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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.
3-Bromopropan-1-ol is a halogenated alcohol compound, commonly used in organic synthesis for the preparation of brominated intermediates.
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CAS No. : | 627-18-9 |
Formula : | C3H7BrO |
M.W : | 138.99 |
SMILES Code : | OCCCBr |
MDL No. : | MFCD00002942 |
InChI Key : | RQFUZUMFPRMVDX-UHFFFAOYSA-N |
Pubchem ID : | 12308 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H227-H302-H318 |
Precautionary Statements: | P210-P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P370+P378-P403+P235-P501 |
* 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 |
---|---|---|
80% | With potassium carbonate In acetonitrile at 95℃; for 4 h; | Intermediate 121: tert-Butyl 4-(3-hvdroxypropyr)piperazine-l -carboxylate A mixture of tert-butyl piperazine-1 -carboxylate (2.75 g, 14.8 mmol), l-bromo-3- propanol (1.43 mL, 16.2 mmol) and potassium carbonate (2.25 mL, 27.5 mmol) in acetonitrile (75 mL) was heated at 950C for 4 hours. The solvent was removed under reduced pressure, and the residue was taken up in dichloromethane (300 mL) and washed with water, brine, EPO <DP n="118"/>dried over sodium sulfate and concentrated under reduced pressure. Chromatography on silica gel with methanol in dichloromethane (0-10percent) gave a tan solid 2.88 g (80percent yield). MS (ESV 245 (MH+) for C12H24N2O3,1H-NMR TCDCl1) δ: 1.44 (m, 9H); 1.70-1.82 (m, 2H); 2.40-2.53 (m, 2H); 2.62-2.65 (m, 2H); 3.43-3.50 (m, 4H); 2.77 (m, 2H); 3.73-3.82 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; for 15h; | Potassium carbonate (269 g) and pyrrolidine (200 mL) were added in that order to a THF solution (500 mL) of 3-bromopropanol (200 g) at 0°C. The reaction liquid was stirred at room temperature for 15 hours, then ethyl acetate (500 mL) was added to it, and further stirred at room temperature for 1 hour. The obtained reaction liquid was filtered through Celite, and the solid on the Celite was washed with ethyl acetate. The wash liquid and the filtrate were concentrated under reduced pressure, and ethyl acetate (500 mL) was added to the resulting residue, then stirred for 1 hour and filtered through Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified through distillation (boiling point: 62°C, 1 mmHg) to obtain (3-hydroxypropyl)pyrrolidine (156 g, yield 95 percent). 1HNMR (400 MHz, CDCl3, delta ppm): 1.69-1.78 (6H, m), 2.53-2.59 (4H, m), 2.73 (2H, t, J=5.6 Hz), 3.81 1 (2H, t, J=5.4 Hz), 5.58 (1H, brs) |
86.3% | To a solution of pyrrolidine (1.5 g, 19.5 mmol) in toluene (10 rnL) was added 3- bromopropanol (5.4 g, 39.0 mmol) and and the reaction mixture heated at 8O0C for 5.5 hrs. After cooling to RT, the toluene was evaporated at reduced pressure and the residue partitioned between DCM (25 mL) and aqueous K2CO3 (25 mL). The organic layer was collected and the aqueous phase extracted with DCM (4 x 25 mL). The combined organic layers were evaporated at reduced pressure to provide the title compound (1.2 g, 86.3 percent) as brown oil.1H NMR (500 MHz, MeOD) delta ppm 3.61 (2 H, t, J=6.3 Hz), 2.48 - 2.71 (6 H, m), 1.70 - 1.89 (6 H, m). | |
70% | With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; for 15h; | Potassium carbonate (1.4 g, 0.94 mol) and pyrrolidine(0.87 mL, 1.8 mol) were added to a stirred solution of 3-bromopropanol (1 g, 0.635 mol) in30 mL of THF at 0 °C, and the resulting mixture was stirred at room temperature for 15 h.The resulting mixture was diluted with ethyl acetate (200 mL) and filtered through celite.The filtrate was concentrated, and the residue was subjected to column chromatography(silica gel), eluting with 50percent methanol in dichloromethane, to yield a yellow oil (0.57 g,70percent). 1HNMR (300 MHz, CDC13) 3.79 (t, J = 5.1 Hz, 2 H), 2.71 (t, J= 5.6 Hz, 2 H), 2.57-2.51 (m, 4 H), 1.75-1.66 (m, 6 H); ?3C NMR (125 MHz, CDC13) 64.18, 56.02, 54.09,29.24, 23.27. |
