[ CAS No. 181058-08-2 ] {[proInfo.proName]}

Name: 181058-08-2|1,3,5-Tris(bromomethyl)-2,4,6-triethylbenzene|95%
Brand: Ambeed
SKU: A471577
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Product Details of [ 181058-08-2 ]

CAS No. :	181058-08-2	MDL No. :	MFCD01076347
Formula :	C₁₅H₂₁Br₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UMKPSDHZXLYFJF-UHFFFAOYSA-N
M.W :	441.04	Pubchem ID :	4589352
Synonyms :

Safety of [ 181058-08-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 181058-08-2 ]

* 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 [ 181058-08-2 ]

[ 181058-08-2 ] Synthesis Path-Downstream 1~36

1
[ 288-13-1 ]
[ 181058-08-2 ]
[ 188883-42-3 ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: The corresponding pyrazole derivative 18, 19 or 22 (4 or 7 equiv) was dissolved in alkaline DMF [containing NaOH (4 or 7 equiv)] and the solution was stirred for 30 min at r.t. The bromomethyl-substituted benzene derivative 21 or 23 (1 equiv) was added and the reaction mixture was stirred for 24-48 h at 70 C. The solution was cooled to r.t., then poured into ice water (50 mL), and the resulting precipitate was collected by filtration, washed thoroughly with H2O (3 × 15 mL) and dried in a desiccator.

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348
[2]Journal of the American Chemical Society,2002,vol. 124,p. 5374 - 5379
[3]Chemical Communications,1997,p. 541 - 542

2
[ 181058-08-2 ]
[ 190779-62-5 ]

Yield	Reaction Conditions	Operation in experiment
92%Spectr.	With sodium azide; at 60℃; for 16h;Inert atmosphere;	Under an inert N2 atmosphere, <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene</strong> 104 (324 mg, 0.74 mmol) was dissolved in anhydrous DMF (4.5 mL) and NaN3 (157 mg, 2.42 mmol) added. The reaction was heated to 60 C for 16 hours. The reaction mixture as then diluted with ethyl acetate (20 mL) and washed with water (3 x 20 mL), dried (MgSO4) and filtered. DMF (4 mL) was added to the filtrate and the solvent removed under vacuum to a volume of -4 mL. Conversion to tris-azide 105 was confirmed by 1H NMR (220 mg, 0.68 mmol, 92%). The resultant DMF solution was transferred to a degassed anhydrous solution of THF (22 mL) and PMe3 (1M in THF, 4.1 mL) under an inert N2 atmosphere. The reaction mixture was stirred at room temperature for1 hour and degassed H20 (5 mL) added, with the reaction mixture stirred for a further 16 hours. The solvent and excess PMe3 was then evaporated by bubbling N2 through the solution, and the crude residue suspended in H20 (-10 mL). The suspension was then freeze dried to afford 106 (148 mg, 0.61 mmol, 90%) as a white solid.

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 7205 - 7213
[2]Chemical Communications,2013,vol. 49,p. 4950 - 4952
[3]Journal of Organic Chemistry,1999,vol. 64,p. 334 - 335
[4]European Journal of Organic Chemistry,2010,p. 6359 - 6365
[5]Journal of Organic Chemistry,2019,vol. 84,p. 840 - 850
[6]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 315 - 323
[7]Zeitschrift fur Naturforschung, B: Chemical Sciences,2013,vol. 68,p. 551 - 556
[8]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 862 - 865
[9]Synthesis,2005,p. 2080 - 2083
[10]Journal of the American Chemical Society,2001,vol. 123,p. 11519 - 11533
[11]Analytical Chemistry,2005,vol. 77,p. 4459 - 4466
[12]European Journal of Organic Chemistry,2013,p. 65 - 76
[13]Patent: WO2018/167503,2018,A1 .Location in patent: Paragraph 00218

