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[ CAS No. 13380-67-1 ] {[proInfo.proName]}

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Chemical Structure| 13380-67-1
Chemical Structure| 13380-67-1
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Product Details of [ 13380-67-1 ]

CAS No. :13380-67-1 MDL No. :MFCD00030664
Formula : C10H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FECSFBYOMHWJQG-UHFFFAOYSA-N
M.W : 252.06 Pubchem ID :123301
Synonyms :

Safety of [ 13380-67-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13380-67-1 ]

* 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.

  • Downstream synthetic route of [ 13380-67-1 ]

[ 13380-67-1 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 123972-87-2 ]
  • [ 13380-67-1 ]
  • [ 134939-31-4 ]
  • 2
  • [ 13380-67-1 ]
  • 2,5-diphenyl-3-trimethylsilylmethyl-1,3,4-thiadiazolium trifluoromethanesulfonate [ No CAS ]
  • 2,7a-diphenyl-5,6,7,7a-tetrahydropyrrolo[2,1-b][1,3,4]thiadiazole-endo-6,7-N-(p-bromophenyl)dicarboxyimide [ No CAS ]
  • 3
  • [ 59256-47-2 ]
  • [ 13380-67-1 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic anhydride; for 2h;Reflux; General procedure: The synthesis of maleimides 1-47 was performed by mixing an equimolar amount of the appropriate maleic anhydrides 68-72 in 5 mL of CHCl3 and anilines 73, 78-90, amines 91-94 or phenylalkylamines 74-77 (5 mmol) dissolved in 1 mL of CHCl3 and stirred during 1 h. The solid (maleamic acid) which precipitated out of the reaction mixture was filtered off. The whole amount of maleamic acid was dissolved in 5 mL of acetic anhydride and 100 mg of sodium acetate was added. The mixture was heated for 2 h under reflux. The reaction was cooled and quenched with water; then, the aqueous solution was extracted with Et2O, dried with Na2SO4, filtered, and the solvent was evaporated. The product was purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (9:1) as eluent. Compounds 1-10, 16-26, 31-34, 36, 38-42 and 43-47 were previously reported.[3], [8], [21], [22], [23], [24], [25], [26], [27] and [28]
With sulfuric acid; acetic acid; at 60℃; for 0.75h; General procedure: Maleic anhydride (1.1 eq) was added at once with vigorous stirring in the solution of aniline (1.0 eq)in acetic acid (15 mL). It was stirred for another 10 minute while the reaction mixture turned into a suspension.To this reaction mixture concentrated sulphuric acid (2.0eq) was added at once while stirring. The temperature increased by 10oC and suspension turned into a clear solution. The temperature of reaction mixture was increased to 60oC and stirred furtherfor 45 minutes. It was allowed to come at room temperature and poured onto crushed ice. Thesolid separated was filtered and washed with water. The solid was transferred to the aqueous solution of sodium bicarbonate and stirred for 10 minutes to remove maleanilic acid if present. Then filtered and washed with water and recrystallized in ethanol. Yield: quantitative.
With sodium acetate; acetic anhydride; at 80℃; for 0.5h; General procedure: The maleamic acid was allowed to cyclodehydrated by using acetic anhydride and fused sodium acetate. The solution was stirred for 0.5 h at 80 C. The prepared produced is precipitated in ice, filtered and washed by water. The product was then crystallized by ethanol [6] (Fig. 1).
  • 4
  • [ 542-92-7 ]
  • [ 13380-67-1 ]
  • [ 72657-50-2 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 0.05h; General procedure: A mixture of the diene (1 mmol) and the dienophile (1 mmol)was subjected to hand grinding with a pestle and mortar for thetime shown in Tables 1 and 2 to afford the corresponding productsin quantitative yield. In the reactions of cyclopentadiene,1.2 equiv of the diene was used. In most cases, product formationwas observed by the change in color; with aryl maleimides,the yellow color of the initial reaction mixture changed to white, whereas with 1,3-diphenyl-2-benzofuran, the color of the mixture changed almost immediately from fluorescentgreen to white. 2-(4-Bromophenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3-dione (7b)White solid; yield: 317 mg (quant); mp 156 C. 1H NMR (500MHz, CDCl3): δ = 7.55 (dt, J = 2.5, 9.0 Hz, 2 H), 7.04 (dt, J = 2.5,9.5 Hz, 2 H), 6.25 (t, J = 1.5 Hz, 2 H), 3.53-3.47 (m, 2 H), 3.43 (q,J = 1.5 Hz, 2 H), 1.79 (d, J = 9.0 Hz, 1 H), 1.61 (d, J = 9.0 Hz, 1 H).13C NMR (125 MHz, CDCl3): δ = 176.3, 134.5, 132.1, 130.7, 128.1,122.2, 52.1, 45.7, 45.4.
