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[ CAS No. 62281-07-6 ] {[proInfo.proName]}

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Chemical Structure| 62281-07-6
Chemical Structure| 62281-07-6
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Product Details of [ 62281-07-6 ]

CAS No. :62281-07-6 MDL No. :MFCD26407439
Formula : C24H51N Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 353.67 Pubchem ID :-
Synonyms :

Safety of [ 62281-07-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:2735
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 62281-07-6 ]

* 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 [ 62281-07-6 ]

[ 62281-07-6 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 62281-07-6 ]
  • [ 118129-60-5 ]
  • N,N-bis(2-decyl-1-tetradecyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxylic acid bisimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In water; butan-1-ol at 80℃; for 17h;
81% In water; butan-1-ol at 80℃; for 17h; Inert atmosphere; 1 1,7-bisbromo-3,4,9,10-tetracarboxylic dianhydride (2.74 g, 4.98 mmol) in 200 ml BuOH/H2O (1:1) was sonicated for 10 min, 2-decyl-1-tetradecylamine (6.2 g, 17.53 mmol) was added, and the reaction mixture was heated at 80° C. for 17 h under nitrogen. 20 ml HCl was added and the mixture stirred at room temperature for 30 min. The mixture was extracted with chloroform, dried over MgSO4, and filtered. The solvent was removed and the residue purified by chromatography eluting with 1:1 CHCl3/Hexane, 4.9 g (81%) red solid was obtained. 1H NMR (500 MHz, CDCl3): δ (ppm): 9.43 (d, J=8.5 Hz, 2H), 8.87 (s, 2H), 8.64 (d, J=8.0 Hz, 2H), 4.11 (d, J=7.0 Hz, 4H), 1.98 (m, 2H), 1.5-1.1 (m, 80H), 0.84 (m, 12H). 13C NMR (125 MHz, CDCl3): δ(ppm): 163.2, 162.7, 138.1, 132.9, 132.7, 130.0, 129.2, 128.4, 126.9, 123.1, 122.7, 120.8, 44.8, 36.6, 31.9, 31.7, 31.6, 30.0, 29.68, 29.65, 29.3, 26.5, 22.7, 14.1. (12 aliphatic carbons not observed presumably due to overlapping resonances). MS (MALDI), m/z: calculated for C72H105Br2N2O4 (M+H), 1219.6536; found 1220.6513. Elemental analysis, calc. for C72H104Br2N2O4, C, 70.80; H, 8.58; N, 2.29; found C, 70.98; H, 8.59; N, 2.34.
With acetic acid
  • 2
  • [ 62281-07-6 ]
  • [ 299962-88-2 ]
  • [ 1219501-16-2 ]
YieldReaction ConditionsOperation in experiment
19% Stage #1: 2-decyl-1-tetradecylamine; 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic dianhydride With acetic acid Reflux; Stage #2: With phosphorus tribromide In toluene Reflux;
19% Stage #1: 2-decyl-1-tetradecylamine; 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic dianhydride With acetic acid at 120℃; for 0.5 - 1h; Inert atmosphere; Stage #2: With phosphorus tribromide In toluene for 1h; Reflux; Synthesis of N,N'-di(2-decyltetradecyl)-2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic acid diimide (22): TBNDA (3.3 g, 5.7 mmol) and 2-decyl-tetradecyl amine (6.5 g, 18.4 mmol) were added into acetic acid (50 mL) under nitrogen atmosphere, heated to 120°C. Heating was terminated when the reaction liquid turned clear and before the color got dark (the heating lasted for about 0.5∼1 hour). After cooled to room temperature, the reaction solution was poured into water (400 mL) and filtered. The resulting precipitate was washed with water (200 mL), and dried under vacuum to obtain a yellow solid. The yellow solid and phosphorus tribromide (2.0 mL, 21.1 mmol) were added into anhydrous toluene (120 mL) and heated to reflux for 1 hour. After cooled to room temperature, the reaction liquid was poured into water (400 mL) and extracted with toluene (200 mL × 3). The organic phases were combined and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography column using dichloromethane/petroleum ether (1/2) as an eluent to give 1.35 g of a yellow solid (22), and the yield was 19% (calculated based on TBNDA as a starting material). MS (MALDI-TOF) m/z 1257.6 (M+); 1H-NMR (300 MHz, CDCl3) δ (ppm): 0.852-0.894 (m, 6H, -CH3), 1.287-1.409 (m, 8H, CH2), 1.235 (b, 40H, CH2), 1.970-2.005 (m, 1H, CH), 4.159-4.184 (d, J = 7.50 Hz, 2H, -CH2-N); 13C-NMR (100 MHz, CDCl3): δ 14.10, 22.67, 26.25, 29.33, 29.56, 29.64, 30.01, 31.50, 31.90, 36.50, 46.60, 125.75, 126.32, 135.23, 160.18 (CO).
