[ CAS No. 79887-09-5 ] {[proInfo.proName]}

Name: 79887-09-5|4-Butylphenylacetylene|97%
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Quality Control of [ 79887-09-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 79887-09-5 ]

Product Details of [ 79887-09-5 ]

CAS No. :	79887-09-5	MDL No. :	MFCD00173885
Formula :	C₁₂H₁₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZVWWYEHVIRMJIE-UHFFFAOYSA-N
M.W :	158.24	Pubchem ID :	2775132
Synonyms :

Calculated chemistry of [ 79887-09-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	53.76
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.87
Log Po/w (XLOGP3) :	4.13
Log Po/w (WLOGP) :	3.09
Log Po/w (MLOGP) :	4.96
Log Po/w (SILICOS-IT) :	4.0
Consensus Log Po/w :	3.81

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.59
Solubility :	0.0402 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (Ali) :	-3.84
Solubility :	0.023 mg/ml ; 0.000146 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.07
Solubility :	0.0135 mg/ml ; 0.0000855 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.71

Safety of [ 79887-09-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 79887-09-5 ]

* 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.

Upstream synthesis route of [ 79887-09-5 ]
Downstream synthetic route of [ 79887-09-5 ]

[ 79887-09-5 ] Synthesis Path-Upstream 1~6

1
[ 202524-78-5 ]
[ 79887-09-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	at 20℃; for 4 h;	To a solution of Pd(OAc)2 (13.5 mg, 0.06mmol), PPh3 (31.5 mg, 0.12 mmol), CuI (5.7 mg, 0.03 mmol), and 1-bromo-4-butylbenzene (639 mg,3.00 mmol) in triethylamine (1 mL) was added a solution of trimethylsilylacetylene (324 mg, 3.30mmol). After the mixture was stirred at 80 oC for 4 h, the reaction mixture was acidified with 1NHCl aq. Water and EtOAc were added, and then the organic layer was separated. The aqueous layerwas extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4,filtered through a pad of Celite, and then evaporated under reduced pressure. The residual brown oilwas chromatographed on silica gel with hexane/EtOAc = 100/1 (Rf = 0.43) to give1-(4-butylphenyl)-2-trimethylsilylacetylene (S8) as pale-yellow oil (550 mg, 2.40 mmol, 80 percent). Theanalytical data were identical to the literature.S15 A suspension of S8 (550 mg, 2.40 mmol) andK2CO3 (495 mg, 3.58 mmol) in MeOH (12 mL) was stirred at room temperature for 4 h. Thereaction mixture was filtered through Celite with EtOAc, and the solvent of the filtrate was removedunder reduced pressure. Water and EtOAc were added, and then the organic layer was separated. Theaqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, driedover MgSO4, filtered through a pad of Celite, and then evaporated under reduced pressure. Theresidual yellow oil was chromatographed on silica gel with hexane/EtOAc = 50/1 (Rf = 0.50) to give1-butyl-4-ethynylbenzene (S9) as pale-yellow oil (340 mg, 2.15 mmol, 90percent). The analytical datawere identical to the literature.S16 To a solution of Pd(OAc)2 (8.8 mg, 0.039 mmol), PPh3 (20.5 mg,0.078 mmol), CuI (3.7 mg, 0.020 mmol), and S9 (416 mg, 1.95 mmol) in triethylamine (1 mL) wasadded a solution of 1-butyl-4-ethynylbenzene (340 mg, 2.15 mmol). After the mixture was stirred at80 oC for 4 h, the reaction mixture was acidified with 1N HCl aq. After the same work-up performedin the synthesis of S8, the residue was chromatographed on silica gel with hexane/EtOAc = 50/1 (Rf= 0.30) to give 4c as yellow solid (340 mg, 1.17 mmol, 60 percent). The analytical data were identical tothe literature.S17

Reference： [1] Bulletin of the Chemical Society of Japan, 2018, vol. 91, # 7, p. 1069 - 1074
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1440 - 1446

2
[ 155906-12-0 ]
[ 79887-09-5 ]

