[ CAS No. 25739-23-5 ] {[proInfo.proName]}

Name: 25739-23-5|4-(Phenylethynyl)benzoic acid|97%
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SKU: A657197
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Quality Control of [ 25739-23-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 25739-23-5 ]

Product Details of [ 25739-23-5 ]

CAS No. :	25739-23-5	MDL No. :	MFCD00438677
Formula :	C₁₅H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OGZUGPOTBGMCLE-UHFFFAOYSA-N
M.W :	222.24	Pubchem ID :	4308903
Synonyms :

Calculated chemistry of [ 25739-23-5 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	65.82
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.47
Log Po/w (XLOGP3) :	4.14
Log Po/w (WLOGP) :	2.86
Log Po/w (MLOGP) :	3.59
Log Po/w (SILICOS-IT) :	3.31
Consensus Log Po/w :	3.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-4.28
Solubility :	0.0116 mg/ml ; 0.0000522 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.63
Solubility :	0.0052 mg/ml ; 0.0000234 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.38
Solubility :	0.00931 mg/ml ; 0.0000419 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.16

Safety of [ 25739-23-5 ]

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 [ 25739-23-5 ]

* 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.

Downstream synthetic route of [ 25739-23-5 ]

[ 25739-23-5 ] Synthesis Path-Downstream 1~88

1
[ 25739-23-5 ]
[ 54737-75-6 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 3452,3453

2
[ 25739-23-5 ]
[ 25851-08-5 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 327 - 341
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 2722 - 2726
Angew. Chem.,2014,vol. 126,p. 2760 - 2764,5
[4]Journal of Organic Chemistry,2016,vol. 81,p. 2166 - 2173
[5]Journal of Medicinal Chemistry,2018,vol. 61,p. 9534 - 9550

3
[ 100865-20-1 ]
[ 25739-23-5 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

4
[ 619-58-9 ]
[ 536-74-3 ]
[ 25739-23-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With Cu(II)IL/Schiff base complex decorated on gamma-Fe2O3; In dimethyl sulfoxide; at 90℃; for 3h;	General procedure: In a typical run, 4-iodotoluene (1.0 mmol) and phenylacetylene(1.2 mmol) were dissolved in 2.0 mL DMSO.The catalyst (80 mg, 0.4 mol%) was added to the mixture,and the resultant mixture was stirred at 90 C under aerobic conditions. The reaction progress was monitored byTLC. Upon the reaction completion, the magnetic catalystwas separated using an external magnetic field, and then,water (5 mL) and dichloromethane (5 mL) were addedto the reaction mixture. The organic layer was separated,and the aqueous layer was extracted with further DCM.The organic layers were combined, dried over MgSO4,andthen, the solvent was removed under reduced pressure. The products were purified by silica gel column chromatography.The products were identified by 1HNMR and 13CNMRand comparison with the corresponding authentic samples
88%	With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h;Inert atmosphere;Catalytic behavior;	General procedure: A 50 mL round bottom flask was charged with aryl iodide(1 mmol), phenyl acetylene (1.5 equivalent), Cs2CO3(1.5 equiva-lent) and mixed with 5 mL DMF and 0.005 g PdCHT. The resultingmixture was subjected to reflux in N2atmosphere at 80C undercontinuous stirring. The progress of the reaction was monitoredby TLC. After the reaction was over, the catalyst was separated bysimple filtration and washed extensively with ethyl acetate. Later,the filtrate was extracted with ethyl acetate and washed with brinesolution. The organic part thus obtained was dried by Na2SO4andthe solvent was then removed by rotary evaporation under reducedpressure. The final product was purified by either recrystallizationor column chromatography methods, before analyzing results.
84%	With potassium hydroxide; In ethanol; water; at 50℃; for 24h;Green chemistry;	General procedure: Arylhalide (0.46 mmol), phenyl acetylene (0.60 mmol) and base (K2CO3 or KOH, 0.92 mmol) were dissolved in EtOH/H2O (3:1,4.00 mL) in a reaction vial. The hybrid hydrogel containing approx.8 mmol of Pd (1.7% mol) was added to the reaction mixture. The reaction vial was heated to 50 C and left to react without stirring.The progress of the reaction was monitored by TLC. After the reaction was complete (24 h), the product was extracted with diethyl ether (3e5 5 mL) and washed with water (3 20 mL). The organic phase was dried over MgSO4 and the solvent was evaporated under reduced pressure to give the crude product that was further purified by silica gel column chromatography (eluent:hexane or hexane:dichlormethane mixture). Yields of the compoundsare reported in Table 3.