3
[ 50-00-0 ]
[ 102-25-0 ]
[ 181058-08-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogen bromide; acetic acid; zinc dibromide; at 90℃; for 16.5h;	In a first step, to a mixture of paraformaldehyde (16.7 g, 556.3 mmol) and triethylbenzene (1, 10 mL, 53.1 mmol) in HBr/AcOH (100 mL, 30 wt %) zinc bromide (19.7 g, 87.5 mmol) was slowly added at room temperature. The mixture was heated to 90 C for 16.5 h, during which time white crystals were formed. The reaction was cooled to room temperature, and the white solid was filtered off, washed with water, and dried under vacuum overnight to give 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene (22.8 g, 51.7 mmol, 97%) as a white solid. In a second step, to a suspension of potassium phthalimide (8.4 g, 45.4 mmol) in dry DMSO (75 mL) 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene (5.0 g, 11.3 mmol) was added at room temperature, under nitrogen atmosphere. The reaction mixture was heated to 84 C for 8 h; the solution obtained was cooled to 0 C, and the formation of a white solid was observed. After 1 h at room temperature, the solid was filtered off, dissolved in water (100 mL), and extracted with CH2Cl2 (2 × 100 mL). The combined organic layers were washed with water (2 × 50 mL), dried over Na2SO4, and concentrated to give 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (4.88 g, 7.63 mmol, 67%) as white crystals. Then the mother liquor was poured into water (200 mL), and the white precipitate formed was filtered off. The solid was dissolved in CH2Cl2 (100 mL), washed with water (3 × 50 mL), and dried over Na2SO4. Evaporation of the organic solvent gave a crude (2.69 g) which was purified by flash column chromatography on silica gel (hexane/EtOAc, 1/1, v/v) to afford a second amount of 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (1.45 g, 2.27 mmol, 20%). In the thrid step, to a suspension of 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (3.2 g, 5.0 mmol) in EtOH/toluene 2:1 v/v (18 mL) hydrazine hydrate (0.98 mL, 30.8 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture was refluxed for 20 h, and during this time a white solid was formed. The reaction was cooled to room temperature, and the white solid was filtered off, dissolved in a 40% aqueous solution of KOH (120 mL), and extracted with CHCl3 (3 × 150 mL). The combined organic layers were washed with water (3 × 150 mL) and dried over Na2SO4. Evaporation of the organic solvent gave 2 (0.973 g, 3.90 mmol, 78%) as a white solid. Mp 138-140 C; 1H NMR (0.1 mol dm-3 in CDCl3, 200 MHz) delta: 3.87 (bs, 6H), 2.82 (q, 6H), 1.26 (bs, 6H), 1.23 (t, 9H). 13C NMR (CDCl3, 50 MHz) delta: 140.3, 137.4, 39.6, 22.5, 16.8.
96%	With hydrogen bromide; acetic acid; zinc dibromide; at 20 - 90℃; for 16.5h;	Add paraformaldehyde (33.5g, 1.11mol) and <strong>[102-25-0]1,3,5-triethylbenzene</strong> (20ml, 106.2mmol) to 100ml of HBr / AcOH (30wt%, mass ratio 3: 7) solution,Slowly add zinc bromide (39.4g, 175mmol) at room temperature,The reaction solution was reacted at 90 C for 16.5 hours.The reaction liquid was cooled to room temperature, and a white solid precipitated, and the solid was filtered out.Wash three times with distilled water and vacuum dry to obtain 45.0g of product, yield 96%,
87%	With hydrogen bromide; zinc dibromide; In acetic acid;	[0057] Compound I was synthesized from commercially available 1,3,5- triethylbenzene. Compounds 5, 6 and 7 were prepared as previously described in Vacca, A. et al, J. Am. Chem. Soc. 2004, 126:16456, Nativi, C. et ah, J. Am. Chem. Soc. 2007, 129:4377 and O'Leary. B.M. et ah, J. Am. Chem. Soc. 2001, 123:11519.[0058] Trimethylester, 8 was prepared by reflupsilonxing 7 in methanol with sulfuric acid as a catalyst. Trihydrazide, 9 was prepared by dissolving the corresponding ester, 8 in ethanol with hydrazine and brief heating under reflux. The final uranyl ligand, Compoundl was prepared from 9 using Kemp's anhydride acid chloride in dry pyridine with DMAP. The uranyl ligand, Compound I was obtained in high purity by subliming off impurities (excess pyridinium chloride).Compound i [0059] Compound I is most soluble in methanol or dimethylsulfoxide, and NMR studies were done in these solvents. Figures 4 and 5 show the H-TSIMR spectra of uranyl- free ligand in MeOD-d4 and 1H-NMR of uranyl ligand in MeOD-d4with uranyl acetate.[0060] The application of Compound I as an agent for uranyl ion sequestration was investigated through liquid-liquid extractions. An aqueous solution of uranyl nitrate (1.6 equivalents) in acetate buffer (pH=5.0) was stirred with chloroform solution of Compound 1 (1 equivalent) and the concentrations of uranium in each phase were determined before and after extraction with Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES). The extraction experiments were run at a series of uranium concentrations: 400 ppm, 40 ppm, and 4 ppm. At 400 ppm, Compound I extracted 55+5% of the aqueous uranyl ion into the organic phase and at 40 ppm 25+5% is extracted. At 4 ppm no uranium was extracted. The uranium can be recovered from the ligand by adding 0.5M HNO3. Compound I is highly selective for uranyl. The extraction of uranyl ion at 400 ppm was also carried out in the presence of six ions that dominate the chemistry of seawater: CT, Na+, Mg+2, Ca+2, K+ and SO4-2. With these ions present at seawater concentrations, Compound I showed no diminished function. Approximately, 55% of the uranyl ion was extracted into the organic phase.

Reference： [1]Synlett,2011,p. 254 - 258
[2]Chemistry - A European Journal,2018,vol. 24,p. 1816 - 1820
[3]Journal of the American Chemical Society,2004,vol. 126,p. 16456 - 16465
[4]Journal of Organic Chemistry,2007,vol. 72,p. 3933 - 3936
[5]Journal of the American Chemical Society,2008,vol. 130,p. 10895 - 10897
[6]Tetrahedron Letters,2012,vol. 53,p. 5110 - 5113
[7]Patent: CN111000804,2020,A .Location in patent: Paragraph 0028-0034
[8]New Journal of Chemistry,2008,vol. 32,p. 1839 - 1842
[9]Journal of Organic Chemistry,2010,vol. 75,p. 6416 - 6423
[10]European Journal of Organic Chemistry,2010,p. 6359 - 6365
[11]Patent: WO2010/138720,2010,A2 .Location in patent: Page/Page column 17-19
[12]Journal of Organic Chemistry,2006,vol. 71,p. 7205 - 7213
[13]Journal of the American Chemical Society,2010,vol. 132,p. 13572 - 13574
[14]Tetrahedron Letters,2014,vol. 55,p. 741 - 744
[15]Synthesis,2005,p. 2080 - 2083
[16]Journal of Chemical Research, Miniprint,1996,p. 1601 - 1618
[17]Journal of Organic Chemistry,1999,vol. 64,p. 334 - 335
[18]Zeitschrift fur Naturforschung, B: Chemical Sciences,2013,vol. 68,p. 551 - 556
[19]Journal of Organic Chemistry,2007,vol. 72,p. 6998 - 7010
[20]Journal of the American Chemical Society,2001,vol. 123,p. 11519 - 11533
[21]European Journal of Organic Chemistry,2010,p. 3858 - 3866
[22]Chinese Chemical Letters,2010,vol. 21,p. 23 - 26
[23]Chinese Journal of Chemistry,2011,vol. 29,p. 1503 - 1510
[24]European Journal of Organic Chemistry,2013,p. 65 - 76
[25]Angewandte Chemie - International Edition,2019,vol. 58,p. 1768 - 1773
Angew. Chem.,2019,p. 1782 - 1787,6
[26]Chemistry - An Asian Journal,2019,vol. 14,p. 1992 - 1999

4
[ 1539-42-0 ]
[ 181058-08-2 ]
[ 223737-62-0 ]

