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Chemical Structure| 189178-09-4

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Product Details of [ 189178-09-4 ]

CAS No. :189178-09-4
Formula : C24H15N
M.W : 317.38
SMILES Code : C#CC1=CC=C(N(C2=CC=C(C#C)C=C2)C3=CC=C(C#C)C=C3)C=C1
MDL No. :MFCD09030768
InChI Key :QGICIDGCKPUALM-UHFFFAOYSA-N
Pubchem ID :23443705

Safety of [ 189178-09-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 189178-09-4 ]

* 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 [ 189178-09-4 ]

[ 189178-09-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 827-15-6 ]
  • [ 189178-09-4 ]
  • tris-4,4',4''-(pentafluorophenylethynyl)triphenylamine [ No CAS ]
  • 2
  • [ 619-44-3 ]
  • [ 189178-09-4 ]
  • [ 848568-96-7 ]
  • 3
  • [ 79887-18-6 ]
  • [ 189178-09-4 ]
  • (4-ethynylphenyl)amine]-co-[(4-heptyloxy)phenylacetylene], hyperbranched, Mw: 18200, polydispersity index: 5.3, temperature for 5 percent loss: 456 deg C; monomer(s): tris(4-ethynylphenyl)amine; (4-heptyloxy)phenylacetylene [ No CAS ]
  • 4
  • [ 19524-06-2 ]
  • [ 189178-09-4 ]
  • [ 359647-66-8 ]
  • 5
  • [ 189178-08-3 ]
  • [ 189178-09-4 ]
YieldReaction ConditionsOperation in experiment
87% With water; sodium hydroxide; In tetrahydrofuran; at 20℃; for 18h; In reference to FIG. 2, a third compound according to the present invention, arbitrarily called CL64, was also synthesized, according to diagram 2 below, by a Sonogashira triple coupling between trialkyne 4b (obtained by deprotection of 4a in a basic medium) and 3.5 equivalents of the iodized derivative 5.More specifically, an aqueous solution of NaOH (1 M, 30 mL) is added to a solution of the compound 4a (2.33 g, 4.36 mmol) in THF (30 mL), and the mixture is agitated vigorously at 20 C. for 18 h. After evaporation of the THF, dichloromethane is added. The organic phase is separated, washed with water and dried (Na2SO4). The residue obtained after removal of the solvent is purified by chromatography on a silica column (heptane/CH2Cl2 90:10, then 85:15) to produce 1.20 g (87%) of the compound 4b.The air is purged with a solution of compound 4b (17.9 mg, 0.056 mmol), compound 5 (100 mg, 0.197 mmol) and tri-o-furylphosphine (0.52 mg, 2.26 μmol) in 1.5 mL of toluene/Et3N (5/1) by argon bubbling for 30 min. Then, Pd2 dba3 (0.26 mg, 0.28 μmol) is added, and the mixture is agitated at 20 C. for 20 h. After evaporation of the solvent under reduced pressure, the raw product is purified by chromatography on a silica column (heptane/CH2Cl2 60:40, then 50:50) to produce 19 mg (24%) of CL64.
References: [1]Journal of Materials Chemistry C,2020,vol. 8,p. 10774 - 10780.
[2]Dalton Transactions,2006,p. 3693 - 3698.
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 12748 - 12752.
    Angew. Chem.,2015,vol. 127,p. 12939 - 12943,4.
[4]Patent: US2009/221819,2009,A1 .Location in patent: Page/Page column 13.
[5]Chemistry - A European Journal,2012,vol. 18,p. 12487 - 12497.
[6]Chemistry - An Asian Journal,2013,vol. 8,p. 2984 - 3001.
[7]Angewandte Chemie - International Edition,2021,vol. 60,p. 11326 - 11334.
    Angew. Chem.,2021,vol. 133,p. 11427 - 11435,9.
[8]Molecules,2022,vol. 27.
[9]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146.
[10]Tetrahedron Letters,2010,vol. 51,p. 521 - 524.
[11]New Journal of Chemistry,2016,vol. 40,p. 10246 - 10258.
