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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: m-PEG3-Tos
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 62921-74-8 |
Formula : | C14H22O6S |
M.W : | 318.39 |
SMILES Code : | O=S(C1=CC=C(C)C=C1)(OCCOCCOCCOC)=O |
Synonyms : |
m-PEG3-Tos
|
MDL No. : | MFCD06200731 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
70% | EXAMPLE 10; [0115] 2-Hydroxy-3-(3,6,9-trioxadecyloxy)benzonitrile (18).; Compound 17 (5.3 g, 39.2 mmol) was added to a suspension of 60percent NaH (3.13 g, 78.2 mmol) in <n="69"/>DMSO (60 mL) using oven-dried glassware. After the reaction mixture was stirred at room temperature for 1 h, 15 (12.49 g, 39.22 mmol) in DMSO (25 mL) was introduced. After 24 h of stirring at room temperature, the reaction mixture was poured with stirring into cold water (100 mL) and was extracted with CHCl3 (3 X 100 mL). The aqueous phase was acidified to pH ~ 1 with 6 N HCl and was extracted with CHCl3 (5 X 60 mL). The latter CHCl3 extracts were concentrated in vacuo. Purification using column chromatography by gravity eluting with 10percent CH3OH/CHC13 gave 7.84 g of 18 (70percent) as an oil: 1H NMR delta 3.40 (s, 3 H), 3.58-3.62 (m, 2 H), 3.65-3.73 (m, 4 H), 3.75-3.78 (m, 2 H), 3.83-3.87 (m, 2 H), 4.14-4.18 (m, 2 H), 6.79-6.85 (m, 1 H), 7.09 (dd, 1 H, J = 7.8, 1.6), 7.15-7.18 (m, 1 H), 8.6 (s, 1 H); 13C NMR delta 57.25, 67.76, 67.85, 68.79, 68.92, 69.06, 70.36, 98.38, 115.44, 116.55, 118.51, 123.13, 145.98, 149.46; HRMS mlz calcd for C14H20NO5, 282.134 (M + H); found, 282.135. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; | (5-(2-(2-(2-methoxyethoxy)ethoxy)ethylamino)-l,3-phenylene)dimethanol: [300] To the mixture of the tosylate 249a (1.85 g, 5.81 mmol) and aniline compound 26 (1.78g, 11.6 mmol) in anhydrous DMF (9 mL) was added anhydrous potassium carbonate (1.61 g, 11.6 mmol). The mixture was heated to 85 0C and stirred at that temperature overnight. The solution was cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane. The filtrate was evaporated and the residue was diluted with dichloromethane and filtered again to remove the additional solid. The filtrate was evaporated and the residue was purified by silica gel chromatography (dichloromethane/methanol) to give compound 249b as a light yel]owish oil (835 mg, yield = 48percent). 1H NMR (400 MHz, CDCl3): delta 6.60 (s, IH), 6.47 (s, 2H), 4.48 (s, 4H), 4.31 (bs, IH), 3.66- 3.59 (m, 8H), 3.55-3.52 (m, 2H), 3.36 (s, 3H), 3.24 (t, J = 4.8 MHz, 2H); 13C NMR (400 MHz, CDCl3): delta 148.5, 142.4, 114.6, 110.7, 71.8, 70.4, 70.3, 70.1, 69.4, 64.9, 58.9, 43.5; MS (m/z): found 322.2 (M + Na)+. |
With potassium carbonate; In N,N-dimethyl-formamide; for 20h;Reflux; | A mixture of <strong>[71176-54-0](5-amino-1,3-phenylene)dimethanol</strong> (11.78 g, 77 mmol), 2-(2-(2-methoxyethoxyl)ethoxy)ethyl 4-methylbenzenesulfonate (15.3 g, 48.1 mmol), and potassium carbonate (13.28 g, 96 mmol) in DMF (96 ml) was refluxed for 20 hours. The reaction was cooled to ambient temperature and diluted with dichloromethane. The mixture was filtered through celite and concentrated in vacuo. The resulting orange oil was dissolved in dichloromethane (240 ml) and t-butyldimethylsilyl chloride (18.09 g, 120 mmol) and imidazole (9.80 g, 144 mmol) were added. The reaction was stirred at ambient temperature for 20 hours upon which it was diluted with dichloromethane and filtered through celite. Purification by silica gel chromatography (EtOAc/Hex) yielded 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxyl)ethoxy)ethyl)aniline (13 g, 52percent). 1H NMR (400 Hz, CDCl3): delta6.52 (s, 1H), 6.40 (s, 2H), 4.56 (s, 4H), 3.60 (t, 2H, J=5.2 Hz), 3.56 (m, 6H), 3.46 (m, 2H), 3.29 (s, 3H), 3.20 (t, 2H, J=5.2 Hz), 0.84 (s, 18H), 0.00 (s, 12H). MS (m/z): found 550.1 (M+Na)+. See FIG. 46. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A 100 gallon glass lined reactor was charged with 2,3- dihydroxybenzonitrile (4) and dimethyl sulfoxide. A 300 gallon glass lined reactor was charged with potassium tert-butoxide and dimethyl sulfoxide. The <strong>[67984-81-0]2,3-dihydroxybenzonitrile</strong> solution was slowly charged over 1 hour to the potassium tert-butoxide solution maintaining the temperature at <50°C. The reaction mixture was agitated. 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4- methylbenzenesulfonate (3) was charged over a 1 hour period to the reaction mixture. The reaction mixture was agitated for 2 hours and sampled for reaction completion analysis by HPLC. The reaction was quenched by charging USP water and agitating for 1 hour. The product was isolated first by washing the reaction mixture twice with methyl t-butyl ether. 