-3.40 (m, 1H), 4.52 (m, 1H), 6.83-6.98 (m, 6H), 7.03 (tt, J=7.5, 1.0 Hz, 1H), 7.30 (t, J=7.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.2% | Example 4A (S)-3-(4-phenoxyphenoxy)quinuclidine 3-(R)-Hydroxy-quinuclidine (the product of Reference Example 1, 152 mg, 1.2 mmol), was treated with 1-iodo-4-phenoxy-benzene (178 mg, 0.6 mmol) according to the procedure of Example 3A to provide the title compound. (80 mg, yield, 45.2%). 1H NMR (MeOH-d4, 300 MHz) delta 1.45-1.58 (m, 1H), 1.64-1.85 (m, 2H), 2.00-2.15 (m, 1H), 2.20-2.30 (m, 1H), 2.70-3.10 (m, 5H), 3.34-3.40 (m, 1H), 4.52 (m, 1H), 6.83-6.98 (m, 6H), 7.03 (tt, J=7.5, 1.0 Hz, 1 H), 7.30 (t, J=7.5 Hz, 2H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | Preparation IX N-(4-phenoxyphenyl)phenylalanine A mixture of 2.17 g (7.3 mmol) of <strong>[2974-94-9]4-phenoxyiodobenzene</strong>, 1.02 g (6.2 mmol) of phenylalanine, 0.48 g of bis(tri-o-tolylpalladium) dichloride, 125 mg of cuprous iodide, 240 mg of benzyltriethylammonium chloride and 876 mg of potassium carbonate in 12 ml of dimethylformamide, 1.2 ml of water and 2.4 ml of triethylamine is prepared. This reaction medium is stirred at 100 C. for 24 h and then cooled. 50 ml of toluene are added and the mixture is concentrated under reduced pressure. The residue is taken up with 40 ml of ethyl acetate and 40 ml of water and the mixture is acidified to pH 2. The precipitate formed is filtered off, washed with 10 ml of water and 5 ml of ethyl acetate and then dried to give 640 mg of the expected product in the form of a fine gray solid (yield=30%). M.p.=194 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 9 1-(2-[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with <strong>[2974-94-9]4-iodophenyl phenyl ether</strong> (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta8.18 (s, 1 H), 8.12 (d, J=7.4 Hz, 1 H), 7.62 (d, J=7.7 Hz, 1 H), 7.41-7.47 (m, 3 H), 7.18-7.27 (m, 4 H), 7.06 (dd, J=7.6, 1.0 Hz, 2 H), 6.90 (dd, J=6.7 Hz, 2 H), 6.71 (s, 2 H), 4.85 (t, J=5.1 Hz, 2 H), 4.37 (s, 2 H), 4.02 (t, J=5.0 Hz, 2 H) IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1 | ||
Example 9 1-(2-[3-(4-Phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine Using the general method of Example 7, 1-[2-(2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.50 g, 1.88 mmol) was reacted with <strong>[2974-94-9]4-iodophenyl phenyl ether</strong> (0.78 g, 2.63 mmol). The crude product was purified by column chromatography eluding with 95/5 dichloromethane/methanol to provide a solid. The solid was slurried with aqueous sodium hydroxide to remove salts and then purified by column chromatography eluding with 9/1 ethyl acetate/methanol to provide a solid. This material was further purified by column chromatography eluding with 99/1 ethyl acetate/methanol to provide 24 mg of 1-(2-[3-(4-phenoxyphenyl)-2-propynyl]oxy}ethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 146-148 C. Analysis. Calculated for C27H22N4O2.(H2O)4/5: %C, 72.24; %H, 5.30; %N, 12.48. Found: %C, 71.82; %H, 4.85; %N, 12.35. 1H NMR (300 MHz, DMSO-d6) delta 8.18 (s, 1H), 8.12 (d, J=7.4 Hz, 1H), 7.62 (d, J=7.7 Hz, 1H), 7.41-7.47 (m, 3H), 7.18-7.27 (m, 4H), 7.06 (dd, J=7.6, 1.0 Hz, 2H), 6.90 (dd, J=6.7 Hz, 2H), 6.71 (s, 2H), 4.85 (t, J=5.1 Hz, 2H), 4.37 (s, 2H), 4.02 (t, J5.0 Hz, 2H); IR (KBr) 3444, 3070, 2928, 1500, 1230, cm-1; HRMS (EI) Calculated for C27H22N4O2 (M+) 434.1743, found 434.1748. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate;copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 92℃; for 5h; | Example 356: 3-[1-(4-phenoxyphenyl)-3-(2-phenylethyl)-1H-indol-5-yl]propanoic acid 2-amino-2-(hydroxymethyl)propane-1,3-diol salt (1:1); Step 1; To a solution of the compound obtained at Example 142 (15.30 g) in toluene (76 ml) were added <strong>[2974-94-9]4-iododiphenyl ether</strong> (28.18 g), copper(I) iodide (1.944 g), N,N'-dimethylethylenediamine (3.420 g) and tripotassium phosphate (21.186 g), and the mixture was heated and stirred at 92C for 5 hours. The reaction mixture was allowed to cool, then silica gel (15.3 g) was used to filter off the insolubles and the solvent was distilled off from the filtrate in vacuo to afford a crude product of ethyl 3-[1-(4-phenoxyphenyl)-3-(2-phenylethyl)-1H-indol-5-yl]propanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With