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CAS No. : | 3958-60-9 |
Formula : | C7H6BrNO2 |
M.W : | 216.03 |
SMILES Code : | C1=CC=CC(=C1CBr)[N+](=O)[O-] |
MDL No. : | MFCD00007184 |
InChI Key : | HXBMIQJOSHZCFX-UHFFFAOYSA-N |
Pubchem ID : | 77569 |
GHS Pictogram: | ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H302+H312+H332-H314-H290 |
Precautionary Statements: | P501-P260-P270-P234-P271-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P406-P405 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.1 |
TPSA ? Topological Polar Surface Area: Calculated from | 45.82 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.51 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 2.68 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 2.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.69 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 0.67 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.78 |
Log S (ESOL):? ESOL: Topological method implemented from | -3.14 |
Solubility | 0.157 mg/ml ; 0.000725 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (Ali)? Ali: Topological method implemented from | -3.29 |
Solubility | 0.11 mg/ml ; 0.000508 mol/l |
Class? Solubility class: Log S scale | Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -3.04 |
Solubility | 0.196 mg/ml ; 0.000908 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -5.71 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 3.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.91 |
* 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 |
---|---|---|
40% | Compound 42 (200 mg, 1.33 mmol) was dissolved in DMF (9.0 mL) and cooled to 0 0C with ice bath. To this solution under nitrogen were added in sequence NaH (60percent in mineral oil, 133 mg, 3.33 mmol) and l-(bromomethyl)-2-nitrobenzene (432 mg, 2.00 mmol). The reaction mixture was stirred for 1 h then treated with 1.0 M HCl (10.0 mL). After extraction with ethyl acetate, the organic phase was washed with water and saturated brine. After rotary evaporation, the residue was purified by column chromatography over silica gel to give the title compound (153 mg, 40percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.17 (s, IH), 8.15 (d, J = 7.2 Hz, IH), 7.83- 7.76 (m, 2H), 7.66-7.59 (m, IH), 7.37-7.30 (m, 2H), 7.15 (dd, J = 8.1 2.4 Hz, IH), 5.48 (s, 2H) and 4.92 (s, 2H) ppm; Mp: 135-138 0C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With tetrabutylammomium bromide; potassium hydroxide; In methanol; at 50℃; for 2h;Large scale; | (1) Condensation: 1 Add 1500 kg of methanol, 362 kg of potassium hydroxide and 10 kg of tetrabutylammonium bromide to the reaction vessel, start stirring, and increase the temperature to 50°C and then add 300 kg of 1-(4-chlorophenyl)-3- pyrazoleol, and 900kg of o-nitrobenzylbromide was added dropwise, and the reaction was carried out at 50°C for 2 hours, followed by cooling down to 15°C and centrifugation to obtain 450kg of the centrifuged solid as a crude condensate; 2). After adding 450kg of crude condensate to 500kg of methanol, wash it and cool it to 15°C filter, Filter cake at -0.08 Mpa, 60 °C drying 10 hours to give 360 kg condensation product, a purity of 98.5percent, a yield of 96.5percent; |
70% | In dimethyl sulfoxide; at 25℃; for 1h; | Using the same flask as used in the preparation of 1-(4-chlorophenyl)-3- hydroxy-1H-pyrazole, a dropping funnel filled with 2-nitrobenzyl bromide of formula (IV) was connected. The ratio of 2-nitrobenzyl bromide to the <strong>[76205-19-1]1-(4-chlorophenyl)-3-hydroxy-1H-pyrazole</strong> present in the flask 1.7: 1 While being kept at a temperature of 25°C, the solution of 2-nitrobenzyl bromide was dropped into the flask at a rate of 0.5 ml/minute. After all of the 2-nitrobenzyl bromide was added to the flask, the reaction was mixed for 1 hour, until all of the <strong>[76205-19-1]1-(4-chlorophenyl)-3-hydroxy-1H-pyrazole</strong> was consumed. A small amount of NaOH 15percent was then added to the solution and the solution was then stirred for 30 minutes at 30°C. A small amount of H2O was added to the mixture in order to precipitate the crude product. The crude product was recrystallized using MCB. The product was dried in a vacuum oven at 25 mbar at 70°C. Yield of 1-(4-chlorophenyl)-3-[(2-nitrophenyl)methoxy]-1H-pyrazole: 70percent with a purity of 99.1percent. |
