[ CAS No. 189178-09-4 ] {[proInfo.proName]}

Name: 189178-09-4|Tris(4-ethynylphenyl)amine|98%
Brand: Ambeed
SKU: A693154
Price: 26.0 USD
Availability: InStock
Rating: 99 (22 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 189178-09-4 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 189178-09-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 189178-09-4 ]

SDS Specification

Alternatived Products of [ 189178-09-4 ]

Product Details of [ 189178-09-4 ]

CAS No. :	189178-09-4	MDL No. :	MFCD09030768
Formula :	C₂₄H₁₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QGICIDGCKPUALM-UHFFFAOYSA-N
M.W :	317.38	Pubchem ID :	23443705
Synonyms :

Safety of [ 189178-09-4 ]

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 [ 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 1~88

1
[ 827-15-6 ]
[ 189178-09-4 ]
tris-4,4',4''-(pentafluorophenylethynyl)triphenylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146

2
[ 619-44-3 ]
[ 189178-09-4 ]
[ 848568-96-7 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146

3
[ 79887-18-6 ]
[ 189178-09-4 ]
(4-ethynylphenyl)amine]-co-[(4-heptyloxy)phenylacetylene], hyperbranched, M_w: 18200, polydispersity index: 5.3, temperature for 5 percent loss: 456 deg C; monomer(s): tris(4-ethynylphenyl)amine; (4-heptyloxy)phenylacetylene [ No CAS ]

Reference： [1]Journal of Physical Chemistry B,2004,vol. 108,p. 10645 - 10650

4
[ 19524-06-2 ]
[ 189178-09-4 ]
[ 359647-66-8 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146

5
[ 189178-08-3 ]
[ 189178-09-4 ]

Yield	Reaction Conditions	Operation 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.

Reference： [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, M_w: 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 ]

Reference： [1]Journal of Physical Chemistry B,2004,vol. 108,p. 10645 - 10650

7
[ 92874-17-4 ]
[ 189178-09-4 ]
4,4',4''-tri(N-butyl-4-ethynyl)-1,8-naphthalimide-triphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Molecular Crystals and Liquid Crystals,2017,vol. 645,p. 1 - 9
[2]Chemistry Letters,2005,vol. 34,p. 922 - 923

8
4-azido-N,N-dihexylbenzenamine [ No CAS ]
[ 189178-09-4 ]
C₇₈H₁₀₅N₁₃ [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 2029 - 2031

9
[ 4181-20-8 ]
[ 1066-54-2 ]
[ 189178-09-4 ]

Reference： [1]Journal of Fluorescence,2014,vol. 24,p. 197 - 202
[2]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 370,p. 207 - 210
[3]Dyes and Pigments,2016,vol. 124,p. 101 - 109

10
[ 189178-09-4 ]
polymer; monomer(s): tris(4-ethynylphenyl)amine [ No CAS ]

Reference： [1]Macromolecules,2004,vol. 37,p. 5196 - 5210

11
[ 4316-58-9 ]
mono(6percent) and dibromo TBPA(2percent) [ No CAS ]
[ 189178-09-4 ]

Reference： [1]Dalton Transactions,2006,p. 3693 - 3698

12
[ 4181-20-8 ]
[ 189178-09-4 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146
[2]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736
[3]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 1830 - 1839
[4]Chemistry - A European Journal,2012,vol. 18,p. 12487 - 12497
[5]Chemical Communications,2013,vol. 49,p. 780 - 782
[6]Chemistry - An Asian Journal,2013,vol. 8,p. 2984 - 3001
[7]Angewandte Chemie - International Edition,2015,vol. 54,p. 12748 - 12752
Angew. Chem.,2015,vol. 127,p. 12939 - 12943,4
[8]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355
[9]Journal of Materials Chemistry C,2016,vol. 4,p. 2535 - 2544
[10]Molecular Crystals and Liquid Crystals,2017,vol. 645,p. 1 - 9
[11]Chemical Communications,2017,vol. 53,p. 8778 - 8781
[12]RSC Advances,2017,vol. 7,p. 47681 - 47688

