[ CAS No. 119301-59-6 ] {[proInfo.proName]}

Name: 119301-59-6|Tetrakis(4-hydroxyphenyl)ethylene|98%
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Quality Control of [ 119301-59-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 119301-59-6 ]

Product Details of [ 119301-59-6 ]

CAS No. :	119301-59-6	MDL No. :	MFCD28901376
Formula :	C₂₆H₂₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QQUZHNPGWNIYMK-UHFFFAOYSA-N
M.W :	396.43	Pubchem ID :	10200771
Synonyms :

Calculated chemistry of [ 119301-59-6 ]

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	4.0
Molar Refractivity :	118.88
TPSA :	80.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.66
Log Po/w (XLOGP3) :	6.54
Log Po/w (WLOGP) :	5.52
Log Po/w (MLOGP) :	3.96
Log Po/w (SILICOS-IT) :	4.71
Consensus Log Po/w :	4.68

Druglikeness

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

Water Solubility

Log S (ESOL) :	-6.75
Solubility :	0.0000711 mg/ml ; 0.000000179 mol/l
Class :	Poorly soluble
Log S (Ali) :	-8.04
Solubility :	0.00000364 mg/ml ; 0.0000000092 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-7.66
Solubility :	0.00000861 mg/ml ; 0.0000000217 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.61

Safety of [ 119301-59-6 ]

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 [ 119301-59-6 ]

* 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 [ 119301-59-6 ]

[ 119301-59-6 ] Synthesis Path-Downstream 1~88

1
[ 10019-24-6 ]
[ 119301-59-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With boron tribromide; In dichloromethane; at -20 - 20℃; for 40h;	A certain amount of BBr3 (4mL, 44.2mmol) was first added in 50mL of dry DCM solution containing Compound 2 (2.00g, 4.42mmol) at -20C. The mixture was stirred for 40h at room temperature, and then was concentrated under vacuum. The mixture was poured into 100mL water and stirred for 5min after adding 3ml ethanol, and then massive white precipitates were generated. The final product was obtained in 97% yield (1.7g) after filtration and drying. 1H NMR (600MHz, DMSO-d6) δ 9.24 (s, 4H), 6.70 (d, J=12Hz, 8H), 6.48 (d, J=12Hz, 8H). 13C NMR (150MHz, DMSO-d6) δ 155.34, 137.67, 135.05, 131.94, 114.47. HRMS (ESI) m/z: [M+Na+] 419.1249, (calcd. for C26H28O4, 396.1349).
95%	With boron tribromide; In dichloromethane; at 0 - 20℃;	2MDCM solution of BBr3 was added dropwise to a solution oftetrakis(4-methoxyphenyl)ethane (0.65g, 1.43 mmol) in DCM while keeping at 0C. After the addition was completed, reaction mixture was allowed to stir at room temperature. The progress of the reaction was monitored by TLC and when TLC showed no starting material, reaction mixture was hydrolyzed by dropwise addition of H20 (10 mL). After the filtration, the precipitate was washed with H20 and recrystallized from acetone/ H20(1/1) giving the target compound 4(0.587 g, 95%).1HNMR (400 MHz, d-DMSO): d 6.70 (d, J = 8.51 Hz, 8H), 6.47 (d, J =8.55 Hz, 8H). 13C NMR (100 MHz, d-DMSO): d 160.0, 142.3, 139.9, 136.8, 119.3ppm. MS(TOF- ESI): m/z: Calcd for C26H20O4: 397.14344[M+H]+, Found: 397.15629 [M+H]+ , Δ=-4.67 ppm.
92%	With boron tribromide; In dichloromethane; chloroform; at 20℃; for 12h;Cooling with ice;	The compound 2 (6.01 g-13.3mmol) was dissolved in 100 ml of chloroform, and the methylene chloride solution (37.2 mL, 74.4mmol) of 2MBBr3was dropped slowly, cooling by the ice bath which put in the freezing mixture. After removing the ice bath and agitating at a room temperature for 12 hours, 50 ml of water was added. The sediments which arose were collected and it recrystallized by acetone:water =1:1. 5.26 g of compounds 3 were obtained as white crystals. 92% of yield.