Yield	Reaction Conditions	Operation in experiment
20%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 96h;	1,3,5-Triethyltris(bromomethyl)benzene(1.5 g, 3.39 mmol) in THF (30 mL) was slowly added to anice-chilled solution of dipicolylamine(2.0 g, 11.7 mmol) and triethylamine (3.09 g, 30.6 mmol) in THF (40 mL). After stirring for 5 h at 0C, the reaction solution was allowed to warm to room temperature, and stirring was continued for 4 days. The solvent was removed under reduced pressure, and the residue was treated with aqueous KOH and extracted with CH2Cl2 (3*30 mL). The organic layer was concentrated in vacuo, and the residue solidified upon trituration with diethyl ether. The solid was dissolved in warm toluene and filtered to remove insoluble solids, and the filtrate was evaporated under reduced pressure and again solidified using diethyl ether. This solid was recrystallized from CH3CN to give 2 as a yellow solid (0.54 g, 20%). 1H NMR (600 MHz, CDCl3) delta0.67 (t, 9H, J = 7.2 Hz), 2.87 (q,6H), 3.64 (s, 6H), 3.69 (s, 12H), 7.00 (t, 6H), 7.13 (d, 6H), 7.39 (t, 6H),8.42 (d, 6H); 13C NMR (150 MHz, CDCl3) delta 15.59, 22.08,50.98, 60.10, 121.81, 123.41, 131.93, 136.20, 145.19, 148.56, 159.90.
18%	With triethylamine; In tetrahydrofuran; at 0℃; for 5h;	To an ice-chilled solution of dipicolylamine (2.0 g, 11.7 mmol) and triethylamine (3.09 g, 30.6 mmol) in THF (40 mL), we slowly added 1,3,5-triethyltris(bromomethyl)benzene (1.5 g, 3.39 mmol) in THF (30 mL) at 0C. After being stirred for 5 h at 0C, the reaction solution was then allowed to warm to room temperature and was stirred for 4 days. The solvent was removed under reduced pressure, and the residue was treated with aqueous KOH and extracted with CH2Cl2 (3 &13;&10;&13;&10;12-' coordsize = "1000,1000">30 mL). The organic layer was concentrated in vacuo, and the residue was solidified with diethyl ether. The solid was dissolved in warm toluene and filtered out to remove insoluble solids, and the filtrate was evaporated under reduced pressure and again solidified using diethyl ether. This solid was recrystallized from CH3CN to give a yellow solid 2 (0.49 g, 18%). 1H-NMR (600 MHz, CDCl3) delta 0.67 (t, 9H), 2.87 (q, 6H), 3.64 (s, 6H), 3.69 (s, 12H), 7.00 (t, 6H), 7.13 (d, 6H), 7.39 (t, 6H), 8.42 (d, 6H); 13C-NMR (150 MHz, CDCl3) delta 15.59, 22.08, 50.98, 60.10, 121.81, 123.41, 131.93, 136.20, 145.19, 148.56, 159.90.

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1999,p. 923 - 929
[2]Tetrahedron Letters,2015,vol. 56,p. 5030 - 5033
[3]Tetrahedron Letters,2013,vol. 54,p. 5284 - 5287

5
[ 67-51-6 ]
[ 181058-08-2 ]
1,3,5-tris[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: To the corresponding benzimidazole or pyrazole 16-20 (4.5 or 6.6 equiv), dissolved under N2 atmosphere in anhyd MeCN, NaH (60% dispersion in mineral oil, 4.5 or 6.6 equiv) was added and the mixture was stirred for 30 min at r.t. Then, the bromomethyl-substituted benzene derivative 15, 21 or 23 (1 equiv) was added and the reaction mixture was stirred for up to 5 d at r.t. under N2 atmosphere. The reaction was quenched with H2O (10 mL) and extracted with CHCl3 (3 × 10 mL). The organic layers were combined, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CHCl3-MeOH or CHCl3-MeOH-hexane as the eluent.

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348
[2]Angewandte Chemie - International Edition,1999,vol. 38,p. 2756 - 2759
[3]Journal of the American Chemical Society,2002,vol. 124,p. 5374 - 5379
[4]New Journal of Chemistry,2017,vol. 41,p. 14835 - 14838

6
[ 32405-70-2 ]
[ 181058-08-2 ]
1,3,5-tris(3-(N-ethylamino)pyridiniummethyl)-2,4,6-triethylbenzene bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 9699 - 9715

7
[ 1074-82-4 ]
[ 181058-08-2 ]
[ 828931-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethyl sulfoxide; at 84℃; for 8h;Inert atmosphere;	In a first step, to a mixture of paraformaldehyde (16.7 g, 556.3 mmol) and triethylbenzene (1, 10 mL, 53.1 mmol) in HBr/AcOH (100 mL, 30 wt %) zinc bromide (19.7 g, 87.5 mmol) was slowly added at room temperature. The mixture was heated to 90 C for 16.5 h, during which time white crystals were formed. The reaction was cooled to room temperature, and the white solid was filtered off, washed with water, and dried under vacuum overnight to give <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene</strong> (22.8 g, 51.7 mmol, 97%) as a white solid. In a second step, to a suspension of potassium phthalimide (8.4 g, 45.4 mmol) in dry DMSO (75 mL) <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene</strong> (5.0 g, 11.3 mmol) was added at room temperature, under nitrogen atmosphere. The reaction mixture was heated to 84 C for 8 h; the solution obtained was cooled to 0 C, and the formation of a white solid was observed. After 1 h at room temperature, the solid was filtered off, dissolved in water (100 mL), and extracted with CH2Cl2 (2 × 100 mL). The combined organic layers were washed with water (2 × 50 mL), dried over Na2SO4, and concentrated to give 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (4.88 g, 7.63 mmol, 67%) as white crystals. Then the mother liquor was poured into water (200 mL), and the white precipitate formed was filtered off. The solid was dissolved in CH2Cl2 (100 mL), washed with water (3 × 50 mL), and dried over Na2SO4. Evaporation of the organic solvent gave a crude (2.69 g) which was purified by flash column chromatography on silica gel (hexane/EtOAc, 1/1, v/v) to afford a second amount of 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (1.45 g, 2.27 mmol, 20%). In the thrid step, to a suspension of 1,3,5-tris(phthalimidomethyl)-2,4,6-triethylbenzene (3.2 g, 5.0 mmol) in EtOH/toluene 2:1 v/v (18 mL) hydrazine hydrate (0.98 mL, 30.8 mmol) was added at room temperature under nitrogen atmosphere. The reaction mixture was refluxed for 20 h, and during this time a white solid was formed. The reaction was cooled to room temperature, and the white solid was filtered off, dissolved in a 40% aqueous solution of KOH (120 mL), and extracted with CHCl3 (3 × 150 mL). The combined organic layers were washed with water (3 × 150 mL) and dried over Na2SO4. Evaporation of the organic solvent gave 2 (0.973 g, 3.90 mmol, 78%) as a white solid. Mp 138-140 C; 1H NMR (0.1 mol dm-3 in CDCl3, 200 MHz) delta: 3.87 (bs, 6H), 2.82 (q, 6H), 1.26 (bs, 6H), 1.23 (t, 9H). 13C NMR (CDCl3, 50 MHz) delta: 140.3, 137.4, 39.6, 22.5, 16.8.

