[ CAS No. 13021-19-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 13021-19-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13021-19-7 ]

SDS Specification

Alternatived Products of [ 13021-19-7 ]

Product Details of [ 13021-19-7 ]

CAS No. :	13021-19-7	MDL No. :	MFCD28404533
Formula :	C₂₀H₁₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VBXMYYRFSXQGSU-UHFFFAOYSA-N
M.W :	290.36	Pubchem ID :	12455995
Synonyms :

Safety of [ 13021-19-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13021-19-7 ]

* 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 [ 13021-19-7 ]

[ 13021-19-7 ] Synthesis Path-Downstream 1~10

1
[ 106-37-6 ]
[ 5720-07-0 ]
[ 13021-19-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; C₁₇H₁₅N₄O₃S^(1-)*Na⁽¹⁺⁾; palladium dichloride In water at 100℃; for 6h; Inert atmosphere; Green chemistry;
95%	With potassium carbonate In pyridine for 3h; Heating;
90%	With potassium phosphate; [(N,N-bis(diphenylphosphanylmethyl)-2-aminopyridine)PdCl₂] In ethanol; N,N-dimethyl-formamide at 78℃; for 1.5h; Inert atmosphere; Schlenk technique;	3 General procedure for the Suzuki-Miyaura reaction General procedure: The ligand bdppmapy (4.9 mg, 0.01 mmol) and PdCl2(1.8 mg,0.01 mmol) were added to a Schlenk tube containing a magnetic stirrer bar, and then degassed DMF (1 mL) was added. The mixture was stirred 3h at room temperature. 40-Bromoacetophenone(199 mg,1 mmol), 4-methoxyphenylboronic acid (228 mg,1.5 mmol),and K3PO4 (637 mg, 3 mmol) were added to another Schlenk tubewith a magnetic stirrer bar. The dissolved mixture of bdppmapy/PdCl2(2mL, 0.00002 mmol) was transferred to the Schlenk tube of reactants by syringe. Then, ethanol (4 mL) was added. The reaction mixture was heated at reflux for 1.5 h. At the end of the reaction, the solution was cooled to room temperature and water (5 mL) was added. The mixture solution was extracted with ethyl acetate (35 mL) and the organic layer was dried over magnesium sulfate.The dried solution was filtered and reduced to approx. 1-2ml under vacuum, then purified with silica gel chromatography to give the corresponding product with an isolated yield.

84%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene for 24h; Inert atmosphere; Reflux;
75%	Stage #1: 1.4-dibromobenzene; 4-methoxyphenylboronic acid With potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; water for 0.5h; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at 100℃; for 24h;	1.1 Preparation of 4,4"-dimethoxyterphenylene Dibromo benzene (1.0 g, 4.2 mmol) was dissolved in xylene (120 ml) and 4-methoxyphenylboronic acid (1.6 g, 10.5 mmol) dissolved in 2 M aqueous potassium carbonate solution (5.3 ml) and ethanol (17 ml) Were sequentially added. After 30 minutes, tetrakis triphenylphosphine (Pd (PPh3) 4, 0.97 g, 4.4 mmol) was added, the temperature was raised to 100 , and the mixture was stirred for 24 hours. After that, After cooling to room temperature, the reaction mixture was poured into excess water to terminate the reaction, and the solid was washed with distilled water, dichloromethane and methanol three times and dried to obtain the target compound (0.9 g, 75%) as a white solid .

Reference： [1]Li, Qi; Zhang, Li-Ming; Bao, Jia-Jing; Li, Hong-Xi; Xie, Jing-Bo; Lang, Jian-Ping [Applied Organometallic Chemistry, 2014, vol. 28, # 12, p. 861 - 867]
[2]Tao, Xiaochun; Zhao, Yinyan; Shen, Dong [Synlett, 2004, # 2, p. 359 - 361]
[3]Ning, Jin-Jiao; Wang, Jian-Feng; Ren, Zhi-Gang; Young, David James; Lang, Jian-Ping [Tetrahedron, 2015, vol. 71, # 23, p. 4000 - 4006]
[4]Jankowiak, Aleksandra; Kaszynski, Piotr; Tilford, William R.; Januszko, Adam; Ohta, Kiminori; Nagamine, Takashi; Endo, Yasuyuki [Beilstein Journal of Organic Chemistry, 2009, vol. 5]
[5]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR101527162, 2015, B1 Location in patent: Paragraph 0084; 0086; 0087

2
[ 106-37-6 ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 22%	With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h;	Catalysis experiments and gas chromatographic analysis of the reaction mixtures General procedure: Stock solutions of the catalysts (Na2[Pd(HSS)], Na2[Pd(PrHSS)], Na2[Pd(BuHSS)],Na2[Pd(dPhHSS)], rac-Na2[Pd(CyHSS)], Na2[Pd(cis-CyHSS)]) Na2[Pd(trans-CyHSS)]) were prepared by dissolving 5.0×10-7 mol complex in 6 mL water. In general, 0.5 mmol aryl-halide, 0.75 mmol boronic acid derivative (1.5 mmol in the reactions of aryl-dihalides), and 0.5 mmolbase (Cs2CO3) were used in each reaction. Good quality distilled water was used as solvent, the organic phase was comprised of the substrates. 3 mL of water was used in each reaction. The reactions were carried out at 80 °C in 30-120 min reaction time. At the end of the reactions, the mixtures were allowed to cool to room temperature and then were extracted by chlorofom (2 mL). After separation of the phases (15-20 min) the organic phase was removed by a Pasteur pipette and filtered through a short MgSO4 plug.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In methanol; toluene Heating;