With potassium acetate; In dimethylsulfoxide-d6; at 100℃;

General procedure: A two-necked flask was charged with, the aryl halide(0.180 mmol), 1,3,5-trimethoxybenzene (0.180 mmol, 30.3 mg) and KOAc (0.270 mmol, 26.5 mg). A dispersion of Fe3O4/oleic acid/Pd nanoparticles was made in DMSO-d6 (1.00 mL, 2.00 mg/mL) and was added to the two-necked flask. The acetylene (1.80 mmol) was added and the mixture was stirred for 3 h under reflux at 100 C. After stirring, the nanoparticles were isolated from the mixture with a magnet. The conversion, with respect to the desired end product,was determined by 1H NMR of the crude reaction mixture, using 1,3,5-trimethoxybenzene as an internal standard.For more detailed information: see supplementary material.

Reference： [1]Journal of the Iranian Chemical Society,2019,vol. 16,p. 2693 - 2705
[2]RSC Advances,2014,vol. 4,p. 32826 - 32833
[3]Journal of Chemical Research - Part S,2000,p. 536 - 537
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2007,vol. 46,p. 154 - 159
[5]Tetrahedron Letters,1996,vol. 37,p. 897 - 900
[6]ChemCatChem,2013,vol. 5,p. 2453 - 2461
[7]RSC Advances,2019,vol. 9,p. 20749 - 20759
[8]Journal of Molecular Catalysis A: Chemical,2016,vol. 425,p. 147 - 156
[9]Tetrahedron,2020
[10]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1984,vol. 33,p. 1433 - 1438
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1984,p. 1561 - 1566
[11]Applied Organometallic Chemistry,2018,vol. 32
[12]Tetrahedron Letters,1994,vol. 35,p. 8919 - 8922
[13]Transition Metal Chemistry,2010,vol. 35,p. 305 - 313
[14]RSC Advances,2016,vol. 6,p. 49376 - 49386
[15]Journal of Organometallic Chemistry,2019,vol. 904

5
[ 25739-23-5 ]
[ 18107-18-1 ]
[ 42497-80-3 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6173 - 6177

6
[ 536-74-3 ]
[ 74-11-3 ]
[ 25739-23-5 ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 6173 - 6177

7
[ 536-74-3 ]
iodobenzoic acid attached to cross-linked polystyrene [ No CAS ]
[ 25739-23-5 ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 133 - 141

8
[ 25739-23-5 ]
[ 86970-24-3 ]
C₂₀H₁₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80 - 90%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 18h;	Example 7:; Part A:; To a solution of amine (compounds 53, 58, and 63) (0.18 mmol) and HATU (86 mg, 0.23 mmol) in DMF (2 ml_) was added compound 50 (54 mg, 0.24 mmol) and diisopropylethylamine (72 mul_, 0.41 mmol). The reaction mixture was stirred at room temperature for 18 hours. LC-MS analysis of the reaction indicated that the reaction was complete. The volatlles were removed in vacuo, ethyl acetate was added, and the organic solution washed successively with saturated NaHCO3 (x1), water (x1), brine (x1), dried over magnesium sulfate and concentrated. Purification by preparative LC afforded compounds 64 - 66 (80 - 90 % yield).

Reference： [1]Patent: WO2008/27466,2008,A1 .Location in patent: Page/Page column 57-58

9
[ 25739-23-5 ]
[ 857167-91-0 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

10
[ 25739-23-5 ]
4-Diazoacetyl-tolan [ No CAS ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

11
[ 25739-23-5 ]
[ 42196-54-3 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

12
[ 25739-23-5 ]
[ 860217-52-3 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

13
[ 25739-23-5 ]
4,4'-Bis-phenethinyl-stilben-α-carbonsaeure [ No CAS ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

14
[ 32555-96-7 ]
[ 25739-23-5 ]