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2319 - 2326
[2]Journal of the American Chemical Society,2004,vol. 126,p. 16456 - 16465
[3]Chemistry - A European Journal,2018,vol. 24,p. 1816 - 1820
[4]European Journal of Organic Chemistry,2010,p. 458 - 463
[5]Tetrahedron Letters,2012,vol. 53,p. 5110 - 5113

8
[ 141-86-6 ]
[ 181058-08-2 ]
[ 797818-02-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate; In acetonitrile; at 20℃; for 26h;Heating / reflux;	1,3,5-Tris[(6-amino-pyridin-2-yl)aminomethyl]-2,4,6-triethylbenzene (2b): A mixture of <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethyl-benzene</strong> (0.79 g, 1.8 mmol), 2,6-diamino-pyridine (1.20 g, 11 mmol), and K2CO3 (0.79 g) in CH3CN (100 mL) was stirred at room temperature for 24 h and then heated under reflux for 2 h. After filtration of the reaction mixture and evaporation of CH3CN, the obtained powder was suspended in CHCl3. The suspension was filtrated, the chloroform solution was washed several times with water, dried, and the solvent was removed under reduced pressure. The crude product was crystallized from THF/hexane. Yield 40%. M.p. 164-165 C; 1H NMR (500 MHz, CDCl3): delta = 1.22 (t, 9H, J = 7.5 Hz), 2.75 (q, 6H, J = 7.5 Hz), 4.05 (t, 3H, J = 4.2 Hz), 4.20 (s, 6H), 4.35 (d, 6H, J = 4.2 Hz), 5.83-5.86 (m, 6H), 7.24 (m, 3H); 13C NMR (125 MHz, CDCl3): delta = 16.9, 23.0, 40.6, 95.9, 96.9, 133.3, 139.4, 143.8, 157.8, 157.9; HR-MS calcd for C30H39N9: 525.3328; found: 525.3322. Rf = 0.21 (CHCl3/CH3OH 7:1 v/v).

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 7448 - 7462
[2]European Journal of Organic Chemistry,2007,p. 3633 - 3638
[3]Patent: EP1972627,2008,A1 .Location in patent: Page/Page column 9

9
[ 5407-87-4 ]
[ 181058-08-2 ]
1-(bromomethyl)-3,5-bis[((4,6-dimethylpyridin-2-yl)amino)-methyl]-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate; In tetrahydrofuran; acetonitrile; at 20℃; for 72h;	Compound 22. To a mixture of 1,3,5-tris(bromomethyl)-2,4,6-trimethyl-benzene (1b) (3.00 g, 6.80 mmol) and K2CO3 (1.88 g, 13.60 mmol) in CH3CN/THF (1:1 v/v; 40 mL) was added dropwise a CH3CN (10 mL) solution of 2-amino-4,6-dimethyl-pyridine (1.66 g, 13.60 mmol).The mixture was stirred at room temperature for 72 h. After filtration and evaporation of solvents, the crude product was purified by column chromatography (ethyl acetate/toluene, 1:3 v/v). Yield 30 %. M.p. 77-78 C. 1H-NMR (400 MHz, CDCl3) delta = 1.22 (t, 3H, J = 7.5 Hz), 1.29 (t, 6H, J = 7.5 Hz), 2.24 (s, 6H), 2.36 (s, 6 H), 2.73 (q, 2H, J = 7.5 Hz), 2.85 (q, 4H, J = 7.5 Hz), 4.23 (t, 2H, J = 4.2 Hz), 4.37 (d, 4H, J = 4.2 Hz), 4.62 (s, 2 H), 6.10 (s, 2 H), 6.35 (s, 2 H). 13C-NMR (100 MHz, CDCl3) delta = 16.4, 16.7, 21.1, 22.8, 23.0, 24.1, 29.6, 40.5, 103.6, 113.9, 131.9, 133.4, 143.8, 144.9, 148.9, 156.5, 158.0. HR-MS calcd for C29H39BrN4 5232.2353; found: 522.2360. Rf= 0.31 (ethyl acetate/toluene, 1:3 v/v).
30%	With potassium carbonate; In tetrahydrofuran; acetonitrile; at 20℃; for 72h;	To a mixture of 1,3,5-tris(bromomethyl)-2,4,6-trimethyl-benzene (1b) (3.00 g, 6.80 mmol) and K2CO3 (1.88 g, 13.60 mmol) in CH3CN/THF (1:1 v/v; 40 mL) was added dropwise a CH3CN (10 mL) solution of 2-aminor4,6-dimethyl-pyridine (1.66 g, 13.60 mmol).The mixture was stirred at room temperature for 72 h. After filtration and evaporation of solvents, the crude product was purified by column chromatography (ethyl acetate/toluene, 1:3 v/v). Yield 30 %. M.p. 77-78 C. 1H-NMR (400 MHz, CDCl3) delta = 1.22 (t, 3H, J = 7.5 Hz), 1.29 (t, 6H, J = 7.5 Hz), 2.24 (s, 6H), 2.36 (s, 6 H), 2.73 (q, 2H, J = 7.5 Hz), 2.85 (q, 4H, J = 7.5 Hz), 4.23 (t, 2H, J = 4.2 Hz), 4.37 (d, 4H, J = 4.2 Hz), 4.62 (s, 2 H), 6.10 (s, 2 H), 6.35 (s, 2 H). 13C-NMR (100 MHz, CDCl3) delta= 16.4, 16.7, 21.1, 22.8, 23.0, 24.1, 29.6, 40.5, 103.6, 113.9, 131.9, 133.4, 143.8, 144.9, 148.9, 156.5, 158.0. HR-MS calcd for C29H39BrN4 5232.2353; found: 522.2360. Rf= 0.31 (ethyl acetate/toluene, 1:3 v/v).