88%	With boron tribromide; In dichloromethane; at -78 - 20℃;Inert atmosphere;	2) Under the protection of argon,The above 3.0 g of 4,4',4",4"'-tetramethoxytetrastyrene was dissolved in 25 mL of dichloromethane.Dissolve 5.0 mL of BBr3 in 10 mL of dichloromethane at -78 C.a mixture of boron tribromide and dichloromethane is added dropwise to the reaction apparatus.After the dropwise addition was completed, the mixture was stirred at -78 C for 30 minutes.After that, it was returned to room temperature, stirred at room temperature overnight, and after the reaction was completed, it was added dropwise.Add 30mL of distilled water, there will be a purple-red solid precipitation, suction filtration,Wash with dichloromethane, dry,2.3 g of a purple-red solid 4,4',4",4"'-tetrahydroxytetrastyrene was obtained in a yield of 88%.
82.3%	With boron tribromide; In chloroform; at 0 - 20℃; for 12h;	Compound 3 was prepared according to the previous report. [37b] BBr3 (3.80 mL, 40.0 mmol) was added to a cooled solution of compound 2 (4.53 g, 10.0 mmol) in CHCl3 (200 mL) at 0 C and the resulting deep red mixture was stirred for 2 h at. After removal of the cooling bath, the mixture was stirred for 10 h at room temperature and then quenched by water. The precipitate was filtered, washed with H2O and CH2Cl2. Recrystallization from EtOH/H2O (1:1) obtained 3.29 g (yield 82.3%) of a light pink solid. 1H NMR (400 MHz, DMSO-d6, 298 K) δ (ppm): 9.22 (s, 4H), 6.70 (d, J = 8 Hz, 8H), 6.47 (d, J = 12 Hz, 8H).
80%	With boron tribromide; In dichloromethane; at 20℃; for 18h;Cooling with ice; Inert atmosphere;	A solution of TPE-OMe (2.0 g) in anhydrous dichloromethane (40 ml) was added and cooled in an ice water bath, and boron tribromide (1.7 ml) was poured under a nitrogen atmosphere, and stirred in an ice water bath for 2 hours. Stirring was continued for 16 hours at room temperature; after completion of the reaction, deionized water was added dropwise to the ice water bath to hydrolyze it, and a purple solid was observed to precipitate. Filtration, washing, drying and weighing (1.40 g, 80%)
76.1%	With boron tribromide; In dichloromethane; at 20℃; for 20h;Inert atmosphere;	Add 0.5g of compound A to a 100mL three-necked flask, add ultra-dry solvent CH2Cl2 (10mL) under N2, stir evenly, add ice salt bath, add 2.2g of boron tribromide, dark purple, after 15 minutes, The ice salt bath was removed, stirred at room temperature for 20 hours, added with an ice bath, and quenched with dropwise addition of methanol. After no white smoke was released, water was added until no precipitate formed. The solid was collected by suction filtration, washed with water (50mLx2) CH2CI2 (50mLX2) washed, suction filtration to give a solid which was vacuum oven dried to give a purple solid (compound B), a yield of 76.1%.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 8804 - 8809
[2]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2019,vol. 223
[3]Tetrahedron Letters,2014,vol. 55,p. 456 - 459
[4]Chemistry - An Asian Journal,2011,vol. 6,p. 2376 - 2381
[5]Chemical Communications,2012,vol. 48,p. 8090 - 8092
[6]Chemical Communications,2015,vol. 51,p. 10210 - 10213
[7]Patent: JP6081152,2017,B2 .Location in patent: Paragraph 0015; 0030; 0032
[8]Chemical Communications,2014,vol. 50,p. 9122 - 9125
[9]Journal of Materials Chemistry C,2015,vol. 3,p. 11850 - 11856
[10]Patent: CN109053583,2018,A .Location in patent: Paragraph 0038-0040
[11]Tetrahedron,2020,vol. 76
[12]Patent: CN108849908,2018,A .Location in patent: Paragraph 0036; 0039
[13]Patent: CN109134384,2019,A .Location in patent: Paragraph 0027; 0029
[14]Proceedings of the Royal Society of London. Series B, Biological sciences,1945,vol. 132,p. 83,95
[15]Journal of the American Chemical Society,1958,vol. 80,p. 5055
Journal of the American Chemical Society,1960,vol. 82,p. 6427
[16]RSC Advances,2016,vol. 6,p. 50673 - 50679
[17]Chemical Communications,2017,vol. 54,p. 200 - 203
[18]Dyes and Pigments,2021,vol. 193

