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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: 2-Benzoylaniline
4.5
*For Research Use Only !
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 2835-77-0 |
Formula : | C13H11NO |
M.W : | 197.23 |
SMILES Code : | C1=C(C=CC=C1)C(C2=C(C=CC=C2)N)=O |
Synonyms : |
2-Benzoylaniline
|
MDL No. : | MFCD00007713 |
InChI Key : | MAOBFOXLCJIFLV-UHFFFAOYSA-N |
Pubchem ID : | 76080 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | 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 |
---|---|---|
85% | To a solution of benzyl proline (41 g, 0.2 mol) in methylene chloride (200 ml) was added thionyl chloride (18.34 ml, 0.25 mol) with stirring at -20 C to -30 C over a period of 10 min. The stirring was continued at -10 C until the reaction mixture became almost transparent. Then a solution of 2-aminobenzophenone (25 g, 0.125 mol) in methylene chloride (100 ml) was added to the reaction mixture at -30 C with stirring. The stirring was continued at ambient temperature for another 10 h and a solution of sodium carbonate (40 g) in water (150 ml) was added to the reaction mixture with stirring at 0 C. The organic layer was separated, the aqueous layer extracted several times with methylene chloride and the organic solutions were combined and evaporated. The product (benzyl proline-aminobenzophenone adduct) was crystallized from ethanol and was isolated in 85% yield. | |
77% | To a stirred solution ofcompound 10 (4.11 g, 20 mmol) in CH2Cl2 (10 mL) was slowly added over a period of 10 min at -20 oCSOCl2 (2.85 g, 24 mmol, 1.8 mL). The stirring was continued at -10 C until the reaction mixturebecame almost transparent. At this moment, a solution of 2-aminobenzophenone (3.94 g, 20 mmol)in CH2Cl2 (10 mL) was added to the reaction mixture at -30 C and 5 min later, NEt3 (6.6 mL) was thenintroduced. The stirring was continued at room temperature for 20 hours. After adding 10% aqueousNa2CO3 (30 mL) to the reaction mixture at 0 C, the organic layer was separated and the aqueouslayer extracted with CH2Cl2 (2 × 50 mL). The organic phases were combined, dried over Na2SO4,filtered and concentrated under reduced pressure. The crude residue obtained was purified bycolumn chromatography on silica gel using cyclohexane/EtOAc 95:5 as eluent to afford 11 (5.72 g,14.9 mmol, 77%) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | To a round bottomed flask containing dry DCM (475 mL) under N2 was added 7 (34.5 g, 143 mmol, 1 equiv.) to form a cloudy suspension. The reaction mixture was cooled to -20 C using a mixture of ice and NaCl (1:3), giving (on average) an internal temperature of -5 C. N-Methyl imidazole (31.8 mL, 399 mmol, 2.8 equiv.) was then added and stirred for 5 min. Methanesulfonyl chloride (12.2 mL, 157 mmol, 1.1 equiv.) was then added slowly over 5 min, maintaining the internal temperature at between -5 C to 0 C. The reaction mixture was then left to stir at -5 C-0 C for 30 min 2-Aminobenzophenone (25.3 g, 128 mmol, 0.9 equiv.) was then added and the reaction mixture left to stir at room temperature for 17 h. The reaction mixture was quenched with sat. NH4Cl and separated with DCM (3 400 mL). The organic layers were combined, dried and concentrated in vacuo to give the crude as a dark brown oil. The crude was then purified by silica chromatography (0-100% EtOAc in Pet. Ether 40/60) to give the title compound as a yellow solid (42.3 g, 86%). numax (neat): 3248, 2968, 2839, 2810, 1687, 1643, 1576, 1510, 1442 cm-1. 1H NMR (400 MHz, CDCl3): delta 11.54 (s, 1H), 8.59 (dd, 1H, J = 7.6, 1.2 Hz), 7.82-7.80 (m, 2H), 7.67-7.61 (m, 1H), 7.57-7.45 (m, 4H), 7.41-7.39 (m, 2H), 7.18-7.15 (m, 3H), 7.13-7.09 (m, 1H), 3.95 (d, 1H, J = 13.2 Hz), 3.62 (d, 1H, J = 13.2 Hz), 3.37 (dd, 1H, J = 5.2, 4.8 Hz), 3.27-3.22 (m, 1H), 2.47-2.40 (m, 1H), 2.33-2.23 (m, 1H), 2.03-1.96 (m, 1H), 1.90-1.76 (m, 2H). 13C NMR (101 MHz, CDCl3): delta 197.5, 174.1, 138.7, 138.1, 137.7, 132.9, 132.1, 132.0, 129.6, 128.7, 127.8, 127.7, 126.6, 124.9, 121.7, 121.1, 67.8, 59.4, 53.4, 30.5, 23.7. HRMS: (C25H25O2N2) [M+H]+ requires 385.1911, found [M+H]+ 385.1908. [alpha]D20 = -106.7 (c = 1, MeOH). ee = >98% by chiral HPLC, retention time = 11.95 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 13 (20 53 g, 0 10 mol) in CH2CI2 (150 mL) was added SOCI2 (9 0 mL, 0 125 mol) with stir?ng at -2O0C for 10mm The stirring was continued at -10C for 30miotan Then 2- amino benzophenone (13 80 g, 007 mol) was added to the reaction mixture at -300C and the stirring was continued at RT for additional 10 h The reaction mixture was neutralized with Na2CO3 at 0 C until pH 8-9 The