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[2]Patent: EP1972627,2008,A1 .Location in patent: Page/Page column 10
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[5]Patent: EP1972338,2008,A1 .Location in patent: Page/Page column 12
[6]Journal of Organic Chemistry,2008,vol. 73,p. 7444 - 7450
[7]Journal of Organic Chemistry,2013,vol. 78,p. 9013 - 9020

10
[ 181058-08-2 ]
[ 906565-55-7 ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 1816 - 1820
[2]Chemistry - A European Journal,2010,vol. 16,p. 414 - 418
[3]Chemical Communications,2013,vol. 49,p. 6379 - 6381
[4]European Journal of Organic Chemistry,2010,p. 3858 - 3866
[5]Chemistry - A European Journal,2011,vol. 17,p. 4814 - 4820

11
[ 61275-22-7 ]
[ 181058-08-2 ]
[ 1228316-05-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3878 - 3881

12
[ 181058-08-2 ]
[ 181058-09-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium cyanide; In dimethyl sulfoxide; at 20℃; for 24h;	[0057] Compound I was synthesized from commercially available 1,3,5- triethylbenzene. Compounds 5, 6 and 7 were prepared as previously described in Vacca, A. et al, J. Am. Chem. Soc. 2004, 126:16456, Nativi, C. et ah, J. Am. Chem. Soc. 2007, 129:4377 and O'Leary. B.M. et ah, J. Am. Chem. Soc. 2001, 123:11519.[0058] Trimethylester, 8 was prepared by reflupsilonxing 7 in methanol with sulfuric acid as a catalyst. Trihydrazide, 9 was prepared by dissolving the corresponding ester, 8 in ethanol with hydrazine and brief heating under reflux. The final uranyl ligand, Compoundl was prepared from 9 using Kemp's anhydride acid chloride in dry pyridine with DMAP. The uranyl ligand, Compound I was obtained in high purity by subliming off impurities (excess pyridinium chloride).Compound i [0059] Compound I is most soluble in methanol or dimethylsulfoxide, and NMR studies were done in these solvents. Figures 4 and 5 show the H-TSIMR spectra of uranyl- free ligand in MeOD-d4 and 1H-NMR of uranyl ligand in MeOD-d4with uranyl acetate.[0060] The application of Compound I as an agent for uranyl ion sequestration was investigated through liquid-liquid extractions. An aqueous solution of uranyl nitrate (1.6 equivalents) in acetate buffer (pH=5.0) was stirred with chloroform solution of Compound 1 (1 equivalent) and the concentrations of uranium in each phase were determined before and after extraction with Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP-AES). The extraction experiments were run at a series of uranium concentrations: 400 ppm, 40 ppm, and 4 ppm. At 400 ppm, Compound I extracted 55+5% of the aqueous uranyl ion into the organic phase and at 40 ppm 25+5% is extracted. At 4 ppm no uranium was extracted. The uranium can be recovered from the ligand by adding 0.5M HNO3. Compound I is highly selective for uranyl. The extraction of uranyl ion at 400 ppm was also carried out in the presence of six ions that dominate the chemistry of seawater: CT, Na+, Mg+2, Ca+2, K+ and SO4-2. With these ions present at seawater concentrations, Compound I showed no diminished function. Approximately, 55% of the uranyl ion was extracted into the organic phase.

Reference： [1]Patent: WO2010/138720,2010,A2 .Location in patent: Page/Page column 17-19

13
[ 181058-08-2 ]
[ 45676-04-8 ]
1,3,5-{tris(3-tert-butylimidazolium)methyl}-2,4,6-triethylbenzene tribromide [ No CAS ]

Reference： [1]Organometallics,2010,vol. 29,p. 4097 - 4104

14
[ 181058-08-2 ]
[ 220472-99-1 ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 840 - 850
[2]Synlett,2011,p. 254 - 258
[3]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3186 - 3195
[4]European Journal of Inorganic Chemistry,2013,p. 3412 - 3420
[5]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 199 - 203

15
[ 51-17-2 ]
[ 181058-08-2 ]
[ 1309136-56-8 ]

Yield	Reaction Conditions	Operation in experiment
90%		General procedure: To the corresponding benzimidazole or pyrazole 16-20 (4.5 or 6.6 equiv), dissolved under N2 atmosphere in anhyd MeCN, NaH (60% dispersion in mineral oil, 4.5 or 6.6 equiv) was added and the mixture was stirred for 30 min at r.t. Then, the bromomethyl-substituted benzene derivative 15, 21 or 23 (1 equiv) was added and the reaction mixture was stirred for up to 5 d at r.t. under N2 atmosphere. The reaction was quenched with H2O (10 mL) and extracted with CHCl3 (3 × 10 mL). The organic layers were combined, dried over MgSO4 and filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using CHCl3-MeOH or CHCl3-MeOH-hexane as the eluent.

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348
[2]Organic Letters,2011,vol. 13,p. 3024 - 3027
[3]Chemistry - An Asian Journal,2019,vol. 14,p. 1992 - 1999

16
[ 90-02-8 ]
[ 181058-08-2 ]
[ 1338326-00-3 ]

Yield	Reaction Conditions	Operation in experiment
64%		A solution of salicylaldehyde (111 mg, 0.91 mmol) and KOH (59 mg, 1.02 mmol) in nPrOH (20 mL) was stirred vigorously at room temperature. After 30 min <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene</strong> (100 mg, 0.23 mmol) was added. The reaction mixture was heated to reflux for 11 h. After evaporation of the solvent, the residue was dissolved in CH2Cl2 and then washed with water. Adding MeOH to the solution yielded a precipitated solid in 64% yield (83 mg): light brown solid; mp: 190-192 C; IR numax: 3477, 2967, 2873, 1687, 1598, 1484, 1228 cm-1; 1H NMR (400 MHz, CDCl3): delta 1.23 (t, 9H, -CH3, J = 7.6 Hz), 2.85 (q, 6H, -CH2, J = 7.6 Hz), 5.21 (s, 6H, -CH2), 7.07-7.10 (m, 3H, Ar), 7.22-7.24 (m, 3H, Ar), 7.60-7.65 (m, 3H, Ar), 7.86-7.88 (m, 3H, Ar), 10.40 (s, 3H, -CHO); 13C NMR (100 MHz, CDCl3): delta 16.8, 23.3, 65.0, 112.6, 121.4, 125.3, 128.7, 130.5, 136.3, 147.1, 161.3, 189.8; MS (ESI) m/z (%): 564 (M+, 100). Anal. Calcd for C36H36O6: C, 76.57; H, 6.43. Found: C, 76.48; H, 6.52.