19% In acetic acid at 120℃; Inert atmosphere; TBNDA (3.3 g, 5.7 mmol) and 2-decyl-tetradecyl amine (6.5 g, 18.4 mmol) were added into acetic acid (50 mL) under nitrogen atmosphere, heated to 120° C. Heating was terminated when the reaction liquid turned clear and before the color got dark (the heating lasted for about 0.51 hour). After cooled to room temperature, the reaction solution was poured into water (400 mL) and filtered. The resulting precipitate was washed with water (200 mL), and dried under vacuum to obtain a yellow solid. The yellow solid and phosphorus tribromide (2.0 mL, 21.1 mmol) were added into anhydrous toluene (120 mL) and heated to reflux for 1 hour. After cooled to room temperature, the reaction liquid was poured into water (400 mL) and extracted with toluene (200 mL×3). The organic phases were combined and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel chromatography column using dichloromethane/petroleum ether (1/2) as an eluent to give 1.35 g of a yellow solid (22), and the yield was 19% (calculated based on TBNDA as a starting material).MS (MALDI-TOF) m/z 1257.6 (M+);1H-NMR (300 MHz, CDCl3) δ (ppm): 0.852-0.894 (m, 6H, -CH3), 1.287-1.409 (m, 8H, CH2), 1.235 (b, 40H, CH2), 1.970-2.005 (m, 1H, CH), 4.159-4.184 (d, J=7.50 Hz, 2H, -CH2-N);13C-NMR (100 MHz, CDCl3): δ 14.10, 22.67, 26.25, 29.33, 29.56, 29.64, 30.01, 31.50, 31.90, 36.50, 46.60, 125.75, 126.32, 135.23, 160.18 (CO).
  • 3
  • [ 62281-07-6 ]
  • [ 113377-10-9 ]
  • [ 4885-93-2 ]
  • [ 299962-88-2 ]
  • [ 1351161-74-4 ]
YieldReaction ConditionsOperation in experiment
21% Stage #1: 2-(2,4-dithia-1,5-disodapentan-3-ylidene)propanedinitrile; 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic dianhydride In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: 2-decyl-1-tetradecylamine; N-(2-aminoethyl)tricosa-10,12-diynamide In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;
  • 4
  • [ 62281-07-6 ]
  • [ 1122-12-9 ]
  • [ 1301741-17-2 ]
  • 7
  • [ 62281-07-6 ]
  • [ 25121-83-9 ]
  • C30H53NS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
15.5% With potassium phosphate; copper(l) iodide; copper at 80℃; for 48h; 1 Preparation of compound 5a Compound 6a (5.00 g, 22.82 mmol, 1 equiv.), copper (0.07 g, 1.14 mmol, 5 mol%) copper(l)iodide (0.22 g, 1.14 mmol, 5 mol%), potassium phosphate tribasic (9.69g, 45.64 mmol, 2 equiv.)and 2-decyltetradecyl amine (12.11 g, 34.23 mmol, 1.5 equiv.) were heated with stirring in dimethyl aminoethanol (50 mL) at 80 °C for 48 hours. Upon cooling to room temperature, water and hexane were added. The aqueous layer was extracted several times with hexanes. The organic layers were combined, dried over MgSO4 and the solvent was removed by rotary evaporation. The crude product was passed through a small silica column using hexane as solvent to affordcompound 5a as brown oil (1.74 g, 3.54 mmol, 15.5 %). 1H NMR (400 MHz, CDCI3); 67.36 (dd, J= 5.3, 1.4 Hz, 1H), 6.05 (d, 1H, J= 2.1 Hz), 3.56 (s, 1H), 3.13 (d, J= 6.1 Hz, 2H), 1.29 (bm, 40H), 0.91 (m, 6H).