With sodium hydroxide; In water; at 48℃; for 1.6h; | First of all, to the condensation kettle containing o-nitrobenzyl bromobenzene solution into the solid1- (4-chlorophenyl) -3-pyrazole alcohol, wherein 1- (4-chlorophenyl) -3-pyrazole alcohol andNitrobenzyl bromide molar ratio of 1: 1.7; then heated to 48 ° C dropwise aqueous sodium hydroxide solution,The concentration of sodium hydroxide aqueous solution is 20percent; and then after the completion of the dropwise addition to cool to room temperature,And then incubated 1.6h crystallized, centrifuged; and then into the centrifuge after the solid was refined into refined kettle; and then into the above refining kettle methanol was heated to 49 ° C reflux 5 hours;Then then the aforementioned refining kettle material was cooled to room temperature, and then incubated 1.8h crystallization,Centrifuged; Finally, the centrifuged solid was dried to obtain pure product2 - [(N-4-chlorophenyl) -1H-pyrazol-3-yloxymethyl] nitrobenzene.Which before adding the catalyst and DMF in the condensation reactor before heating, pass into the oxygen,The temperature was raised to 50 dropping sodium hydroxide solution, the reaction time was 20h. |
362 kg | With 1-bromo-butane; sodium hydroxide; at 80 - 82℃; for 2h;pH >= 13;Green chemistry; Large scale; | In the second step, in the 5m3 reactor, the initial raw material is 350 kg of p-chloroaniline, which is subjected to salt formation, diazotization, acidification, extraction, cyclization and oxidation.After the reaction of 1-(4-chlorophenyl)pyrazol-3-one to 1-(4-chlorophenyl)-3-pyrazolol,When 1-(4-chlorophenyl)pyrazol-3-one <2percent, liquid chromatography analysis at this time:P-chlorophenylhydrazine hydrochloride: 1.562percent;1-(4-chlorophenyl)pyrazol-3-one: 0.687percent;1-(4-Chlorophenyl)-3-pyrazolol: 95.832percent; high boiler (aldehyde): 1.919percent.All the o-nitrobenzyl bromide prepared in the above batch is put into the 1-(4-chlorophenyl)-3-pyrazolol solution, and an appropriate amount of sodium hydroxide solution is added to adjust the pH to 13 or more;Then, 0.2 kg of 4-butyl bromide catalyst with a purity of 99percent was added to the reaction vessel, and the temperature was raised to 80 ° C to 82 ° C, and the temperature was kept for 2 hours.Liquid chromatography analysis of 1-(4-chlorophenyl)-3-pyrazol <1percent was acceptable, stood still for 1 hour, layered, and cooled to 3 °C. In the third step, the lower layer was centrifuged and dried in a dryer to obtain 362 kg of 2-{(N-4-chlorophenyl)-3-pyrazoloxymethyl}nitrobenzene.Chromatographic purity:p-Chlorobenzoquinone hydrochloride: 0.315percent; 1-(4-chlorophenyl)pyrazol-3-one 0.112percent; o-nitrobenzyl bromide: 0.124percent,1-(4-Chlorophenyl)-3-pyrazol: 0.673percent; 2-{(N-4-chlorophenyl)-3-pyrazoloxymethyl}nitrobenzene:98.124percent. High boiler (aldehyde): 0.652percent. |
With potassium carbonate; In acetone; for 3h;Reflux; | 1-(4-chlorophenyl)-3-pyrazol,Acetone and potassium carbonate are added to the reaction flask,After heating to reflux, a solution of o-nitrobenzyl bromide in acetone is added dropwise.After the completion of the dropwise addition, the reflux reaction is carried out for at least 3 hours.The acetone was concentrated and removed, and then methanol was refluxed for at least 20 min, cooled to room temperature, allowed to stand for at least 30 min, and filtered.Obtaining 2-[(N-p-chlorophenyl)-3-pyrazoloxymethyl]nitrobenzene for use; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.3% | With tetrabutylammomium bromide; potassium hydroxide; at 80 - 85℃; for 1.5h; | In a stirrer,thermometer,Reflux condenser and dropping funnel in a four-neck reaction flask,Add 19.5g (0.1piomicron1)3-hydroxy-ox- (p-chlorophenyl) pyrazole alcohol,5percent potassium hydroxide 134 g (0.12 mol) and 0.5 gTetrabutylammonium bromide, the reactants were heated to 80 ° C,At this temperature,Add o-nitrobenzyl bromide23.7 g (0.1 lmol),Dropping time is about 0.5h,Drop finished,Continue stirring at 80-85 ° C for 1.5 h.After cooling, the reaction is cooled to below 5 ° C,filter,The filter cake was washed with ethanol,Dried to give 30.4 g of a white solid,Yield 92.