[12]Chemical Communications,2013,vol. 49,p. 780 - 782.
[13]Patent: EP1170273,2002,A1 .Location in patent: Page 8.
[14]Journal of the American Chemical Society,2021,vol. 143,p. 16284 - 16292.
[15]Macromolecules,2010,vol. 43,p. 7577 - 7582.
[16]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736.
[17]Journal of Photochemistry and Photobiology A: Chemistry,2014,vol. 290,p. 22 - 30.
[18]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355.
[19]Journal of Materials Chemistry C,2016,vol. 4,p. 2535 - 2544.
[20]Molecular Crystals and Liquid Crystals,2017,vol. 645,p. 1 - 9.
[21]Chemical Communications,2017,vol. 53,p. 8778 - 8781.
[22]RSC Advances,2017,vol. 7,p. 47681 - 47688.
[23]Green Chemistry,2019,vol. 21,p. 6606 - 6610.
  • 6
  • [ 189178-09-4 ]
  • poly[tris(4-ethynylphenyl)amine], hyperbranched, Mw: 24100, polydispersity index: 1.6, temperature for 5 percent loss: 516 deg C, weight residue at 900 deg C: 78.0 percent; monomer(s): tris(4-ethynylphenyl)amine [ No CAS ]
  • 7
  • [ 92874-17-4 ]
  • [ 189178-09-4 ]
  • 4,4',4''-tri(N-butyl-4-ethynyl)-1,8-naphthalimide-triphenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In flame dried Schlenk flask (100 mL), <strong>[189178-09-4]tris(4-ethynylphenyl)amine</strong> (105.8 mg, 0.33 mmol), Pd(PPh3)4 (62.4mg, 0.054 mol), CuI (3.4mg, 0.018mmol), and anhydrous THF (10 mL) were charged under N2 atmosphere. After 30 min stirring, 4-bromo-1,8-napthalimide (328.9 mg,0.99 mmol) in anhydrous THF (20 mL) and Et3N (6 mL) were added. The mixture was stirred at room temperature overnight. After the starting materials were full reacted, as confirmed by TLC, the mixture was poured to distilled water 50mL. Then, it was extracted by dichloromethane (25 mL × 3). The organic phase dried over Mg2SO4 and evaporated in vacuum. The residue was loaded to the column. Column separation (silica gel 200-300 mesh,eluent: dichloromethane/petroleum = 2/1) produced 286 mg yellow powder (80%).Mp: 281-284C; IR (KBr, υ, cm-1): 780, 1085, 1235, 1274, 1319, 1353, 1503, 1511, 1587,1660, 1697, 2196, 2960. 1H NMR(400 MHz, CDCl3): δ (ppm): 8.73 (3H, d, J = 8.0 Hz), 8.65(3H, d, J = 8.0 Hz), 8.56 (3H, d, J = 8.0 Hz), 7.95 (3H, d, J = 8.0 Hz), 7.84 (3H, t, J = 8.0Hz), 7.64 (6H, d, J = 8.0 Hz), 7.23 (6H, d, J = 8.0 Hz), 4.20 (6H, t, J = 8.0 Hz), 1.73 (6H, m), 1.53-1.44 (6H, m), 0.99 (9H, t, J = 8.0 Hz). 13C NMR (100 MHz, CDCl3): δ (ppm): 164.1,163.9, 147.4, 133.5, 132.4, 131.73, 131.67, 130.7, 130.5, 128.2, 127.7, 127.6, 124.5, 123.2, 122.2,118.1, 117.5, 99.1, 86.8, 40.5, 30.4, 29.8, 20.6, 14.0.Maldi-Tof: [M+H]+ C72H56N4O5 requires1071.412; found [M+H]+ 1071.501; and [M+2H]+ C72H57N4O5 requires 1072.420; found1072.508 (Base).