With dipotassium hydrogenphosphate; copper(l) iodide; 3-aminobutan-2-ol; copper at 80℃;
  • 8
  • [ 62281-07-6 ]
  • [ 6007-85-8 ]
  • 5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% Thieno[3,4-c]furan-1,3-dione (3.0 g, 0.0194 mol) anddecyltetradecan-1-amine (7.5 g, 0.021 mol) were addedinto toluene (300 mL) and refluxed for 24 h at 100 C. Andthen the solvent was removed, thionyl chloride (300 mL)was added, and the mixture was stirred for an additional4 h at 80 C. The mixture was then cooled down to roomtemperature, and the solvent was removed. Further purificationwas carried out by applying column chromatographyon silica gel using n-hexane:dichloromethane (1:1).Yield: 7.05 g (74%). 1H NMR (300 MHz, CDCl3: 7.81
  • 9
  • [ 62281-07-6 ]
  • [ 293738-03-1 ]
  • 5-bromo-N-(2-decyltetradecyl)-2-iodobenzene [ No CAS ]
  • 10
  • [ 62281-07-6 ]
  • [ 1015423-45-6 ]
  • 1,3-dibromo-5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]
  • 11
  • [ 58670-89-6 ]
  • [ 62281-07-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; triphenylphosphine / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 18 h / 90 °C / Inert atmosphere 3: hydrazine hydrate / methanol / 12 h / 95 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: pyridine / 0.5 h / 0 °C 1.2: 2 h 2.1: N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 3.1: hydrazine / methanol / 12 h / 95 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere 1.2: 16 h 2.1: N,N-dimethyl-formamide / 16 h / Reflux 3.1: hydrazine hydrate / water; methanol / 16 h / Reflux
Multi-step reaction with 3 steps 1: triphenylphosphine; bromine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 90 °C / Inert atmosphere 3: hydrazine hydrate / methanol / 45 h / 95 °C

  • 12
  • [ 62281-07-6 ]
  • [ 6007-85-8 ]
  • 1,3-dibromo-5-(2-decyltetradecyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.98% 2 mmol of <strong>[6007-85-8]3,4-thiophenedicarboxylic anhydride</strong> and 2.6 mmol of 2-decyl-1-tetradecylamine were added to a refluxing reactor equipped with a stirrer, 15 mL of toluene solvent was added, pass nitrogen protection, at 120 C under the conditions, Reflux 24h; The reaction was cooled to room temperature, And 16 mmol of dibromo sulfoxide was added under stirring at 0 C, Then 18 mmol of anhydrous pyridine was added, This mixture was stirred at room temperature for 5 hours, Heated to 120 C reflux reaction for 24h, the end of the reaction, the reaction cooled to room temperature, And then the product slowly dumped in a beaker containing ice, stirring constantly, The organic layer was collected by extraction with dichloromethane, and the organic layer was dried over anhydrous magnesium sulfate, filtered, evaporated, and subjected to column chromatography, rotary distillation, suction filtration and vacuum drying to obtain a compound of the formula of product yield was 89.98%.
