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Structure of 110480-82-5
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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.
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| CAS No. : | 110480-82-5 |
| Formula : | C12H13NO |
| M.W : | 187.24 |
| SMILES Code : | OC[C@@H](N)C1=C2C=CC=CC2=CC=C1 |
| English Name : | (S)-2-Amino-2-(naphthalen-1-yl)ethan-1-ol |
| MDL No. : | MFCD09253738 |
| GHS Pictogram: | |
| Signal Word: | |
| Hazard Statements: | |
| Precautionary Statements: | |
| Class: | |
| UN#: | |
| Packing Group: |
* 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 |
|---|---|---|
| 79% | With triethylamine In dichloromethane at 0℃; for 1.5h; | |
| 37% | With triethylamine at -20℃; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 97% | Stage #1: (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(naphthalen-1-yl)ethyl)-2-methylpropane-2-sulfinamide With hydrogenchloride In methanol at 20℃; for 3h; Stage #2: With sodium hydrogencarbonate In water | 4.6.1. (S)-2-Amino-2-(4-fluorophenyl)ethanol 1a General procedure: At first, (Rs,2S)-N-((tert-butyldimethylsilyloxy)-1-(4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide 8a (0.280 g, 0.749 mmol) was dissolved in MeOH (10 mL) and then HCl/MeOH (4 M, 2.0 mL) was added. The mixture was stirred at room temperature for 3 h. The solvent was removed under vacuum and the residue neutralized with saturated NaHCO3 (20 mL). The mixture was extracted with CH2Cl2/MeOH (10:1, 3 × 50 mL) and the organic phases dried (Na2SO4) and concentrated to give 0.11 g (93%) of (S)-2-amino-2-(4-fluorophenyl)ethanol as a white solid. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | With triethylamine In dichloromethane at -10℃; for 0.416667h; Inert atmosphere; | N2,N6-bis[(S)-2-hydroxy-1-(naphthalen-2-yl)ethyl]pyridine-2,6-dicarboxamide (9); General procedure: A solution of 2,6-pyridine-dicarbonyldichloride (152 mg, 0.745 mmol, 1 equiv) in 3.5 mL CH2Cl2 was added to a 100-mL round-bottom flask charged with (1S)-1-(2-naphthyl)-2-hydroxyethylamine (279 mg, 1.49 mmol, 2 equiv) in 14 mL of CH2Cl2 and Et3N (0.54 mL, 3.88 mmol, 5.2 equiv) at 0 °C under N2. The reaction mixture was a clear dark yellow solution, which was stirred for 1 h, and the reaction was complete with the disappearance of the starting material. Workup employed 10 mL CH2Cl2 followed by 36 mL saturated NaHCO3. The aqueous layer was extracted with CH2Cl2, and combined organic layers were washed with brine. The combined organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography gave a yellow solid product (0.15 g, 40%) with Rf= 0.68 (85% EtOAc/hexanes); |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: (1S)-N-(tert-butoxycarbonyl)-1-(1-naphthyl)-2-hydroxyethylamine With hydrogenchloride In 1,4-dioxane at 20℃; Stage #2: With sodium hydrogencarbonate | (1S)-1-(2-Naphthyl)-2-hydroxyethylamine (4); General procedure: The white starting material 2 (0.1 g, 0.35 mmol, 1 equiv) was dissolved upon stirring in 2 mL of 4 M HCl in dioxane at room temperature, giving a clear light yellow solution. After 1 min, a light brownish yellow precipitate formed. The reaction mixture was allowed to stir until no starting material spot was observed on TLC. The reaction mixture was concentrated in vacuo to afford a pale-yellow solid, which was washed with saturated NaHCO3, and extracted with CH2Cl2. The combined extracts were dried over Na2SO4. The dried solution was filtered and concentrated, giving a pale yellow solid crude product, which has no need for further purification. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 61% | With zinc(II) chloride In chlorobenzene for 48h; Inert atmosphere; Reflux; | 2,2-Bis{2-[4(S)-1-naphthyl-1,3- (8); A solution of the corresponding naphthylamino alcohol (0.14 g, 0.76 mmol, 2 equiv) in PhCl was added to a flame-dried 50-mL 2-neck round-bottom flask charged with heat-fused ZnCl2 (0.31 g, 2.3 mmol, 6 equiv), and dimethylmalononitrile (0.036 g, 0.38 mmol, 1 equiv). The reaction mixture was then heated to reflux for 48 h. The resulting yellow solution was cooled to rt, and 12 mL of saturated NH4Cl was added with vigorous stirring, rendering the mixture homogeneous. The organic layer was collected, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography with 10% to 30% EtOAc/hexanes. The light yellow solid product (0.101 g, 61%) obtained was not very stable at room temperature (decomposition was observed, and the resulting mixture was purified once again by column chromatography to afford 82 mg of product). 13C NMR (125 MHz, CDCl3) δ 170.8, 139.9, 138.6, 134.1, 129.1, 128.1, 126.5, 126.0, 124.8, 123.7, 122.9, 75.6, 69.9, 39.5, 24.8. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 83% | With sodium tetrahydroborate In methanol at 0 - 20℃; for 24h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 0.25 g | Stage #1: carboxylic acid 1-(pyridin-2-yl)-1H-indole-2-carboxylic acid With triethylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-(S)-amino-2-(naphthalen-1-yl)ethanol In N,N-dimethyl-formamide at 20℃; for 36h; Stage #3: With triethylamine; p-toluenesulfonyl chloride In dichloromethane at 20 - 40℃; for 4.5h; | 13.2 (2) Synthesis of (S)-4-(1-naphthyl)-2-[1-(2-pyridyl)-1H-indol-2-yl]-4,5-dihydro-1,3-oxazole (Structural Formula L13): The carboxylic acid product with structural formula d (0.40 g, 1.70 mmol), the condensing agent N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)hexafluorophosphate urea (HATU) (1.94 g, 5.16 mmol), and N,N-dimethylformamide (DMF) 10 mL were added sequentially to a reactor. Then, triethylamine (TEA) (1.94 mL, 13.81 mmol) was added dropwise. After reacting at room temperature for 1 hour, (S)-2-amino-2-(naphthyl-1-yl)ethanol with structural formula 13e (0.48 g, 2.55 mmol) was added, and the reaction was carried out at room temperature for 36 hours. Add 10 mL of water, then extract three times with ethyl acetate (10 mL). The extracted organic phase was then washed three times with water (10 mL) to remove DMF, dried, concentrated, and subjected to column chromatography. Specific conditions were: a column packed with petroleum ether, with a petroleum ether:ethyl acetate ratio of 1:1 as the eluent, yielding a brown viscous liquid (0.59 g, 84% yield). In a reactor, the amide product with structural formula 13f (0.59 g, 1.43 mmol), p-toluenesulfonyl chloride (TsCl) (0.84 g, 4.29 mmol), 5 mL of dichloromethane, and triethylamine (TEA) (0.57 mL, 3.94 mmol) were added sequentially. The reaction was carried out at room temperature for 30 minutes, followed by dropwise addition of triethylamine (TEA) (2.40 mL, 17.47 mmol). A reflux condenser was attached, and the heating plate temperature was adjusted to 40 °C. Heating was stopped after 4 hours of reaction. Cool to room temperature, add 5 mL of water, then extract three times with dichloromethane (5 mL), followed by drying, concentration, and column chromatography. Specific conditions: column packed with petroleum ether, eluent of petroleum ether:ethyl acetate at a ratio of 4:1, yielding a powdery white viscous liquid (0.25 g, 44% yield). |
Tags: 110480-82-5 | (S)-2-Amino-2-(naphthalen-1-yl)ethan-1-ol | Chiral Building Blocks | Aryls | Alcohols | Amines | Other Chiral Nitrogen Ligands | Benzene Compounds | Organic Building Blocks | Asymmetric Synthesis | Chiral Nitrogen Ligands

A155172 [2829292-53-5]
(S)-2-Amino-2-(naphthalen-1-yl)ethanol hydrochloride
Reason: Free-Salt
Precautionary Statements-General | |
| Code | Phrase |
| P101 | If medical advice is needed,have product container or label at hand. |
| P102 | Keep out of reach of children. |
| P103 | Read label before use |
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| Code | Phrase |
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| P202 | Do not handle until all safety precautions have been read and understood. |
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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. |
| P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
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| 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. |
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| P281 | Use personal protective equipment as required. |
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| 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: |
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| P311 | Call a POISON CENTER or doctor/physician. |
| P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
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| P314 | Get medical advice/attention if you feel unwell. |
| P315 | Get immediate medical advice/attention. |
| P320 | |
| P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
| P321 | |
| P322 | |
| P330 | Rinse mouth. |
| P331 | Do NOT induce vomiting. |
| P332 | IF SKIN irritation occurs: |
| P333 | If skin irritation or rash occurs: |
| P334 | Immerse in cool water/wrap n wet bandages. |
| 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. |
| P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P342 | If experiencing respiratory symptoms: |
| P350 | Gently wash with plenty of soap and water. |
| P351 | Rinse cautiously with water for several minutes. |
| P352 | Wash with plenty of soap and water. |
| P353 | Rinse skin with water/shower. |
| P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
| P361 | Remove/Take off immediately all contaminated clothing. |
| P362 | Take off contaminated clothing and wash before reuse. |
| P363 | Wash contaminated clothing before reuse. |
| P370 | In case of fire: |
| 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: |
| P370 + P380 | In case of fire: Evacuate area. |
| 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. |
Storage | |
| Code | Phrase |
| P401 | |
| P402 | Store in a dry place. |
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| P404 | Store in a closed container. |
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| 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. |
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| P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
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Disposal | |
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| P501 | Dispose of contents/container to ... |
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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 |
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| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
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| 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 |
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