  • 5
  • C-(4-methoxybenzyl)-N-phenylnitrone [ No CAS ]
  • [ 13380-67-1 ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
31.3%; 40.1% In benzene; at 40℃; A mixture of C-(4-methoxybenzyl)-N-phenylnitrone (0.300 g, 1.32 mmol), <strong>[13380-67-1]N-(4-bromophenyl)maleimide</strong> (0.333 g, 1.32 mmol) and benzene (2.6 μL) was stirred overnight at 40 C. The resultant suspension was cooled to room temperature and diluted with methylene chloride until a homogeneous mixture was achieved. The mixture was chromatographed (silica gel, 20% ethyl acetate/hexanes). 5-(4-Bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted first and was isolated as a tan solid (0.254 g, 40.1%): mp 203-205 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.50 (d, 4H), 7.32 (d, 2H), 7.20 (d, 2H), 7.04 (m, 3H), 6.60 (d, 2H), 5.75 (s, 1H), 5.15 (d, 1H), 4.06 (d, 1H), 3.86 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. 5-(4-Bromophenyl)-3-(4methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted second and was isolated as a tan solid (0.198 g, 31.3% yield): mp 206-208 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 2H), 7.39 (d, 2H), 7.25 (d, 2H), 7.15 (d, 3H), 7.03 (d, 2H), 6.90 (d, 2H), 5.30 (d, 1H), 4.90 (d, 1H), 4.08 (t, 1H), 3.78 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. Illustrative compound 113 is formed by mixing 115 and 117 to form a 1:1 mixture
  • 6
  • [ 3585-93-1 ]
  • [ 13380-67-1 ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
  • 5-(4-bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
31.3%; 40.1% In benzene; at 40℃; A mixture of C-(4-methoxybenzyl)-N-phenylnitrone (0.300 g, 1.32 mmol), <strong>[13380-67-1]N-(4-bromophenyl)maleimide</strong> (0.333 g, 1.32 mmol) and benzene (2.6 mL) was stirred overnight at 40 C. The resultant suspension was cooled to room temperature and diluted with methylene chloride until a homogeneous mixture was achieved. The mixture was chromatographed (silica gel, 20% ethyl acetate/hexanes). 5-(4-Bromophenyl)-3-(4-methoxyphenyl)-2-phenyl-trans-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted first and was isolated as a tan solid (0.254 g, 40.1%): mp 203-205 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.50 (d, 4H), 7.32 (d, 2H), 7.20 (d, 2H), 7.04 (m, 3H), 6.60 (d, 2H), 5.75 (s, 1H), 5.15 (d, 1H), 4.06 (d, 1H), 3.86 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+. 5-(4-Bromophenyl)-3-(4methoxyphenyl)-2-phenyl-cis-3-cis-3a-tetrahydropyrrolo[3,4-d]isoxazole-4,6-dione eluted second and was isolated as a tan solid (0.198 g, 31.3% yield): mp 206-208 C. dec; 1H NMR (300 MHz, CDCl3) δ 7.61 (d, 2H), 7.39 (d, 2H), 7.25 (d, 2H), 7.15 (d, 3H), 7.03 (d, 2H), 6.90 (d, 2H), 5.30 (d, 1H), 4.90 (d, 1H), 4.08 (t, 1H), 3.78 (s, 3H); APCI MS m/z 481 [C24H19BrN2O4+H]+.
  • 7
  • [ 90-44-8 ]
  • [ 13380-67-1 ]
  • (R,R)-(-)-4-hydroxy-2-(4-bromophenyl)-3a,4,9,9a-tetrahydro-4,9-[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-dione [ No CAS ]
  • [ 1041480-19-6 ]
YieldReaction ConditionsOperation in experiment
With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
With (1R,2R)-N,N-dimethyl-N'-phthaloyl-1,2-diaminocyclohexane; In 1,2-dichloro-ethane; at -10℃; for 12h; General procedure: A mixture of maleimide 3 (0.24 mmol), anthrone 2 (0.2 mmol), and the catalyst (20 mol %) in 1,2-dichloroethane (0.6 mL) at -10 C was stirred for 12 h (monitored by TLC). After evaporation under reduced pressure, the residue was purified through column chromatography on silica gel (petroleum ether/ethyl acetate=3/1) to yield pure products.
  • 8
  • [ 1158818-80-4 ]
  • [ 13380-67-1 ]
  • C24H21BrN2O6S [ No CAS ]
  • 9
  • [ 108-31-6 ]
  • [ 106-40-1 ]