organic layer was separated and the aqueous layer was extracted with CH2CI2 (50 mL*2) The combined organic layers were washed with brine, dried and evaporated The residue was purified by column chromatography (eluting with petroleum ether and EtOAc =30 1) on silica gel to give the product as a light yellow solid (17 4 g, 76 % for two steps) 1H NMR (300 MHz, DMSO-d6) delta 11 02 (s, 1 H), 825-8 28 (d, 1 H, J= 84 Hz), 745-7 75 (m, 7H), 7 10-7 31 (m, 6H), 3 72-3 76 (d, 1 H, J= 129 Hz), 3 50-3 54 (d, 1 H, J= 12 9 Hz), 3 14-3 18 (m, 1H), 2 94-2 99 (m, 1H), 2 07-2 18 (m, 1H), 2 30-238 (m, 1 H), 1 57- 1 72 (m, 3H) LC-MS 385 (M + H)+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With trifluoroacetic acid; at 100℃; for 0.5h; | General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 60℃; for 24h;Inert atmosphere; | To a mixture of 2-aminobenzophenone (1.1mmol, 0.22g) and 2-phenyl-2,3-dihydroquinolin-4-one (1.1mmol, 0.25g) was added T3P® (2.2mmol, 0.70g) and the reaction mixture stirred at 60°C for 24h. Water (100mL) was added to dissolve T3P® and the mixture extracted with dichloromethane (3×60mL). The combined organic extracts were washed with brine, dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was recrystallized from methanol to give product 6a as yellow needles (57percent). Mp 113?115°C. 1H NMR (400MHz, DMSO-d6) delta 8.38 (dd, J=7.9, 1.6Hz, 1H), 8.10 (dd, J=8.5, 1.2Hz, 1H), 7.74 (ddd, J=8.4, 6.8, 1.4Hz, 1H), 7.63 (m, 1H), 7.54?7.35 (m, 3H), 7.31 (t, J=7.6Hz, 1H), 7.25 (d, J=8.5Hz, 1H), 7.19?7.03 (m, 4H), 6.97 (d, J=2.7Hz, 1H), 6.83 (dt, J=5.9, 3.5Hz, 2H), 6.76?6.65 (m, 3H), 5.41 (d, J=2.6Hz, 1H). 13C NMR (151MHz, DMSO) delta 168.6, 151.3, 149.9, 147.1, 144.8, 137.1, 135.0, 131.6, 131.5, 129.9, 129.4, 128.9, 128.8, 128.6, 128.3, 128.1, 127.3, 127.1, 126.6, 126.1, 125.8, 125.1, 123.7, 120.5, 120.0, 117.3, 115.2, 54.9. IR (ATR): numax 3585, 3263, 2928, 2815, 2210, 1901, 1807, 1717, 1604, 1573, 1489cm?1. UV?VIS: lambdamax 389nm (epsilon 12447cm?1M?1). HRMS (C28H21N2) calcd m/z 385.1699 [M+H]+, obsd m/z 385.1695 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | General procedure: To a stirred solution of BOC/Fmoc amino acid (1a-1u) (1.5 mmol) in THF (15 mL) at 20 C, NMM (2.25 mmol) and ethyl chloroformate (1.5 mmol) were added and the reaction mixture was stirred at 20 C for 15 min. Later, to this 2-aminobenzophenone (1.5 mmol), NMM (2.25 mmol) were added and stirred at rt for 1-12h. The THF was removed in vacuo and the reaction mixture was diluted with ethyl acetate (30 mL) and washed with brine (30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product (with BOC/Fmoc) was used in the next step without further purification. |
Tags: 2-Aminobenzophenone | 2-Benzoylaniline | Amines | Aryls | Ketones | Organic Building Blocks | 2835-77-0
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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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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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P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
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. |
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P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
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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. |
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P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
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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. |
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P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
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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 | |
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Disposal | |
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Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
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H242 | Heating may cause a fire |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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Health hazards | |
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H305 | May be harmful if swallowed and enters airways |
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H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
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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 |
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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