copper diacetate; triethylamine; at 20℃; for 30h; | General procedure: To a flask containing a stirring mixture of triphenyltin chloride (0.5 mmol, 0.193 g) and phenol (1 mmol, 0.094 g) in triethylamine (10 equiv, 1.4 mL) at room temperature, copper acetate (40 mol%, 0.076 g) was added. Monitoring the reaction with TLC showed that the reaction was completed within 30 h. The reaction mixture was washed with HCl (1 N, 1 mL) to remove the excess of Et3N. Then, the catalyst was filtered and the aqueous solution was extracted with ethyl acetate (5×10 mL) and dried over anhydrous Na2SO4. The solvent was evaporated and column chromatography of the crude mixture on silica-gel using n-hexane/ethyl acetate (3/1) as eluent afforded biphenyl ether in 85% yield (0.130 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; iron(II) chloride; In chloroform; at 120℃; for 16h; | A 25 mL reaction flask was charged with ferrous chloride (0.05 mmol),4-phenoxy-iodobenzene (0.5 mmol),<strong>[90555-66-1]3-ethoxybenzeneboronic acid</strong> (0.75 mmol),Sodium carbonate (1.0 mmol),Cesium hydroxide monohydrate (2.5 mmol),Sodium iodide (0.251111] 100),(0.75_31),Chloroform (1.5_31) and polyethylene glycol-400 (2. (^),And reacted at 120 C for 16 h. Cooled to room temperature,extraction,The solvent was distilled off under reduced pressure, and the residue was isolated by column chromatography to give a yield of 91%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With cesiumhydroxide monohydrate; sodium carbonate; sodium iodide; Trimethylacetic acid; In ethylene glycol; at 120℃; for 24h; | Compound 4: 25 mL reaction flask was charged with 4-phenoxyiodobenzene (0.5 mmol), <strong>[90555-66-1]3-ethoxyphenylboronic acid</strong> (0.75 mmol), sodium carbonate (1.0 mmol), and cesium hydroxide monohydrate (2.5 mmol), sodium iodide (0.25 mmol), pivalic acid (0.75 mmol), chloroform (1.5 mmol) and ethylene glycol (2.0 g). Reacted at 120 C for 24 h. Cool to room temperature, extract, the solvent was evaporated under reduced pressure and then purified by column chromatography to yield a yield of 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 24h;Inert atmosphere; | 270.1 g (2.0 mol) of 4-aminopyrazolo[3,4-d]pyrimidine and 295.9 g (1.0 mol) of <strong>[2974-94-9]4-iododiphenyl ether</strong> were added to 1 L of DMSO.Thereafter, 448.8 g (4.0 mol) of potassium t-butoxide was added. After the addition was completed, the mixture was purged with nitrogen, heated to 120 C, and reacted for 24 hours.Upon completion of the HPLC, the end of the reaction was completed when the <strong>[2974-94-9]4-iododiphenyl ether</strong> was consumed.After cooling to room temperature, 5 L of methyl tert-butyl ether was added, followed by 3 washes with 5 L of water.The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure, the residue was purified by column chromatography on a conventional crude product obtained was recrystallized using DMF solvent to give3-(4-Phenoxyphenyl)-4-amino-1H-pyrazolo[3,4-d]pyrimidine (248.5 g, 82%, HPLC purity: 99.7%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate; In dimethyl sulfoxide; at 20℃; for 24h;Inert atmosphere; Sealed tube; | General procedure: A 10 mL flask was charged with a magnetic stir bar, CuI (19 mg,10 mol%), L2 (86 mg, 20 mol%), Cs2CO3 (651 mg, 2 mmol) and solid aryl iodides (1.0 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of Argon, DMSO (1.0 mL), 1.0 mmol aryl iodides (if liquid), 0.9 mL (12.0 mmol) aqueous ammonia (28%) were added by syringe slowly. The reaction mixture was allowed to stir under argon at room temperature for 24 h. Then the mixture was diluted with 30 ml dichloromethane and passed through a fritted glass filter, the filter cake being further washed with 15 ml dichloromethane, dried over Na2SO4, filtered and the most solvent was removed under vacuum. The residue was purified by column chromatography on silica gel with an eluent of petroleum ether and ethyl acetate. |
Tags: 2974-94-9 synthesis path| 2974-94-9 SDS| 2974-94-9 COA| 2974-94-9 purity| 2974-94-9 application| 2974-94-9 NMR| 2974-94-9 COA| 2974-94-9 structure
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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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