  • 13
  • [ 62281-07-6 ]
  • [ 1542-34-3 ]
  • [ 4885-93-2 ]
  • [ 299962-88-2 ]
  • C52H51F2IN6O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% Under ambient conditions, a solution of 3 (500 mg, 0.86 mmol) and sodium 1,1-dicyanoethene-2,2-dithiolate (480 mg, 2.57 mmol) in DMF (25 mL) was stirred at 55 C for 1 hour. Then 2-decyltetradecylamine (394 mg, 1.11 mmol) and 3,5-difluoroiodoaniline[2] (371 mg, 1.46 mmol) were added to the reaction mixture. The resulting purple black solution was stirred at 55 C for 12 hours, and water (200 mL) was added to quench the reaction. The product was extracted with CH2Cl2 (3 × 50 mL), and the combined organic solution was washed with water, brine, and dried over anhydrous MgSO4. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography with CH2Cl2 as eluent. Compound 1 was obtained as a purple red solid (yield: 10 %).
  • 14
  • [ 62281-07-6 ]
  • [ 372-39-4 ]
  • [ 4885-93-2 ]
  • [ 299962-88-2 ]
  • C52H52F2N6O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% Stage #1: 2-(2,4-dithia-1,5-disodapentan-3-ylidene)propanedinitrile; 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylic dianhydride In N,N-dimethyl-formamide at 55℃; for 1h; Stage #2: 2-decyl-1-tetradecylamine; 3,5-difluoroaniline In N,N-dimethyl-formamide at 55℃; for 12h; 2,2-[2-(3,5-difluoro-4-iodo)phenyl-8-(2-decyltetradecyl)-1,2,3,7,8,9-hexahydro-1,3,7,9-tetraoxo[1,3]benzodithiolo[4,5,6,7-lmn][1,3]dithiolo[4,5-f][3,8]phenanthroline-5,11-diylidine]bis(malononitrile) (1). General procedure: Under ambient conditions, a solution of 3 (500 mg, 0.86 mmol) and sodium 1,1-dicyanoethene-2,2-dithiolate (480 mg, 2.57 mmol) in DMF (25 mL) was stirred at 55 °C for 1 hour. Then 2-decyltetradecylamine (394 mg, 1.11 mmol) and 3,5-difluoroiodoaniline[2] (371 mg, 1.46 mmol) were added to the reaction mixture. The resulting purple black solution was stirred at 55 °C for 12 hours, and water (200 mL) was added to quench the reaction. The product was extracted with CH2Cl2 (3 × 50 mL), and the combined organic solution was washed with water, brine, and dried over anhydrous MgSO4. After removing the solvent under reduced pressure, the crude product was purified by silica gel column chromatography with CH2Cl2 as eluent. Compound 1 was obtained as a purple red solid (yield: 10 %).
  • 15
  • [ 62281-07-6 ]
  • [ 86-90-8 ]
  • 5-bromo-2-(2-decyltetradecyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetic acid; at 120℃; for 8h; General procedure: To a mixture of <strong>[86-90-8]4-bromo-phthalic anhydride</strong> (1.5 g, 6.61 mmol) and2-butyl-octylamine (1.41 g, 7.60 mmol), 10 mL of acetic acid was addedas a solvent and stirred at 120 C for 8 h. When the reaction was determinedto be complete, the reaction was cooled to room temperature,and then extracted with chloroform and water. The organic layer wasdried with anhydrous Na2SO4 and concentrated by vacuum evaporationto obtain colourless oil. The crude product was purified by silica gelchromatography using a mixture of hexane and DCM as eluent to obtainproduct as colourless oil (2.0 g, 75%).
  • 16
  • [ 62281-07-6 ]
  • [ 19725-82-7 ]
  • 7-bromo-2-(2-decyltetradecyl)isoquinolinedione [ No CAS ]
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