Reference： [1]Chemische Berichte,1960,vol. 93,p. 990 - 998

15
[ 25739-23-5 ]
[ 3306-62-5 ]
[ 228707-94-6 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With thionyl chloride; In pyridine; dichloromethane; ethyl acetate; benzene;	Reference Example 47 4-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide A solution of 3.00 g (13.5 mmol) of <strong>[25739-23-5]4-phenylethynylbenzoic acid</strong> and 2 ml of thionyl chloride in benzene (30 ml) was heated under reflux for 2 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride (30 ml). The obtained solution was added dropwise to a solution of 2.32 g (13.50 mmol) of 2-aminobenzenesulfonamide in pyridine (50 ml) under cooling with ice. The obtained mixture was stirred at room temperature for 18 hours. Methylene chloride was evaporated under reduced pressure. The residue was dissolved in ethyl acetate and then the obtained solution was washed with 1 N aqueous hydrochloric acid solution, water and saturated aqueous sodium chloride solution in that order. After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 4.00 g (yield: 78.7%) of the title compound. 1H-NMR (DMS O-d6) delta: 7.34-7.39 (1H, m), 7.44-7.50 (3H, m), 7.58-7.70 (3H, m), 7.77 (2H, d, J=8 Hz), 7.92 (1H, dd, J=8 Hz, 1 Hz), 7.97 (2H, d, J=8 Hz), 8.44 (1H, d, J=8 Hz), 10.50 (1H, br-s)
78.7%	With pyridine; thionyl chloride; In dichloromethane; ethyl acetate; benzene;	Reference Example 10 4-Phenylethynyl-N-(2-sulfamoylphenyl)benzamide A benzene (30 ml) solution containing 3.00 g (13.5 mmol) of <strong>[25739-23-5]4-phenylethynylbenzoic acid</strong> and 2 ml of thionyl chloride was heated under reflux for 2 hours and then the solvent was evaporated under a reduced pressure. The resulting residue was dissolved in methylene chloride (30 ml), this solution was added dropwise under ice-cooling to a pyridine (50 ml) solution containing 2.32 g (13.50 mmol) of 2-aminobenzenesulfonamide, the mixture was stirred at room temperature for 18 hours and then methylene chloride was evaporated under a reduced pressure. The resulting residue was dissolved in ethyl acetate, washed with a 1 N hydrochloric acid aqueous solution, water and saturated brine in that order and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. The resulting residue was recrystallized from ethyl acetate-hexane to obtain 4.00 g (yield: 78.7%) of the title compound. NMR (DMSO-d6) delta: 7.34-7.39 (1H, m), 7.44-7.50 (3H, m), 7.58-7.70 (3H, m), 7.77 (2H, d, J=8Hz), 7.92 (1H, dd, J=8Hz, 1Hz), 7.97 (2H, d, J=8Hz), 8.44 (1H, d, J=8Hz), 10.50 (1H, br-s)

Reference： [1]Patent: US2003/191323,2003,A1
[2]Patent: US6555584,2003,B1

16
[ 3373-59-9 ]
[ 25739-23-5 ]
3-hydroxy-2-(4-phenylethynylbenzoylamino)butyric acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
~ 100%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 12h;	Preparation of 3-hydroxy-2-(4-phenylethvnyl-benzoylamino)-butyric acid methyl ester(4). A solution of threonine methyl ester (1.66 g, 9.8 mmol) and DIEA (1.53 ml,8.8 mmol) in DMF (10 ml) was added to a stirred solution of (3) (1.55 g, 7.0 mmol) and DIEA (1.53 ml, 8.8 mmol) in DMF (11 ml) at rt. After 12 h, the reaction was diluted with EtOAc (300 ml) and washed with 0.5M HCl (2x60 ml), sat. aq. NaHCO3 (60 ml), 50% diluted brine (60 ml), sat. brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. Upon drying in vacuo, 2.34 g of white solid (4) was obtained (approximately quantitative yield in 99% purity).

Reference： [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 87

17
[ 42497-80-3 ]
[ 25739-23-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water; sodium hydroxide; In methanol; at 70℃; for 1h;	The 4-iodo-benzoic acid methyl ester 1 (20.0g, 76.34mmol), ethynyl-benzene 2 (8.56g, 83.96mmol),PdCl2(PPh3)2 (0.65g, 0.92mmol), and CuI (0.35g, 1.83mmol) were mixed with THF (110ml) in a round bottom underargon. The dry THF was sparged with dry, oxygen-free argon for at least 5 min. immediately before use. The reactionwas cooled to 10 C and TEA (16ml) was added. The cooling bath was removed and the reaction was stirred at RTunder argon. After 2.5h, the reaction was diluted with EtOAc (400 ml) and the solids were filtered off through a pad ofcelite. The organic filtrate was washed with 1M HCl (60ml), sat. aq. NaHCO3 (60ml), water (60ml), brine (60ml), driedwith Na2SO4, filtered and concentrated under reduced pressure. The crude solid methyl ester was dissolved in MeOH(400ml), 6M NaOH (30ml) and water (50ml). The reaction was stirred at 70 C until a clear solution was formed (about1h) The reaction could be followed by LCMS. The reaction was cooled and diluted with water (500ml) and hexane(100ml). The pH was adjusted to pH 6-7. The white solid that formed was collected and washed with water (3x60ml)and hexane (3x60ml). The solid 3 was dried in vacuo yielding 17.3g (approximately quantitative yield in 99% purity).
		Preparation of 4-Phenylethvnyl -benzoic acid (3). 4-Iodo-benzoic acid methyl ester (1) (20.0 g, 76.34 mmol), ethynyl -benzene (2) (8.56 g, 83.96 mmol), PdCl2(PPh3)2 (0.65 g, 0.92 mmol), and CuI (0.35 g, 1.83 mmol) were mixed with THF (110 ml) in a round bottom under argon. The dry THF was sparged with dry, oxygen-free argon for at least 5 min. immediately before use. The reaction was cooled to 10 C. and TEA (16 ml) was added. The cooling bath was removed and the reaction was stirred at RT under argon. After 2.5 h, the reaction was diluted with EtOAc (400 ml) and the solids were filtered off through a pad of celite. The organic filtrate was washed with 1 M HCl (60 ml), sat. aq. NaHCO3 (60 ml), water (60 ml), brine (60 ml), dried with Na2SO4, filtered and concentrated under reduced pressure. The crude solid methyl ester was dissolved in MeOH (400 ml), 6M NaOH (30 ml) and water (50 ml). The reaction was stirred at 70 C. until a clear solution was formed (about 1 h). The reaction could be followed by LCMS. The reaction was cooled and diluted with water (500 ml) and hexane (100 ml). The pH was adjusted to pH 6-7. The white solid that formed was collected and washed with water (3x60 ml) and hexane (3x60 ml). The solid (3) was dried in vacuo yielding 17.3 g (approximately quantitative yield in 99% purity).