Reference： [1] Journal of Materials Chemistry, 2009, vol. 19, # 40, p. 7525 - 7531
[2] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 711 - 718

3
[ 41492-05-1 ]
[ 79887-09-5 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 711 - 718
[2] Bulletin of the Chemical Society of Japan, 2018, vol. 91, # 7, p. 1069 - 1074

4
[ 20651-67-6 ]
[ 79887-09-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1440 - 1446

5
[ 41492-05-1 ]
[ 1066-54-2 ]
[ 79887-09-5 ]

Reference： [1] Chemistry - A European Journal, 2018, vol. 24, # 57, p. 15303 - 15308

6
[ 1200-14-2 ]
[ 79887-09-5 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 250, p. 303 - 314

[ 79887-09-5 ] Synthesis Path-Downstream 1~38

1
[ 20651-67-6 ]
[ 79887-09-5 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1440 - 1446

3
[ 615-43-0 ]
[ 79887-09-5 ]
[ 1027340-20-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: (4-butylphenyl)acetylene With piperidine; copper(l) iodide at 20℃; for 2.5h; Stage #2: 2-iodophenylamine With piperidine at 20℃; Further stages.;
75%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	General procedure for the preparation of the alkynylanilines 2 General procedure: In a typical reaction, PdCl2(PPh3)2 (88 mg, 0.125 mmol), CuI (24 mg, 0.125 mmol) and THF (5 ml) were placed in an oven-dried, 2-neck RB flask. To this suspension, 2-iodoaniline (5.47 mg, 2.5 mmol) and triethylamine (702 μl, 5.0 mmol) were added. The reaction mixture was degassed by bubbling with argon for 15 min. Phenylacetylene (300 μl, 2.75 mmol) was then added, and the reaction mixture stirred at RT. After complete consumption of the 2-iodoanilines (~2 h, by TLC), the reaction mixture was filtered through celite, and the solvent rotary evaporated to obtain the crude product which was purified by silica gel (60-120 mesh) column chromatography using ethylacetate/ hexane (1:9, v/v) as eluent to give pure 2-phenylethynylaniline, 2a (400 mg, 83%).
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 5h; Inert atmosphere;

	With bis-triphenylphosphine-palladium(II) chloride; triethylamine In acetonitrile at 70℃; Sealed tube; Inert atmosphere; Schlenk technique;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 24h; Inert atmosphere;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere;

Reference： [1]Sakai, Norio; Annaka, Kimiyoshi; Fujita, Akiko; Sato, Asuka; Konakahara, Takeo [Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4160 - 4165]
[2]Kumaran, Elumalai; Leong, Weng Kee [Tetrahedron Letters, 2014, vol. 55, # 40, p. 5495 - 5498]
[3]Wang, Xu; Li, Jiawei; Huang, Yubing; Zhu, Jiayi; Hu, Rongrong; Wu, Wanqing; Jiang, Huanfeng [Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 10453 - 10464]
[4]Saini, Kapil Mohan; Saunthwal, Rakesh K.; Kumar, Shiv; Verma, Akhilesh K. [Organic and Biomolecular Chemistry, 2019, vol. 17, # 10, p. 2657 - 2662]
[5]Yuan, Shuo; Zhang, Dan-Qing; Zhang, Jing-Ya; Yu, Bin; Liu, Hong-Min [Organic Letters, 2020, vol. 22, # 3, p. 814 - 817]
[6]Ito, Mamoru; Onoda, Hideaki; Takaki, Asahi; Shibata, Takanori [European Journal of Organic Chemistry, 2022, vol. 2022, # 15]

4
[ 875-30-9 ]
[ 79887-09-5 ]
[ 1235885-97-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium tetrachloropalladate(II); oxygen; caesium carbonate; Trimethylacetic acid In dimethyl sulfoxide at 80℃; for 24h;

Reference： [1]Yang, Luo; Zhao, Liang; Li, Chao-Jun [Chemical Communications, 2010, vol. 46, # 23, p. 4184 - 4186]