Reference： [1]Bunda, Szilvia; Joó, Ferenc; Kathó, Ágnes; Udvardy, Antal; Voronova, Krisztina [Molecules, 2020, vol. 25, # 17]
[2]Sinclair, David J.; Sherburn, Michael S. [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3730 - 3733]

3
[ 3365-85-3 ]
[ 13021-19-7 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 634

4
4-bromophenyl 2,3,4,5,6-pentafluorobenzenesulfonate [ No CAS ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]
C₁₉H₁₁F₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate In <i>tert</i>-butyl alcohol at 28℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;	4. Chemoselective Suzuki-Miyaura Cross-Coupling of ArOPFBs General procedure: To a Schlenk tube equipped with a magnetic stirring bar and a septum was charged K3PO4.H2O (3 mmol, 3 equiv), aryl pentafluorobenzene sulfonates - 1 (0.5 mmol, 1.0 equiv), aryl boronic acid (0.5 mmol, 1.0 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 mol%). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inert atmosphere, tert-Butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was kept on a magnetic stirrer and stirred at room temperature 12h. The reaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was passed through a plug of silica gel and concentrated under reduced pressure. The ratio of products formed were confirmed by GCMS (FID). The residue was then purified through silica gel (230 - 400 mesh) column chromatography using 1-5% ethyl acetate in petroleum ether to afford the product.

Reference： [1]Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Nagaraj, Archana; Rangappa; Shashikanth, Sheena [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5106 - 5111]

5
[ 106-39-8 ]
[ 13139-86-1 ]
[ 13021-19-7 ]
[ 58970-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 79% 2: 8%	Stage #1: 4-methoxyphenyl magnesium bromide With titanium(IV) tetraethanolate; phenol In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: bromochlorobenzene With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran; toluene at 20 - 78℃; Inert atmosphere;

Reference： [1]Wang, Lei; Wei, Yi-Ming; Zhao, Yan; Duan, Xin-Fang [Journal of Organic Chemistry, 2019, vol. 84, # 9, p. 5176 - 5186]

6
[ 589-87-7 ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 14% 2: 64%	With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h;	Catalysis experiments and gas chromatographic analysis of the reaction mixtures General procedure: Stock solutions of the catalysts (Na2[Pd(HSS)], Na2[Pd(PrHSS)], Na2[Pd(BuHSS)],Na2[Pd(dPhHSS)], rac-Na2[Pd(CyHSS)], Na2[Pd(cis-CyHSS)]) Na2[Pd(trans-CyHSS)]) were prepared by dissolving 5.0×10-7 mol complex in 6 mL water. In general, 0.5 mmol aryl-halide, 0.75 mmol boronic acid derivative (1.5 mmol in the reactions of aryl-dihalides), and 0.5 mmolbase (Cs2CO3) were used in each reaction. Good quality distilled water was used as solvent, the organic phase was comprised of the substrates. 3 mL of water was used in each reaction. The reactions were carried out at 80 °C in 30-120 min reaction time. At the end of the reactions, the mixtures were allowed to cool to room temperature and then were extracted by chlorofom (2 mL). After separation of the phases (15-20 min) the organic phase was removed by a Pasteur pipette and filtered through a short MgSO4 plug.

Reference： [1]Bunda, Szilvia; Joó, Ferenc; Kathó, Ágnes; Udvardy, Antal; Voronova, Krisztina [Molecules, 2020, vol. 25, # 17]

7
[ 599-89-3 ]
[ 213596-33-9 ]
[ 13021-19-7 ]
[ 58970-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 90 %Chromat. 2: 9 %Chromat.	With potassium phosphate; water; trans-bis(trimethylphosphine)(1-naphthyl)nickel(II) tosylate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;

Reference： [1]Entz, Emily D.; Hooker, Leidy V.; Neufeldt, Sharon R.; Russell, John E. A. [Journal of the American Chemical Society, 2020, vol. 142, # 36, p. 15454 - 15463]

8
[ 106-48-9 ]
[ 13021-19-7 ]
[ 58970-19-7 ]
[ 356031-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / 45 °C / Inert atmosphere 2: Dimethyl(phenyl)phosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Entz, Emily D.; Hooker, Leidy V.; Neufeldt, Sharon R.; Russell, John E. A. [Journal of the American Chemical Society, 2020, vol. 142, # 36, p. 15454 - 15463]

9
[ 106-48-9 ]
[ 13021-19-7 ]
[ 58970-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / 45 °C / Inert atmosphere 2: water; trans-bis(trimethylphosphine)(1-naphthyl)nickel(II) tosylate; potassium phosphate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Entz, Emily D.; Hooker, Leidy V.; Neufeldt, Sharon R.; Russell, John E. A. [Journal of the American Chemical Society, 2020, vol. 142, # 36, p. 15454 - 15463]

10
[ 5720-07-0 ]
[ 13021-19-7 ]
[ 58970-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: magnesium sulfate / tetrahydrofuran / 1 h / 70 °C 2: Dimethyl(phenyl)phosphine; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; potassium phosphate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere; Sealed tube

Reference： [1]Entz, Emily D.; Hooker, Leidy V.; Neufeldt, Sharon R.; Russell, John E. A. [Journal of the American Chemical Society, 2020, vol. 142, # 36, p. 15454 - 15463]

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[ CAS No. 13021-19-7 ] {[proInfo.proName]}

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[ 13021-19-7 ] Synthesis Path-Downstream 1~10

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