2
[ 119301-59-6 ]
3,5,3',5',3'',5'',3''',5'''-octabromo-4,4',4'',4'''-ethenediylidene-tetra-phenol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 5055
Journal of the American Chemical Society,1960,vol. 82,p. 6427

3
[ 499-44-5 ]
[ 119301-59-6 ]
C₂₆H₂₀O₄*2C₁₀H₁₂O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 925 - 929

4
[ 108-86-1 ]
[ 119301-59-6 ]
tetrakis(4-phenoxyphenyl)ethene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 3395 - 3404

5
[ 119301-59-6 ]
[ 108-24-7 ]
tetrakis(4-acetoxyphenyl)ethene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 3395 - 3404

6
[ 119301-59-6 ]
[ 98-88-4 ]
tetrakis(4-benzoyloxyphenyl)ethene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 3395 - 3404

7
[ 119-61-9 ]
[ 611-99-4 ]
4,4’-(2,2-diphenylethene-1,1-diyl)diphenol [ No CAS ]
[ 119301-59-6 ]
[ 632-51-9 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 9873 - 9876

8
[ 17435-03-9 ]
[ 119301-59-6 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 5055
Journal of the American Chemical Society,1960,vol. 82,p. 6427

9
[ 119301-59-6 ]
tetrakis-(3,5-dibromo-4-methoxy-phenyl)-ethene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 5055
Journal of the American Chemical Society,1960,vol. 82,p. 6427

10
[ 611-99-4 ]
[ 119301-59-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	TiCl4; In tetrahydrofuran;	Example 5 1,1,2,2-tetrakis(4-hydroxyphenyl)ethylene (DHTPE) A suspension of 4,4'-dihydroxybenzophenone (3.0 g, 14.0 mmol), 1 equiv of TiCl4 (1.54 ml, 14.0 mmol), and 2 equiv of Zn dust (1.83 g, 28.0 mmol) in 100 ml of dry THF was refluxed for 20 h. The reaction mixture was cooled to room temperature and filtered. The filtrates were evaporated and the crude product was purified by a silica gel column using ethyl acetate (EA)(EA) as eluent. DHTPE was obtained as slight yellow powder of 83% yield.
83%	TiCl4; In tetrahydrofuran; ethyl acetate;	Example 5 1,1,2,2-tetrakis(4-hydroxyphenyl)ethylene (DHTPE) A suspension of 4,4'-dihydroxybenzophenone (3.0 g, 14.0 mmol), 1 equiv of TiCl4 (1.54 ml, 14.0 mmol), and 2 equiv of Zn dust (1.83 g, 28.0 mmol) in 100 ml of dry THF was refluxed for 20 h. The reaction mixture was cooled to room temperature and filtered. The filtrates were evaporated and the crude product was purified by a silica gel column using ethyl acetate (EA) as eluent. DHTPE was obtained as slight yellow powder of 83% yield.
83%	With titanium tetrachloride; zinc; In tetrahydrofuran; for 20h;Reflux;	A suspension of 4,4′-dihydroxybenzophenone (3.0 g, 14.0 mmol), 1 equiv of TiCl4 (1.54 ml, 14.0 mmol), and 2 equiv of Zn dust (1.83 g, 28.0 mmol) in 100 ml of dry THF was refluxed for 20 h. The reaction mixture was cooled to room temperature and filtered. The filtrates were evaporated and the crude product was purified by a silica gel column using ethyl acetate (EA) as eluent. DHTPE was obtained as slight yellow powder of 83% yield. Characterization data of DHTPE: 1H NMR (300 MHz, d-DMSO), δ (ppm): 9.24-8.94 (br), 7.07-7.04 (d, 4H), 6.95-6.95 (d, 4H), 6.70-6.56 (m, 4H), 6.47-6042 (t, 4H). 13C NMR (75 MHz, CDCl3), δ (ppm): MS (FAB), m/e: 391.2 ([M-4H]+, calcd. 392.1).