5
[ 592-35-8 ]
[ 79887-09-5 ]
[ 100-52-7 ]
[ 1261030-44-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2437 - 2440

6
[ 588-93-2 ]
[ 79887-09-5 ]
4-propyl-4'-butyldiphenylacetylene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2009,vol. 19,p. 7525 - 7531

7
bis(acetonitrile)palladium(II) dichloride [ No CAS ]
[ 1282582-87-9 ]
[ 79887-09-5 ]
[ 534-17-8 ]
[ 564483-18-7 ]
[ 1282582-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water;	1.2) 1,4-Bis(2-(4-butylphenyl)ethynyl)-2-cyclopropylbenzene (1) 5 g (26 mmol) of 1,4-dichloro-2-cyclopropylbenzene, 9.4 g (58 mmol) of 1-n-butyl-4-ethynylbenzene, 19 g (58 mmol) of caesium carbonate, 69 mg (0.3 mmol) of bis(acetonitrile)palladium(II) chloride and 382 mg (0.8 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl are dissolved in 80 ml of dioxane under nitrogen and heated at 100 C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography and recrystallised from ethanol, giving the title compound 1 as a solid.

Reference： [1]Patent: US2012/205583,2012,A1

8
[ 657408-07-6 ]
9-methoxy-9-BBN [ No CAS ]
[ 1282582-93-7 ]
[ 79887-09-5 ]
[ 1282582-91-5 ]
[ 1282582-94-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hexamethyldisilazane;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; hexane; water;	2.3) 1,4-Bis(2-(4-butylphenyl)ethynyl)-2-cyclobutylbenzene 3 7.8 g (47.0 mmol) of 1-butyl-4-ethynylbenzene are initially introduced in 100 ml of THF under nitrogen, cooled to -78 C., and 63.32 ml (63.20 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in hexane are added dropwise. After 1 hour, 63.22 ml (63.20 mmol) of a 1M solution of 9-methoxy-9-BBN in hexane are added, and the mixture is left to stir at -78 C. for 2 hours. In a second apparatus, 6.8 g (23.45 mmol) of 5, 0.916 g (1.0 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.64 g (4.0 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl are initially introduced in 100 ml of THF. The first solution is slowly added dropwise, and the batch is heated at 100 C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography and recrystallised from isopropanol, giving the title compound 3 as a solid.

Reference： [1]Patent: US2012/205583,2012,A1

9
[ 69907-27-3 ]
[ 79887-09-5 ]
[ 1404454-56-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis-triphenylphosphine-palladium(II) chloride; sodium acetate; lithium chloride In dimethyl amine at 120℃; for 22h; Inert atmosphere; regioselective reaction;

Reference： [1]Shukla, Satya Prakash; Tiwari, Rakesh K.; Verma, Akhilesh K. [Journal of Organic Chemistry, 2012, vol. 77, # 22, p. 10382 - 10392]

10
[ 20651-67-6 ]
[ 79887-09-5 ]
[ 1469444-96-9 ]
[ 1469445-26-8 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 10121 - 10123

11
[ 20651-67-6 ]
[ 79887-09-5 ]
[ 80221-11-0 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 10121 - 10123

12
[ 79887-09-5 ]
[ 1864-94-4 ]
3-(4-(butyl)phenyl)-1-phenylpropan-2-yn-1-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3183 - 3186
Angew. Chem.,2014,vol. 126,p. 3247 - 3250,4