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Potassium carbonate (1.38 g, 10.0 mmol) was added to a solution of ascorbyl palmitate (4.15 g, 10.0 mmol) in 40 ml of 1 : 1 THF/DMSO. The resultant mixture was allowed to stir for 30 min. A solution of 2-nitrobenzyl bromide in 20 mL of 1 : 1 THF/DMSO was then added dropwise via addition funnel over 10 min. The resultant mixture was allowed to stir under nitrogen atmosphere for 70 hours, during which time it became dark orange in color. Approximately 200 mL of H2O was added to the mixture, which was then extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated to an orange oil. This material was purified via suction filter chromatography (S1O2, ramp eluent from 5: 1 to 3 : 1 hexane/EtOAc) to afford 2.27 g of product as a light tan solid (41% yield). MR was consistent with the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22%; 3% | An oven-dried, 250-mL RB flask was cooled under nitrogen. The flask was charged with a stir bar, L-ascorbic acid-6-palmitate (9.53 g, 23.0 mmol), and the potassium carbonate (3.18 g, 23.0 mmol). The flask was then purged with nitrogen, after which time 60 mL THF and 60 mL DMSO were added. The mixture was stirred for 10 minutes at room temperature under nitrogen. The flask was purged again with nitrogen, after which time 2-nitrobenzyl bromide (4.97 g, 23.0 mmol) was added. This mixture was purged with nitrogen for 10 minutes, and allowed to stir at room temperature under nitrogen (flask wrapped in foil) for 5 days. Next, 120 mL sat. aq. NaCl was added to the mixture, followed by 100 mL ethyl acetate. The resulting mixture was shaken and separated, and the aqueous layer extracted with two further portions of 120 mL ethyl acetate. The resulting organic layer was washed with 3x150 mL water, dried over MgS04, filtered, and concentrated under reduced pressure to a red oil. This oil, when cooled, solidified into a dark red/brown solid that did not liquefy upon returning to room temperature. NMR of this crude material in d6-DMSO showed there to be some impurities. Trituration of the crude material in hexanes followed by filtering appeared to remove some palmitic acid and leave behind a purer but still not clean material. Thin layer chromatography showed the primary product (RF = 0.16) with a less-polar impurity (RF = 0.50) in a 2: 1 hexanes/EtOAc medium. These conditions were used to formulate a method on a BIOTAGE ISOLERA ONE automatic chromatography machine (Biotage USA, Charlotte, NC). Biotage columns were run on the crude material. Isolation of the RF = 0.50 fraction showed it to be the diprotected product (NB2AscPalm). The isolated yield of the diprotected product was 0.520 g (3% yield). Isolation of the RF = 0.16 fraction showed it to be the monoprotected product shown above (PE-6). The isolated yield of the monoprotected product (NBAscPalm, PE-6) was 2.79 g (22% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.13 g | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; | To a solution of l-(tert-butyl) 3-methyl 3-hydroxypyrrolidine-l,3-dicarboxylate (Intermediate C, 0.7 g, 2.857 mmol) in DMF (10 ml) were added K2C03(1.18 g, 8.571 mmol) and 2-nitrobenzyl bromide (CAS Number 3958-60-9; 0.74 g, 3.428 mmol) at rt. The reaction mixture was stirred at rt for 16 h then poured into water (150 ml) and extracted with EtOAc (3 x 100 ml). The combined organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (neutral aluminium oxide, 5% EtOAc in hexane) yielding l-(tert-butyl) 3-methyl 3-((2-nitrobenzyl)oxy)pyrrolidine-l,3- dicarboxylate (0.13 g, 0.342 mmol). LCMS: Method 1, 2.557 min, MS: ES+ 325.5 (M-56); 1H NMR (400 MHz, DMSO-d6) delta ppm: 8.04 (d, J=8.0 Hz, 1 H), 7.76 (d, J=4.0 Hz, 2 H), 7.57 - 7.60 (m, 1 H), 4.78 - 4.91 (m, 2 H), 3.71 (s, 3 H), 3.58 - 3.61 (m, 2 H), 3.41 - 3.48 (m, 1 H), 3.33 - 3.35 (m, 1 H), 2.26 - 2.28 (m, 2 H), 1.38 (d, J=13.6 Hz, 9 H). |
Tags: 3958-60-9 synthesis path| 3958-60-9 SDS| 3958-60-9 COA| 3958-60-9 purity| 3958-60-9 application| 3958-60-9 NMR| 3958-60-9 COA| 3958-60-9 structure
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
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P103 | Read label before use |
Prevention | |
Code | Phrase |
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Code | Phrase |
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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. |
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P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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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. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
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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