Reference： [1]Chinese Journal of Chemistry,2011,vol. 29,p. 1503 - 1510
[2]Tetrahedron Letters,2011,vol. 52,p. 3886 - 3890

17
[ 18638-99-8 ]
[ 181058-08-2 ]
[ 1314875-80-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With triethylamine; In dichloromethane; at 20℃;	EXAMPLE 9: Synthesis of 1,3,5-Tris(3,4,5-trimethoxybenzylaminomethyl)-2,4,6- triethylbenzene (18, AL 177). A solution of 11 (167 mg, 0.37 mmol) and the commercially available 3,4,5-trimethoxybenzylamine 14 (262 mg, 1.3 mmol) was treated according to the general procedure B. The residue was purified by CCTLC (dichloromethane/methanol/NH4OH, 9:1 :0.2) to give 0.19 g (65%) of 18, AL 177 as a white solid: mp 100-102 C. HPLC: fow = 2.78. 1H NMR (CDCI3, 300 MHz) delta: 1.11 (t, J = 7.4 Hz, 9H, CH3-CH2), 2.71 (q, , J = 7.4 Hz, 6H CH3- CH2), 3.83 (s, 6H, CH2-NH), 3.87 (bs, 6H, CH3-O and CH2-NH), 6.64 (s, 6H, H-Ar). MS (ES+) m/z: 791 (M+H)+.

Reference： [1]Patent: WO2011/85454,2011,A1 .Location in patent: Page/Page column 36; 39

18
[ 302-95-4 ]
[ 181058-08-2 ]
[ 1359731-67-1 ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 321 - 329

19
[ 33941-15-0 ]
[ 181058-08-2 ]
[ 1415606-97-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium carbonate; In acetonitrile; at 20℃; for 24h;Inert atmosphere; Reflux;	A mixture of 3 (1.00 g, 2.27 mmol), 1-aza-18-crown-6 (1.84 g, 6.99 mmol) and sodium carbonate (2.94 g, 27.7 mmol) in dry acetonitrile (15 mL) was stirred at room temperature under an atmosphere of nitrogen for 20 h. The mixture was then heated at reflux for 4 h. After cooling, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (9:1 v/v chloroform/methanol elution), to give 11 (2.08 g, 93%) as a pale yellow oil. Found: (M+H)+, 988.6680. C51H94N3O15 requires 988.6685; found: C, 58.7; H, 9.2; N, 4.0. C51H93N3O15.3H2O requires C, 58.8; H, 9.6; N, 4.0%; 1H NMR (300 MHz, CD3OD) delta 3.70-3.52 (complex m, 66H), 3.10 (q, J=7.3 Hz, 6H) 2.75 (t, J=5.5 Hz, 12H), 1.09 (t, J=7.3 Hz, 9H); 13C NMR (75.5 MHz, CD3OD) delta 146.1 (C), 133.3 (C), 71.9 (CH2), 71.75 (CH2), 71.71 (CH2), 71.4 (CH2), 54.8 (CH2), 53.8 (NCH2), 23.2 (CH2), 16.5 (CH3), one signal overlapping; IR numax (NaCl)/cm-1 3459 (s), 2867 (s), 1117 (s); MS (ESI) m/z 991 [(M+H)+, 15%] 990 (100) 726 (5), 462 (3).

Reference： [1]Tetrahedron,2013,vol. 69,p. 38 - 42

20
[ 181058-08-2 ]
[ 66943-05-3 ]
[ 1415606-96-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate; In acetonitrile; at 20℃; for 24h;Inert atmosphere; Reflux;	A mixture of 3 (1.10 g, 2.5 mmol), 1-aza-15-crown-5 (1.76 g, 8.03 mmol) and sodium carbonate (2.94 mg, 21 mmol) in dry acetonitrile (15 mL) was stirred at room temperature under an atmosphere of nitrogen for 20 h. The mixture was then heated at reflux for 4 h. After cooling, the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (9:1 v/v chloroform/methanol elution), to give 10 (2.03 g, 95%) as a yellow oil. Found: (M+H)+, 856.5894. C45H82N3O12 requires 856.5899; found: C, 62.2; H, 9.6; N, 4.7. C45H81N3O12·0.5H2O requires C, 62.5; H, 9.55; N, 4.9%; 1H NMR (300 MHz, CD3OD) delta 3.76-3.51 (complex m, 54H), 3.10 (q, J=7.3 Hz, 6H) 2.75 (t, J=5.5 Hz, 12H), 1.09 (t, J=7.3 Hz, 9H); 13C NMR (75.5 MHz, CD3OD) delta 146.2 (C), 133.3 (C), 71.9 (CH2), 71.4 (CH2, overlapped), 71.1 (CH2), 55.2 (CH2), 54.3 (CH2), 23.2 (CH2), 16.4 (CH3); IR numax (NaCl)/cm-1 3481 (m), 2865 (s), 1126 (s); MS (ESI) m/z 857 [(M+H)+, 35%] 856 (100) 637 (10), 418 (4).

Reference： [1]Tetrahedron,2013,vol. 69,p. 38 - 42

21
C₁₄H₁₇NS₆ [ No CAS ]
[ 181058-08-2 ]
C₅₇H₆₉N₃S₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 3h;Inert atmosphere; Cooling with ice;	General procedure: Pyrrolo-TTF 2 and tribromide 3 were suspendedin abs. DMF (5 mL) and degassed using freeze-pump-thaw method. After that the reactionmixture was cooled with an ice bath, and NaH was added. The mixture was allowed to warm toRT and stirred for additional 3 h, whereupon the color darkened. Then the mixture was carefullypoured into ca. 100 mL of brine and extracted with CH2Cl2 (3×30 mL). The organic phase wasdried (Na2SO4) and evaporated to dryness. The crude product was purified by flashchromatography (CH2Cl2/cyclohexane, 2:3).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 741 - 744