  • 8
  • 4-azido-N,N-dihexylbenzenamine [ No CAS ]
  • [ 189178-09-4 ]
  • C78H105N13 [ No CAS ]
  • 10
  • [ 189178-09-4 ]
  • polymer; monomer(s): tris(4-ethynylphenyl)amine [ No CAS ]
  • 11
  • [ 4316-58-9 ]
  • mono(6percent) and dibromo TBPA(2percent) [ No CAS ]
  • [ 189178-09-4 ]
  • 13
  • [ 189178-09-4 ]
  • tris-4,4',4''-(4-carboxyphenylethynyl)triphenylamine [ No CAS ]
  • 14
  • [ 189178-09-4 ]
  • tris-4,4',4''-[N-(4-methyl)-4-pyridinioethynyl]triphenylamine trisiodide [ No CAS ]
  • 15
  • cis-[RuCl2(dppe)2] [ No CAS ]
  • [ 189178-09-4 ]
  • (tri(4-ethynylphenyl)amine(-3H))[Ru(dppe)2Cl]3 [ No CAS ]
  • 16
  • [ 15636-79-0 ]
  • [ 189178-09-4 ]
  • [ 1007866-62-7 ]
  • 17
  • [ 177595-61-8 ]
  • [ 189178-09-4 ]
  • tris-[4-(4-dimesitylborylphenylethynyl)phenyl]amine [ No CAS ]
  • 18
  • [ 51458-06-1 ]
  • [ 189178-09-4 ]
  • [ 1127353-49-4 ]
  • 19
  • [ 53694-87-4 ]
  • [ 189178-09-4 ]
  • [ 943154-17-4 ]
YieldReaction ConditionsOperation in experiment
22% With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In toluene; at 20℃; for 20h;Inert atmosphere; Synthesis of 4-[(4-azidophenyl)ethynyl]-N,N-bis[4-[(4-azidophenyl)ethynyl]phenyl]-benzenamine (11) In reference to , this compound was synthesised, according to diagram 5 below. The air is purged from a solution of 4-ethynyl-N,N-bis(4-ethynylphenyl)benzenamine (4b), (64 mg, 0.202 mmol), 1-azido-4-iodo-benzene (10) (197.6 mg, 0.807 mmol) and tri-2-furylphosphine (2 mg, 8.6 micromol) in 6 mL of toluene/Et3N (5/1) by argon bubbling for 30 min. Then, tris(dibenzylideneacetone)-dipalladium (0) (11 mg, 12 micromol) is added and the mixture is agitated at 20 C. for 20 h. After evaporation of the solvent under reduced pressure, the raw product is purified by chromatography on a silica column (heptane/CH2Cl2 80:20) to produce 30 mg (22%) of 11.
  • 20
  • 2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene [ No CAS ]
  • [ 189178-09-4 ]
  • [ 943154-15-2 ]
YieldReaction ConditionsOperation in experiment
24% With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In toluene; at 20℃; for 20h;Inert atmosphere; In reference to FIG. 2, a third compound according to the present invention, arbitrarily called CL64, was also synthesized, according to diagram 2 below, by a Sonogashira triple coupling between trialkyne 4b (obtained by deprotection of 4a in a basic medium) and 3.5 equivalents of the iodized derivative 5.More specifically, an aqueous solution of NaOH (1 M, 30 mL) is added to a solution of the compound 4a (2.33 g, 4.36 mmol) in THF (30 mL), and the mixture is agitated vigorously at 20 C. for 18 h. After evaporation of the THF, dichloromethane is added. The organic phase is separated, washed with water and dried (Na2SO4). The residue obtained after removal of the solvent is purified by chromatography on a silica column (heptane/CH2Cl2 90:10, then 85:15) to produce 1.20 g (87%) of the compound 4b.The air is purged with a solution of compound 4b (17.9 mg, 0.056 mmol), compound 5 (100 mg, 0.197 mmol) and tri-o-furylphosphine (0.52 mg, 2.26 μmol) in 1.5 mL of toluene/Et3N (5/1) by argon bubbling for 30 min. Then, Pd2 dba3 (0.26 mg, 0.28 μmol) is added, and the mixture is agitated at 20 C. for 20 h. After evaporation of the solvent under reduced pressure, the raw product is purified by chromatography on a silica column (heptane/CH2Cl2 60:40, then 50:50) to produce 19 mg (24%) of CL64.