76%	With titanium tetrachloride; zinc; In tetrahydrofuran; at -10℃; for 24h;Inert atmosphere; Reflux;	Zinc (2.73 g, 42.0 mmol) and anhydrous THF (80 mL) were placed in a 250-mL two-neck flask and cooled to below 10 C under a N2 at-mosphere. TiCl4 (2.34 mL, 21.5 mmol) was added slowly and then the mixture was stirred for 30 min at 10 C before heating at 70 C for 3 h with stirring, under a N2 atmosphere. A solution of 4,4 0 -dihydrox-ybenzophenone (3.00 g, 14.0 mmol) in dry THF (30 mL) was added dropwise and then the mixture was heated under reflux for 24 h. Aqueous K2CO3 (10 wt %, 50 mL) was poured into the mixture to quench the reaction. The organic phase was separated, and the aqueous phase extracted with EtOAc (3 30 mL). The combined organic phases were concentrated to afford an oily residue. Recrystallization (acetone/H2O) afforded a white powder (2.10 g, 76%). FTIR (KBr, cm 1): 3650 - 3200 (O - H stretching) and 1611 (C -- C stretching). 1H NMR (DMSO - d6, 25 C, 500 MHz): δ (ppm) 6.48 (d, J 8.4 Hz, 8H), 6.70 (d, J 8.4 Hz, 8H), 9.22 (s, 4H, OH). 13C NMR (DMSO - d6, 25 C, 500 MHz): δ (ppm) 115.12, 132.73, 135.84, 138.45, 156.26.
72%	With pyridine; titanium tetrachloride; zinc; In tetrahydrofuran; at -5℃; for 8h;Inert atmosphere; Reflux;	A three-necked flask equipped with a magnetic stirrer was charged with zinc powder (3.1 g, 47 mmol) and 30 mL anhydrous THF under nitrogen atmosphere. The mixture was cooled to 0 to -5 C and TiCl4 (2.6 mL, 23.5 mmol) was slowly added by a syringe. The suspension was warmed to room temperature and stirred for 30  min, then heated at reflux for 2.5 h. The mixture was again cooled to 0 to -5 C, charged with pyridine (0.9  mL, 11.3  mmol) and stirred for 10 min. The solution of 4,4ʹ-dihydroxybezophenone (1 g, 4.7 mmol) in 10 mL of THF was added slowly. After addition, the reaction mixture was heated at reflux for 8 h. The reaction was quenched by addition of 10% aqueous K2CO3 solution and worked up with CHCl3. The organic layer was collected and concentrated. The crude product was purified by column chromatography using 100-200 silica gel and 2:5 ethyl acetate in petroleum ether (60-80) as an eluent to afford the desired product (3). Off-white solid, yield: 72%; 1H NMR (300 MHz, DMSO-d6): δ (ppm) 6.48 (d, J = 8.4 Hz, 8H), 6.70 (d, J = 8.4 Hz, 8H), 9.22 (s, 4H, exchangeable); 13C NMR (75 MHz, DMSO-d6): δ (ppm) 114.9, 132.4, 135.5, 138.2, 155.8; ESI-MS: m/z 419 [M + Na]+; Anal. Calcd. for C26H20O4: C, 78.77; H, 5.09; Found: C, 78.92; H, 5.11.
55%	With titanium tetrachloride; zinc; In tetrahydrofuran; for 24h;Inert atmosphere; Reflux;	The 1.700 g (26.5 mmol) zinc powder is added to a 50 ml water removal THF three-port in round bottomed flask stirring. The mixture using ice bath cooling to 0 C after, under the protection of nitrogen, for pipette slowly dropping 1.4 ml (13.0 mmol) of titanium tetrachloride, goes to the ice-bath withdraw the end of the dropping, stirring at room temperature 10 min, reheat reflux 2.5 h, stop heating, cooling to room temperature, then the 3.000 g (6.6 mmol) 4, 4' - dihydroxy benzophenone dissolved in water removal THF dropping, and milling to continue to heating reflux after 1 day, completion of the reaction, cooling to room temperature, slowly adding dilute hydrochloric acid aqueous solution and stirring, filtering, the ethyl acetate extract 3 × 50 ml, drying, filtering, filtrate and steaming and to remove the ethyl acetate. Obtaining pink solid crude product, acetone purification, to obtain the solid 3.142 g, yield: 55%.

Reference： [1]Chemical Communications,2016,vol. 52,p. 12466 - 12469
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[3]Patent: US2008/220407,2008,A1
[4]Patent: US2012/172296,2012,A1
[5]Patent: US9279806,2016,B2 .Location in patent: Page/Page column 57
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[10]Patent: CN108822084,2018,A .Location in patent: Paragraph 0018; 0019
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[13]RSC Advances,2016,vol. 6,p. 4478 - 4482
[14]RSC Advances,2016,vol. 6,p. 107622 - 107627
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11
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[ 119301-59-6 ]
[ 1166400-22-1 ]