13
[ 773-82-0 ]
[ 79887-09-5 ]
4-(4-(4-butylphenyl)-1H-1,2,3-triazol-1-yl)-2,3,5,6-tetrafluorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium azide; copper(II) acetate monohydrate In acetonitrile at 20℃; for 8h; Schlenk technique;	General procedure for thesynthesis of the products (sodium azide, phenylacetyleneand pentafluorobenzonitrile as the example) General procedure: Sodium azide (13.0 mg, 0.20mmol) and Cu(OAc)2.H2O (4.0 mg, 10 mol %) were weighed to a Schlenk tube, and CH3CN(0.5 mL) was added. Then pentafluorobenzonitrile (42.5 mg, 0.22 mmol) and phenylacetylene (30.6 mg, 0.30mmol) were added to the tube, respectively. The mixture was stirred at roomtemperature for 8 h until it was completed (by TLC). Water (5.0 mL) was addedand the mixture was extracted with ethyl acetate (3×10.0 mL). The organicextracts were combined, dried with anhydrous magnesium sulfate and thenconcentrated in vacuo. The residue was purified on silica gel to afford the product 3a

Reference： [1]Cao, Liming; Liu, Cuibo; Tang, Xiangyang; Yin, Xuguang; Zhang, Bin [Tetrahedron Letters, 2014, vol. 55, # 36, p. 5033 - 5037]

14
[ 79887-09-5 ]
[ 20651-71-2 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 4799 - 4802

15
[ 657408-07-6 ]
[ 1634-04-4 ]
1-bromo-3-fluoro-2-propylbenzene [ No CAS ]
[ 79887-09-5 ]
[ 38050-71-4 ]
1-(4-butylphenylethynyl)-3-fluoro-2-propylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; hexane;	1.2 Synthesis of 1-(4-butylphenylethynyl)-3-fluoro-2-propylbenzene (5) Lithium bis(trimethylsilyl)amide (147 ml, 1.0 M in hexane, 0.15 mol) is added dropwise at -75 C. to a solution of 4-butylphenylacetylene (4) (CAS 79887-09-5) (24.5 g, 0.15 mol) in THF (800 ml). After 1 h, 9-methoxy-9-borabicyclo[3.3.1]nonane (147 ml, 1.0 M in hexane, 0.15 mol) is added dropwise, and the reaction mixture is stirred at this temperature for 1 h. Tris(dibenzylideneacetone)dipalladium (2.9 g, 3.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.0 g, 2.5 mmol) and 1-bromo-3-fluoro-2-propylbenzene (28.5 g, 0.13 mol) are subsequently added at -20 C., and the mixture is heated under reflux for 16 h. The work-up is carried out by addition of methyl tert-butyl ether and dist. water. After the organic phase has been separated off, the aqueous phase is re-extracted with methyl tertbutyl ether. The combined organic phases are washed with ammonium chloride solution and sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue is purified by filtration through silica gel (100% heptane), giving 1-(4-butylphenylethynyl)-3-fluoro-2-propylbenzene (5) in the form of a yellow oil.

Reference： [1]Patent: US2015/267115,2015,A1

16
[ 10135-00-9 ]
[ 79887-09-5 ]
3-((4-butylphenyl)ethynyl)benzo[b]thiophene-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 70℃;

Reference： [1]Kumar, Sonu; Cruz-Hernández, Carlos; Pal, Shilpi; Saunthwal, Rakesh K.; Patel, Monika; Tiwari, Rakesh K.; Juaristi, Eusebio; Verma, Akhilesh K. [Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10548 - 10560]

17
[ 13484-50-9 ]
[ 79887-09-5 ]
2,3,5,6-tetrakis((4-butylphenyl)ethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper(l) iodide; bis(acetonitrile)palladium(II) chloride; diisopropylamine; XPhos In 1,4-dioxane at 100℃; for 20h; Sealed tube;

Reference： [1]Petrosyan, Andranik; Ehlers, Peter; Surkus, Annette-E.; Ghochikyan, Tariel V.; Saghyan, Ashot S.; Lochbrunner, Stefan; Langer, Peter [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1442 - 1449]

18
[ 68251-77-4 ]
[ 79887-09-5 ]
C₂₃H₂₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 12h; Inert atmosphere;

Reference： [1]Meng, Lingkui; Fujikawa, Takao; Kuwayama, Motonobu; Segawa, Yasutomo; Itami, Kenichiro [Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10351 - 10355]

19
[ 13214-70-5 ]
[ 79887-09-5 ]
C₂₂H₁₉Br [ No CAS ]