22
[ 753478-52-3 ]
[ 181058-08-2 ]
[ 1538607-67-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20℃; for 3h;Inert atmosphere; Cooling with ice;	General procedure: Pyrrolo-TTF 2 and tribromide 3 were suspendedin abs. DMF (5 mL) and degassed using freeze-pump-thaw method. After that the reactionmixture was cooled with an ice bath, and NaH was added. The mixture was allowed to warm toRT and stirred for additional 3 h, whereupon the color darkened. Then the mixture was carefullypoured into ca. 100 mL of brine and extracted with CH2Cl2 (3×30 mL). The organic phase wasdried (Na2SO4) and evaporated to dryness. The crude product was purified by flashchromatography (CH2Cl2/cyclohexane, 2:3).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 741 - 744

23
[ 181058-08-2 ]
[ 54624-57-6 ]
[ 1570129-34-8 ]

Yield	Reaction Conditions	Operation in experiment
77%		To <strong>[54624-57-6]<strong>[54624-57-6]2-bromo-1H-benzimidazol</strong>e</strong> (16; 1.47 g, 7.48 mmol), dissolvedin THF?MeCN (4:1, 20 mL), DIPEA (1.27 mL, 7.48 mmol) wasadded and the mixture was stirred for 1 h at r.t. Then, compound 21(1 g, 2.27 mmol) was added and the reaction mixture was stirred for7 d at r.t. The resulting precipitate was collected by filtration,

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348

24
[ 2075-45-8 ]
[ 181058-08-2 ]
[ 1570129-37-1 ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: The corresponding pyrazole derivative 18, 19 or 22 (4 or 7 equiv) was dissolved in alkaline DMF [containing NaOH (4 or 7 equiv)] and the solution was stirred for 30 min at r.t. The bromomethyl-substituted benzene derivative 21 or 23 (1 equiv) was added and the reaction mixture was stirred for 24-48 h at 70 C. The solution was cooled to r.t., then poured into ice water (50 mL), and the resulting precipitate was collected by filtration, washed thoroughly with H2O (3 × 15 mL) and dried in a desiccator.

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348

25
[ 3398-16-1 ]
[ 181058-08-2 ]
[ 436084-62-7 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: The corresponding pyrazole derivative 18, 19 or 22 (4 or 7 equiv) was dissolved in alkaline DMF [containing NaOH (4 or 7 equiv)] and the solution was stirred for 30 min at r.t. The bromomethyl-substituted benzene derivative 21 or 23 (1 equiv) was added and the reaction mixture was stirred for 24-48 h at 70 C. The solution was cooled to r.t., then poured into ice water (50 mL), and the resulting precipitate was collected by filtration, washed thoroughly with H2O (3 × 15 mL) and dried in a desiccator.

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348

26
[ 51-17-2 ]
[ 181058-08-2 ]
C₅₁H₅₇N₆⁽³⁺⁾*3Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		To 1H-benzimidazole (17; 442 mg, 3.74 mmol), dissolved in THF-MeCN (4:1, 15 mL), DIPEA (0.64 mL, 3.74 mmol) was added and the mixture was stirred for 1 h at r.t. Then, compound 21 (500 mg, 1.13 mmol) was added and the reaction mixture was stirred for 48 h at r.t. The resulting precipitate was collected by filtration, washed thoroughly with THF and dried in vacuo. Compound 14a was obtained as a white solid

Reference： [1]Synthesis,2013,vol. 45,p. 3341 - 3348

27
[ 181058-08-2 ]
[ 612833-37-1 ]
1,3,5-tris(2-methoxy-5-cyanophenylmethyl)-2,4,6-triethylbenzene [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 12920 - 12923

28
[ 2227-29-4 ]
[ 181058-08-2 ]
1,3,5-tris(diisopropylhydrosilylmethyl)-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45.7%	With magnesium; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; Cooling with ice;	To a solution of diisopropylchlorosilane (3.70mL, 21.7mmol) in anhydrous THF (10mL) and magnesium (0.559g, 23.0mmol), <strong>[181058-08-2]1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene</strong> (1c) (3.00g, 6.80mmol) in anhydrous THF (40mL) was added dropwise over 1h cooling in a salt-ice bath. The resulting mixture was stirred for 3h at room temperature, then quenched with saturated NH4Cl aqueous solution and extracted with CHCl3. After the organic layer was dried over MgSO4, the solvent was evaporated. The crude product was purified by silica gel column with hexane as the eluent and recrystallized with hot methanol to yield 1.70g of 2c (45.7%) as a white solid. (0028) For 2c: m.p. 65C; 1H-NMR (500MHz, CDCl3): delta 3.58 (m, 3H), 2.61 (q, J=7.3Hz, 6H), 2.14 (d, J=4.1Hz, 6H), 1.14 (t, J=7.3Hz, 9H), 1.03 (d, J=6.4Hz, 18H), 1.01-0.92 (m, 6H), 0.91 (d, J=6.4Hz, 18H); 13C-NMR (125MHz, CDCl3): delta 135.09, 133.60, 24.13, 19.17, 18.95, 13.60, 12.33, 10.86; HRMS (ESI): calcd for C33H67Si3 ([M+H]+): 547.4551, found: 547.4513; IR (KBr): =2938 (s), 2864 (s), 2095 (s, Si-H), 1558 (vw), 1463 (m), 1413 (w), 1380 (w), 1240 (w), 1170 (m), 1074 (w), 1004 (m), 877 (s), 795 (s), 725 (m), 691 (m), 647 (w)cm-1.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 799-800,p. 265 - 272
[2]Chemical Communications,2015,vol. 51,p. 14746 - 14749

29
[ 1314875-82-5 ]
[ 181058-08-2 ]
[ 1314875-83-6 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine; In dichloromethane; at 30℃;	To a solution of the tris bromo derivative 18 [7] (50 mg,0.11 mmol) in dichloromethane (1 mL) the aminoethyl derivative 15(231 mg, 0.47 mmol) and Et3N (65 ml, 0.47 mmol) were added. Thereaction mixture was stirred at 30 C overnight, diluted withdichloromethane (15 mL) and washed with brine (3 15 mL). Theorganic phase was dried over anhydrous MgSO4, filtered, andevaporated to dryness. The residue was purified by CCTLC usingdichloromethane:methanol:ammonia (15:1:0.4) as eluent to yield106 mg (57%) of 19 as a colorless oil.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 106,p. 132 - 143