Reference： [1]Patent: EP2295402,2015,B1 .Location in patent: Paragraph 0192; 0193
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9534 - 9550
[3]ChemMedChem,2016,p. 2147 - 2154
[4]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 86-87

18
[ 124-38-9 ]
[ 1034330-14-7 ]
[ 25739-23-5 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2697 - 2700
[2]Chemical Communications,2012,vol. 48,p. 6292 - 6294

19
[ 109-01-3 ]
[ 25739-23-5 ]
[ 381675-39-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3275 - 3278

20
[ 626-58-4 ]
[ 25739-23-5 ]
[ 381675-35-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3275 - 3278

21
[ 25739-23-5 ]
[ 27757-86-4 ]
[ 1174028-90-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3275 - 3278

22
[ 2033-24-1 ]
[ 25739-23-5 ]
C₂₁H₁₆O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 66h;Cooling with ice;	(1) 2, 2-dimethyl-5-[4-(phenylethynyl)benzyl]-1, 3-dioxane-4, 6-dione To a mixture of Meldrum's acid (688 mg) and <strong>[25739-23-5]4-phenylethynylbenzoic acid</strong> (955 mg) in methylene chloride (30 mL) was added a solution of 4-dimethylaminopyridine (830 mg) and N, N'-dicyclohexylcarbodiimide (976 mg) in methylene chloride (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 66 hr. Insoluble material was removed by filtration, and the filtrate was washed with 10% potassium hydrogen sulfate (30 mL) and saturated brine and concentrated under reduced pressure. The residue was dissolved in acetic acid (5 mL), and the solution was cooled to 0C. Sodium borohydride (408 mg) was added, and the mixture was stirred at room temperature for 6 hr. Water (50 mL) was added to the reaction mixture, and the mixture was extracted with methylene chloride (50 mL*2). The organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was washed with isopropanol, and the resulting precipitate was collected by filtration to give the title compound (654 mg) as a white solid. 1H-NMR(300MHz, CDCl3)delta1.56(3H, s), 1.75(3H, s), 3.50(2H, d, J = 4.8Hz), 3.76(1H, t, J = 4.8Hz), 7.28-7.40(5H, m), 7.44-7.55(4H, m).

Reference： [1]Patent: EP2172450,2010,A1 .Location in patent: Page/Page column 61

23
4-(phenylethynyl)benzoic acid Wang resin [ No CAS ]
[ 25739-23-5 ]

Reference： [1]Synlett,2010,p. 2639 - 2643

24
[ 619-58-9 ]
[ 637-44-5 ]
[ 25739-23-5 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 9049 - 9051

25
[ 1942-31-0 ]
[ 25739-23-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 327 - 341

26
[ 25739-23-5 ]
(2RS,3SR)-1-(4-phenylethynylbenzoyl)piperazine-2,3-dicarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 327 - 341

27
[ 25739-23-5 ]
(2RS,3SR)-1-(4-(2-phenylethyl)benzoyl)piperazine-2,3-dicarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 327 - 341

28
[ 536-74-3 ]
[ 25739-23-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 327 - 341
[2]Journal of Organic Chemistry,2013,vol. 78,p. 12703 - 12709
[3]Patent: EP2295402,2015,B1
[4]ChemMedChem,2016,p. 2147 - 2154
[5]Patent: WO2008/154642,2008,A2

29
[ 619-44-3 ]
[ 536-74-3 ]
[ 25739-23-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2362 - 2367
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 9534 - 9550

30
[ 25739-23-5 ]
[ 1428857-72-0 ]