69% | With potassium carbonate; In tetrahydrofuran; at 0 - 20℃; | Preparation of Compound 48,53-(pyrrolidin-1-yl)propan-1-ol[0068] Pyrrolidine (1 .00 ml_, 12.0 mmol) was added to a suspension of potassium carbonate (1 .29 g, 9.35 mmol) and 3-bromopropanol (0.65 ml_, 7.2 mmol) in dry THF (3 mL) at 0 °C. The reaction mixture was then allowed to warm to rt, stirred overnight, diluted with EtOAc, filtered through a silica pad and the filtrate concentrated to afford the title compound (645 mg, 69percent) as a colourless oil.1H NMR (500 MHz, CDCl3) delta 5.54 (br s, 1 H), 3.84 - 3.77 (m, 2H), 2.77 - 2.68 (m, 2H), 2.60 - 2.53 (m, 4H), 1 .80 - 1 .68 (m, 6H). LRMS (ESI+) (M + H)+: 130.12 |
59% | In toluene; at 20℃; for 48h; | 3-Bromopropan-1-ol (27.3mL, 302mmol) was added to a solution of pyrrolidine (47.2g, 655mmol) in toluene (1000mL) and the mixture was stirred at room temperature for 48 hours. The reaction mixture was then filtered and the filtrate was evaporated under reduced pressure. The residue was distilled and the title product was obtained as a colourless liquid at 100°C/7mmHg, (23.1g, 59percent). 1H-NMR(CDCl3, 400MHz) delta: 1.60-1.82(m, 6H), 2.50-2.60(m, 4H), 2.75(m, 2H), 3.80(m, 2H) MS ES+ m/z 130 [MH]+ |
With potassium carbonate; In acetonitrile;Heating / reflux; | A suspension of pyrrolidine (8.35 ml), 3-bromo-1-propanol (8.67 ml), and potassium carbonate (17.28 g) in MeCN (100 ml) was heated under reflux overnight. The reaction mixture was filtered and evaporated in vacuo. The residue was partitioned between EtOAc (100 ml) and 1 M HCl (50 ml). The organic layer was separated and extracted with 1 M HCl (2 x 25 ml). The combined acidic extract was adjusted to pH 13 with solid KOH, while cooling in ice/H2O. The resulting clear, slightly yellowish solution was extracted with DCM (5 x 50 ml). The combined organic extract was dried over Na2SO4 and evaporated in vacuo. The crude product was purified by vacuum distillation employing a 5 cm Vigreux column at a pressure of ca. 15 mbar (with an oil-bath temperature of ca. 120 °C). The fraction distilling off at 89-90 °C was collected. The product was obtained as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; In acetonitrile; | EXAMPLE 7 Preparation of 4-[3-(4-fluorobiphenyl-4'-oxy)propoxy]-1,3-diaminobenzene (20) STR13 Using 2.8 g (14.9 mmol) of 4-fluoro-4'-hydroxybiphenyl, 50 ml of acetonitrile, 2.17 g (15.6 mmol) of 3-bromopropanol and 4.11 g (30 mmol) of anhydrous potassium carbonate, synthetic treatment was carried out in the same manner as in Example 2. The obtained colorless powder was recrystallized from benzene/n-hexane to obtain 3.26 g (yield: 89%) of 4-fluoro-4'-(3-hydroxypropoxy)biphenyl (18) as a colorless powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; | <strong>[42017-89-0]Fenofibric acid</strong> is esterified with 3-bromopropanol (n=l) in the presence of dicyclohexylcarbodiimide (DCC) and 4-dimethylamino pyridine (DMAP). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | To a suspension solution of <strong>[391-78-6]6-fluoroquinolin-4-ol</strong> (3.67 g, 22.5 mmol) (synthesized in overall yield of 32percent starting from 4-fluoroaniline and diethyl ethoxymethylenemalonate according to a literature procedure (see Price et al., Organic Syntheses, Coll. Vol. 3, p. 272; Vol. 28, p. 38), triphenylphosphine (6.56 g, 25 mmol), and 3-bromo-1-propanol (2.3 mL, 25 mmol) in dry tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (4.9 mL, 25 mmol) at 25° C. over 30 minutes under nitrogen and the reaction mixture was left stirring for one hour. Hydrobromic acid (2.8 mL of 48percent aqueous solution, 25 mmol) was added, resulting in precipitation of the titled compound. The product was collected by suction filtration and washed with THF, acetone and ether to give a light yellow crystalline solid (4.17 g, 51percent). 