6N HC1 was charged to the aqueous mixture. The product was then extracted twice with methylene chloride. The organic layers (product layers) were combined and the solvent was exchanged into ethanol by vacuum distillation. A 30percent sodium hydroxide solution was charged to the product dissolved in ethanol. Methyl t-butyl ether was added to help completely precipitate the product. The product was isolated by vacuum filtration. The wet cake was dried for over 15 hours in a tumble drier at 40°C. The reaction yielded sodium 2-cyano-6-(2-(2-(2-methoxyethoxy)ethoxy) ethoxy)phenolate (5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | To a round bottom flask was added <strong>[61367-62-2](4-bromo-3,5-dimethoxyphenyl)methanol</strong> (compound 10, 1.9 g, 7.69 mmol) and NN-dimethylformamide (20 mL). The solution was cooled to 0 °C and sodium hydride (0.383 g of 60percent (w/w) in mineral oil, 10 mmol) was added and the reaction was stirred for 1 hour at room temperature. 2-[2-(2- Methoxyethoxy)ethoxy] ethyl 4-methylbenzenesulfonate (2.8 mL, 9.23 mmol) was added and the reaction was stirred for six hours at room temperature. The reaction was quenched with water and concentrated in vacuo. The residue was taken up in ethyl acetate and washed using water, then brine. The organic layer was dried using sodium sulfate, filtered and concentrated in vacuo. The resulting oil was purified on silica gel using ethyl acetate and hexanes as eluent. Product l-(4-Bromo-3,5-dimethoxyphenyl-2,5,8,l l-tetraoxadodecane (17, 3.02 g, quant, yield) was isolated as a clear oil. LC-MS: TR=2.08 min; m/z+23=4\5.0, 417.0. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.70 (s, 2 H) 4.48 (s, 2 H) 3.82 (s, 6 H) 3.57 (s, 4 H) 3.47 - 3.55 (m, 6 H) 3.39 - 3.45 (m, 2 H) 3.22 (s, 3 H). |
Tags: m-PEG3-Tos | Sulfonates | Aryls | Ethers | Organic Building Blocks | 62921-74-8
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Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
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Code | Phrase |
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P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
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P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
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P263 | Avoid contact during pregnancy/while nursing. |
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
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P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
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P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
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P350 | Gently wash with plenty of soap and water. |
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P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
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P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
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P402 | Store in a dry place. |
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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 |
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H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
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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 |
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H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
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H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
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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 |
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H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
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H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
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H341 | Suspected of causing genetic defects |
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H351 | Suspected of causing cancer |
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H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
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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 |
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H402 | Harmful to aquatic life |
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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 |
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