  • 21
  • 3,5-bis((E)-2-phenylethenyl)-8-(4-iodophenyl)-4,4'-difluoroboroadiazaindacene [ No CAS ]
  • [ 189178-09-4 ]
  • C117H78B3F6N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine;tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane; In toluene; at 20℃; for 15h;Inert atmosphere; In reference to FIG. 6, a seventh compound according to the present invention, arbitrarily called MC297, was synthesized according to diagram 6 below.The air is purged from a solution of 3,5-bis((E)-2-phenylethenyl)-8-(4-iodophenyl)-4,4'-difluoroboroadiazaindacene (17) (105 mg, 0.176 mmol), 4-ethynyl-N,N-bis(4-ethynylphenyl)-benzenamine (4b) (15.9 mg, 0.050 mmol) and tri-2-furylphosphine (0.5 mg, 2.15 micromol) in 2 mL of toluelle/Et3N (5/1) by argon bubbling for 20 min. Then, tris(dibenzylideneacetone)-dipalladium (0) (2.8 mg, 3.06 micromol) is added and the mixture is agitated at 20 C. for 15 h. After evaporation of the solvent under reduced pressure, the raw product is purified by chromatography on a silica column (heptane/CH2Cl2 70:30, 50/50 then pule CH2Cl2) to produce 50 mg (58%) of MC303.
  • 22
  • [ 368455-15-6 ]
  • [ 189178-09-4 ]
  • [ 1173285-12-5 ]
  • 23
  • [ 1207158-64-2 ]
  • [ 189178-09-4 ]
  • [ 1207158-63-1 ]
  • 24
  • [ 259145-15-8 ]
  • [ 189178-09-4 ]
  • [ 1207158-62-0 ]
  • 25
  • [ 609770-35-6 ]
  • [ 189178-09-4 ]
  • [ 1267583-47-0 ]
  • 26
  • [ 654070-00-5 ]
  • [ 189178-09-4 ]
  • [ 1338574-43-8 ]
  • 27
  • [ 1123-99-5 ]
  • [ 189178-09-4 ]
  • [ 1338574-48-3 ]
  • 28
  • [ 1025452-30-5 ]
  • [ 189178-09-4 ]
  • [ 1338574-49-4 ]
  • 29
  • [ 1338574-28-9 ]
  • [ 189178-09-4 ]
  • [ 1338574-44-9 ]
  • 31
  • sodium hexaflorophosphate [ No CAS ]
  • cis-[RuCl2(dppe)2] [ No CAS ]
  • [ 189178-09-4 ]
  • trans,trans,trans-[(Ru(CCH-4-C6H4)Cl(1,2-bis(diphenylphosphanyl)ethane)2)3N][PF6]3 [ No CAS ]
  • 32
  • 4,4',4''-(4,40',4''-nitrilotris(benzene-4,1-diyl))tris(2-methylbut-3-yn-2-ol) [ No CAS ]
  • [ 189178-09-4 ]
  • 33
  • [ 1360629-98-6 ]
  • [ 189178-09-4 ]
  • 3,3',3''-(4,4',4''-(4,4',4''-(4,4',4''-nitrilotris(benzene-4,1-diyl))-tris(1H-1,2,3-triazole-4,1-diyl))tris(2,5-bis(hexyloxy)benzene-4,1-diyl))tris(2-cyanoacrylic acid) [ No CAS ]
  • 34
  • [ 15636-79-0 ]
  • [ 189178-09-4 ]
  • [ 1007866-64-9 ]
  • 35
  • [ 17084-13-8 ]
  • (1,2,3,4,5-pentamethylcyclopentadienyl)(1,2-bis(diphenylphosphino)ethane)iron(II)Cl [ No CAS ]
  • [ 189178-09-4 ]
  • [((η2-dppe)(η5-C5Me5)Fe=C=CH-1,4-C6H4)3N][PF6]3 [ No CAS ]
 

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