1H NMR (400 MHz, DMSO-d6): 2.45 (2H, m), 3.82 (2H, t, J=6.5 Hz), 4.61 (2H, t, J=5.7 Hz), 7.64 (1H, d, J=6.6 Hz), 8.40 (1H, dt, J=8.5, 2.7 Hz), 7.90 (m, 1H), 8.27 (1H, dd, J=9.4, 4.8 Hz), 9.24 (1H, d, J=6.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a suspension solution of <strong>[23432-43-1]6-chloroquinolin-4-ol</strong> (2.16 g, 12 mmol), triphenylphosphine (3.78 g, 14.4 mmol, 1.2 eq.), and 3-bromo-1-propanol (1.30 ml, 14.4 mmol, 1.2 eq.) in dry tetrahydrofuran (40 mL) was added diethyl azodicarboxylate (2.51 g, 14.4 mmol, 1.2 eq.) at 25 C. over 20 minutes under nitrogen and the reaction mixture was left stirring for an additional hour. Hydrobromic acid (1.36 mL, 12 mmol, 48% aqueous solution, 1.0 eq.) was added resulting in white solid as the corresponding hydrobromide salt. The white salt was filtered and digested with three times of diethyl ether. The white salt was neutralized by aqueous potassium carbonate solution and followed by extraction with dichloromethane. Upon evaporation of the dichloromethane layers gave the crude product which was subjected to purify by column chromatography (silica gel, 2% methanol in CH2Cl2 as eluent) to provide the bromo compound as white solid (2.52 g, 70%, m.p. 102-103.5 C. (dec.)). 1H NMR (500 MHz, CDCl3): 2.50 (2H, m), 3.70 (2H, t, J=6.3 Hz), 4.36 (2H, t, J=5.8 Hz), 6.79 (1H, d, J=5.3 Hz), 7.64 (1H, dd, J=9.0, 2.4 Hz), 7.99 (1H, d, J=9.0 Hz), 8.14 (1H, d, J=2.4 Hz), 8.75 (1H, d, J=5.2 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 90℃; for 5h; | A solution of 2-piperazin-1 -yl-1 ,3-benzoxazole (0.48 g, 2,4 mmol), 3- bromo-1 -propanol (0.36 g, 2.6 mmol, 1 .1 eq.) and DIPEA (0.41 mL, 2.4 mmol, 1 eq.) in MeCN (10 mL) was stirred at 90 ^ for 5 hours. After the mixture was allowed to cool down, water (10 mL) was added. The mixture was extracted with DCM (3X20 mL). The organic phases were combined and washed with water (2X5 mL), dried over MgS04 and concentrated under reduced pressure. The product was purified by flash silica chromatography (DCM : Methanol = 90 : 10) to afford [4-(1 ,3-benzoxazol-2-yl)piperazin-1 -yl]propan-1 -ol (0.47 g, 77 %). ESI-MS m/z: 262 ([M+H]+, 100%); RT= 0.95 min(Method 3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.6% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; | Intermediate 35 3-(3-(trifluoromethoxy)phenoxy)propan-l -ol To a solution of <strong>[827-99-6]3-(trifluoromethoxy)phenol</strong> (0.3 g, 1.68 mmol) in DMF (10 mL) was added 3- bromopropan-l-ol (0.47 g, 3.37 mmol) and potassium carbonate (0.47 g, 3.37 mmol). The reaction was heated at 80 C overnight. The mixture was cooled and partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether and ethyl acetate(10: l) to give 3-(3-(trifluoromethoxy)phenoxy)propan-l -ol (0.32 g, 80.6 % yield) as yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 18-crown-6 ether; potassium carbonate; In [(2)H6]acetone; for 24h;Inert atmosphere; Reflux; | 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone (3.0 g, 15.3 mmol), 18-crown-6 (0.0606 g, 0.229 mmol) and potassium carbonate (2.74 g, 19.9 mmol) were taken in a two neck round bottom flask equipped with a stir bar. The flask was vacuumed and refilled with N2 three times. Acetone (30 mL) was added through syringe and needle. The mixture was stirred at room temperature for 30 minutes, followed