13
[ 189178-09-4 ]
tris-4,4',4''-(4-carboxyphenylethynyl)triphenylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146

14
[ 189178-09-4 ]
tris-4,4',4''-[N-(4-methyl)-4-pyridinioethynyl]triphenylamine trisiodide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 1134 - 1146

15
cis-[RuCl₂(dppe)2] [ No CAS ]
[ 189178-09-4 ]
(tri(4-ethynylphenyl)amine(-3H))[Ru(dppe)2Cl]3 [ No CAS ]

Reference： [1]Dalton Transactions,2006,p. 3693 - 3698

16
[ 15636-79-0 ]
[ 189178-09-4 ]
[ 1007866-62-7 ]

Reference： [1]Organometallics,2008,vol. 27,p. 316 - 319
[2]Organometallics,2009,vol. 28,p. 4288 - 4296

17
[ 177595-61-8 ]
[ 189178-09-4 ]
tris-[4-(4-dimesitylborylphenylethynyl)phenyl]amine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 198 - 208

18
[ 51458-06-1 ]
[ 189178-09-4 ]
[ 1127353-49-4 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 198 - 208

19
[ 53694-87-4 ]
[ 189178-09-4 ]
[ 943154-17-4 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: US2009/221819,2009,A1 .Location in patent: Page/Page column 13; 14

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 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: US2009/221819,2009,A1 .Location in patent: Page/Page column 13

21
3,5-bis((E)-2-phenylethenyl)-8-(4-iodophenyl)-4,4'-difluoroboroadiazaindacene [ No CAS ]
[ 189178-09-4 ]
C₁₁₇H₇₈B₃F₆N₇ [ No CAS ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Patent: US2009/221819,2009,A1 .Location in patent: Page/Page column 14

22
[ 368455-15-6 ]
[ 189178-09-4 ]
[ 1173285-12-5 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9186 - 9188

23
[ 1207158-64-2 ]
[ 189178-09-4 ]
[ 1207158-63-1 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 521 - 524

24
[ 259145-15-8 ]
[ 189178-09-4 ]
[ 1207158-62-0 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 521 - 524

25
[ 609770-35-6 ]
[ 189178-09-4 ]
[ 1267583-47-0 ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 2226 - 2232

26
[ 654070-00-5 ]
[ 189178-09-4 ]
[ 1338574-43-8 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736

27
[ 1123-99-5 ]
[ 189178-09-4 ]
[ 1338574-48-3 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736

28
[ 1025452-30-5 ]
[ 189178-09-4 ]
[ 1338574-49-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736

29
[ 1338574-28-9 ]
[ 189178-09-4 ]
[ 1338574-44-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736

30
[ 603-34-9 ]
[ 189178-09-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8726 - 8736
[2]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 1830 - 1839
[3]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355
[4]Molecular Crystals and Liquid Crystals,2017,vol. 645,p. 1 - 9
[5]Chemical Communications,2017,vol. 53,p. 8778 - 8781
[6]RSC Advances,2017,vol. 7,p. 47681 - 47688
[7]Angewandte Chemie - International Edition,2021,vol. 60,p. 11326 - 11334
Angew. Chem.,2021,vol. 133,p. 11427 - 11435,9

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 ]

Reference： [1]European Journal of Inorganic Chemistry,2012,p. 65 - 75

32
4,4',4''-(4,40',4''-nitrilotris(benzene-4,1-diyl))tris(2-methylbut-3-yn-2-ol) [ No CAS ]
[ 189178-09-4 ]

Reference： [1]European Journal of Inorganic Chemistry,2012,p. 65 - 75
[2]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 1830 - 1839

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 ]

Reference： [1]Dyes and Pigments,2012,vol. 94,p. 28 - 33

34
[ 15636-79-0 ]
[ 189178-09-4 ]
[ 1007866-64-9 ]

Reference： [1]Organometallics,2008,vol. 27,p. 316 - 319

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 ]

Reference： [1]Organometallics,2012,vol. 31,p. 1635 - 1642

36
[ 934-71-4 ]
[ 189178-09-4 ]
[ 1421132-91-3 ]