  • [ 13380-67-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In glacial acetic acid; at 60℃; General procedure: To a solution of the substituted anilines (0.01 mol) in acetic acid (10 mL), the maleic anhydride was added. The reaction mixture was stirred for 10 min. To this suspension, sulfuric acid (0.025 mol) was added while stirring. The temperature of the reaction mixture was then maintained at 60 C for 30-45 min. The cooled reaction mixture was poured onto crushed ice. The solid separated was collected, washed with aqueous sodium bicarbonate and then with water, and recrystallized from aqueous ethanol [64].
With manganese(II) acetate; acetic anhydride; triethylamine; In acetone; at 50 - 60℃; for 3h; The maleic anhydride and para-bromoaniline are dissolved in a certain amount of acetone solvent,The reaction solution was added dropwise to a reaction flask containing a maleic anhydride solution with stirring,Reaction exotherm and gradually produce light yellow precipitate, room temperature reaction 1 hour,Take a small amount of precipitation, washed,Dry, followed by adding manganese acetate,Triethylamine and acetic anhydride,After warming, the precipitate gradually dissolves,The reaction was carried out at 50 to 60 C for 2 hours,Solution from orange to red and black, the gradual emergence of new precipitation,Cooled to room temperature, the water precipitated by a large number of washed,Dried and recrystallized from acetone to give the product N-p-bromophenylmaleimide (3).
General procedure: 5 mmol of maleic anhydride was put into to 50mL three-necked round-bottom flask and dissolved in 10 mL of diethyl ether upon stirring. The flask was equipped with a dropping funnel and reflux condenser. Then, 5 mmol of the given aniline was dissolved in 3mL diethyl ether and added to the flask through the dropping funnel.The reaction mixture was stirred at room temperature for 1 h. Next,the reaction mixture was cooled to the room temperature, was filtered off and washed with diethyl ether to separate N-substituted maleic acid. Afterward, the dried product added to the flask and mixed with anhydrous sodium acetate (0.16 g, 2 mmol) and acetic anhydride (2 mL) then stirred for 1 h at 80 C. The reaction mixture was cooled to the room temperature and poured into an ice-water mixture. The product washed with 20 mL of ice-cold water 3 times.The dried crude was recrystallized from n-hexane or n-hexane/acetone to obtain the corresponding product.
With glacial acetic acid; for 6h;Reflux; General procedure: The maleimides needed for the photocatalytic annulation reactions were prepared using the reported procedure [1]. To a stirred solution of maleic anhydride (25 mmol) in acetic acid (15 mL) was added the amine (10 mmol). The reaction mixture was stirred at reflux for 6 h, and then the acetic acid was removed in vacuum. The residue was dissolved in CH2Cl2 (20 mL) and washed with aqueous NaHCO3 (2 × 30 mL), HCl (1 M, 2 × 30 mL), and saturated aqueous NaCl (30 mL). The organic layer was separated, dried over Na2SO4, and the solvent was removed in vacuum. Purification by flash chromatography afforded the desired maleimide substrates

  • 10
  • N-((tributylstannyl)methyl)-N-(6-(trimethylsilyl)hex-4-enyl)formamide [ No CAS ]
  • [ 13380-67-1 ]
  • 2-(4-bromophenyl)-9-vinyloctahydro-1H-pyrrolo[3,4-a]indolizine-1,3(2H)-dione [ No CAS ]
  • 11
  • [ 1143-38-0 ]
  • [ 13380-67-1 ]
  • [ 1242103-50-9 ]
YieldReaction ConditionsOperation in experiment
91% With 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea; In toluene; at 20℃; for 14h; General procedure: To a stirred solution of catalyst (R,R)-V (10 mg, 0.025 mmol) in toluene (1 mL) were added the maleimide (0.30 mmol) and the anthrone (1a or 1b, 0.25 mmol). The reaction mixture was vigorously stirred at room temperature during 14 h, and the crude product was directly purified by column chromatography on silica gel (hexane/ethyl acetate mixtures) to afford the Diels-Alder or the Michael adduct. Racemic products were obtained from the corresponding substrates by catalysis with DABCO in toluene at room temperature.
  • 12
  • [ 563-80-4 ]
  • [ 13380-67-1 ]
  • [ 1233703-87-1 ]
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