by addition of 1-bromo-3-propanol (1.6 mL, 18.3 mmol). The mixture was refluxed for 24 hours and then filtered. Acetone was removed under vacuum to yield the crude product (3.8 g) which was used in the next step without purification. Purification can be performed by column chromatography (30% ethyl acetate and 70% hexane) to get pure product (1.64 g): 1H NMR (300 MHz, DMSO-d6) delta ppm 1.76 (t, J=6.44 Hz, 2H) 2.55 (s, 3H) 3.54 (d, J=5.27 Hz, 2 H) 3.82 (s, 6 H) 4.01 (q, J=7.03 Hz, 2 H) 7.22 (s, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.70 g | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 17h; | 5-fluoro-picolinonitrile the (1.25g) was dissolved in dimethyl formamide (40mL).The reaction solution was cooled to 0 was added sodium hydride (0.39g).It was added to the reaction mixture of 3-bromo-propanol (1.0g).Then, the mixture was stirred at room temperature for 17 hours.The reaction mixture was purified by silica gel column chromatography, to give the title compound (0.70g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; | A solution of (S)-ieri-butyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate(Preparation 27) (200 mg, 0.592 mmol) in DMF (10 mL) was treated with Cs2C03 (386 mg, 1.18 mmol) and 3-bromopropanol (80 mu, 0.89 mmol), and the reaction mixture was stirred at room temperature. When TLC indicated the consumption of (S)-ieri-butyl 2-(tert-butoxycarbonylamino)-3-(4- hydroxyphenyl)propanoate, the reaction mixture was diluted with water and extracted with EtOAc (2 chi 30 mL). The combined organic layer was washed with brine, dried over Na2S04, filtered, and concentrated under reduced pressure to give the crude product. Purification by flash chromatography on silica gel with Hex:EtOAc (1 :2) afforded the title compound as a white solid (164 mg, 70%). Preparation 29: (S)-4-(3-tert-butoxy-2-(ieri-butoxycarbonylamino)-3-oxopropyl)phenyl 4-(5-allyl-6- methyl-2-phenylpyrimidin-4-ylamino)benzoate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 6h;Inert atmosphere; | General procedure: Phenyl esters 1a-1c (0.5 mmol) were loaded into a flask (10 mL). DMF (2 mL) and Cs2CO3 (488 mg,1.5 mmol, 3.0 equiv) were then added, which was followed by the addition of 3-bromoethanol (2a,0.525 mmol, 1.05 equiv). Then the reaction mixture was stirred at 80 C for 6 h under an Ar atmosphere. After completion of the reaction, as confirmed by TLC, the reaction mixture was cooled down to roomtemperature and 10 mL of CH2Cl2 (DCM) and 10 mL of water were added. After separation of thedichloromethane layer from the water, the aqueous phase was extracted with CH2Cl2 (2 5 mL) again.The combined organic layers were then dried over anhydrous Na2SO4, filtered, and concentratedunder vacuum to yield the crude product. The crude product was purified by silica gel columnchromatography to obtain the desired pure compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.3% | With potassium carbonate; In acetonitrile; at 20℃; for 5h; | To a solution of 3-methoxypyrrolidine (500 mg, 3.63 mmol, HCl) and 3-bromopropan-1-ol (505 mg, 3.63 mmol) in CH 3CN (10 mL) was added K 2CO 3 (1.51 g, 10.9 mmol). The mixture was stirred at 20° C. for 5 hours. The solid was filtered and the filtrate was evaporated to give 3-(3-methoxypyrrolidin-1-yl)propan-1-ol (540 mg, 3.39 mmol, 93.3% yield). |
Tags: 627-18-9 synthesis path| 627-18-9 SDS| 627-18-9 COA| 627-18-9 purity| 627-18-9 application| 627-18-9 NMR| 627-18-9 COA| 627-18-9 structure
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P410 | Protect from sunlight. |
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. |
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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