30
N-(4-aminobutyl)-2,3,4-tris(benzyloxy)benzamide [ No CAS ]
[ 181058-08-2 ]
1,3,5-tris(2,3,4-tribenzyloxybenzamidobutylaminomethyl)-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With triethylamine; In dichloromethane; at 20℃; for 2h;	To a solution of the tris bromo derivative 18 [7] (29 mg,0.07 mmol) in dichloromethane (0.5 mL), the aminobutyl derivative16 (133 mg, 0.26 mmol) and triethylamine were added (36 ml,0.47 mmol). The reaction mixture was stirred at room temperaturefor 2 h, diluted with dichloromethane (15 mL) and washed withbrine (3 15 mL). The organic phase was dried over anhydrousMgSO4, filtered, and evaporated. The residue was purified by CCTLCusing dichloromethane:methanol (10:1) as eluent to yield 51 mg(46%) of 21 as a yellow oil.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 106,p. 132 - 143

31
piperazin-1-yl-(2,3,4-tris(benzyloxy)phenyl)methanone [ No CAS ]
[ 181058-08-2 ]
1,3,5-tris[(4-(2,3,4-tribenzyloxyphenylcarbonyl)piperazin-1-yl)methyl]-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine; In dichloromethane; at 20℃;	To a solution of the tris bromo derivative 18 [7] (43 mg,0.10 mmol) in dichloromethane (1 mL), the piperazinyl derivative17 (198 mg, 0.39 mmol) and Et3N were added (54 ml, 0.39 mmol).The reaction mixture was stirred at room temperature overnight,diluted with dichloromethane (15 mL) and washed with brine(3 15 mL). The organic phase was dried over anhydrous MgSO4,filtered, and evaporated. The residue was purified by CCTLC usingdichloromethane:methanol (30:1) to yield 127 mg (75%) of 23 as ayellow oil.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 106,p. 132 - 143

32
C₁₀H₂₃N₃ [ No CAS ]
[ 181058-08-2 ]
C₄₅H₉₃N₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium carbonate; In toluene; at 75℃; for 72h;Inert atmosphere;	A suspension of 2,4,6-ethyl-1,3,5-tris-benzyl bromide (1.00?g, 2.50?mmol), potassium carbonate (1.73?g, 12.5?mmol) and 3,3'-iminobis(N,N-dimethylpropylamine) (4.68?g, 25.0?mmol) in dry toluene (10?ml) was heated in an oil bath at 75?C for 72 h under a nitrogen atmosphere. The mixture was then cooled to room temperature, filtered through Celite and washed with toluene (10?ml). The filtrate was concentrated in vacuo and redissolved in ethylacetate, followed by extraction of the organic phase with water. In addition the organic phase was dried over sodium sulfate and concentrated in vacuum to provide tateb as a light yellow oil which slowly solidified upon standing at room temperature (776?mg, 41%). 1H NMR (300?MHz, CDCl3): delta ppm 3.54 (6H, s), 2.39 (12H, m), 2.12 (54H, m), 1.56 (12, q) and 1.07 (9H, t). ESI-MS (+ve; m/z): 760.77 [L?+?H]+

Reference： [1]Inorganica Chimica Acta,2018,vol. 481,p. 159 - 165

33
[ 354-38-1 ]
[ 181058-08-2 ]
[ 1137672-92-4 ]

Yield	Reaction Conditions	Operation in experiment
93%		NaH (3.809 g, 0.095 mol, 60% in mineral oil) was added to a Schlenk flask (100 mL) and placed under nitrogen. The mineral oil was removed by washing the solids with 3x 25 mL petroleum ether 60-80 C. The washed NaH was suspended in anhydrous DMF (40 mL) and vigorously stirred for Ca. 10 mins whilst cooling in an ice bath. Solid <strong>[354-38-1]trifluoroacetamide</strong> (16.147 g, 0.143 mol) was added portion-wise under a nitrogen counter-flow. After five minutes of stirring the mixture was let warm to room temperature. Once the evolution of gas had completely stopped (within 1 hour), solid 1,3,5tribromomethyl2,4,6trimethoxylbenzene* (7.00 g, 0.016 mol) was added portion-wise under a nitrogen counter-flow and the resulting white suspension was stirred at room temperature. After ca. 18 hours, the suspension was poured into 0.5 M HCI (150 mL) and the light orange precipitate collected on a frit. The solids were washed with water (2 x 10 mL) and then dried under vacuum overnight (ca. 102 mbar). Off-white solid (7.910 g, 0.015 mol 93 %). The intermediate acetamide (4.90 g, 0.009 mol) was dissolved in methanol (38.6 mL) and water (38.6 mL). NaOH (1.05 g, 3.150 mol) was added and the reaction mixture was left to stir for Ca. 18 hours at 65 C. Solid Boc2O (7.287 g, 0.033 mol) and triethylamine (2.534 mL, 0.026 mol) were added and the reaction was left to stir for a further 4 hours at ambient temperature. The reaction mixture was diluted with DCM (200 mL) and washed with sat. aq. NaHCO3 (200 mL), 1 M NaOH (200 mL) and brine (100 mL). The organic phase was concentrated to dryness and the resultant crude product purified by MPLC (0-*50% MeOH in DCM). Colourless solid (4.820 g, 0.009 mcI, 96 %).

Reference： [1]Patent: WO2018/167503,2018,A1 .Location in patent: Paragraph 00243

34
[ 10199-68-5 ]
[ 181058-08-2 ]
C₄₂H₄₂N₆ [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 7251 - 7258

35
[ 114474-26-9 ]
[ 181058-08-2 ]
C₄₂H₃₉N₉O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 4-(4-nitrophenyl)-1H-pyrazole With sodium hydroxide In N,N-dimethyl-formamide for 0.666667h; Stage #2: 1,3,5-tris(bromomethyl)-2,4,6-triethylbenzene In N,N-dimethyl-formamide at 70℃; for 36h;

Reference： [1]Kandel, Shambhu; Sathish, Veerasamy; Mathivathanan, Logesh; Morozov, Alexander N.; Mebel, Alexander M.; Raptis, Raphael G. [New Journal of Chemistry, 2019, vol. 43, # 19, p. 7251 - 7258]

36
[ 148-24-3 ]
[ 181058-08-2 ]
1,3,5-tris-(8-methoxyquinolin)-2,4,6-triethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In tetrahydrofuran at 80℃; for 48h;	1, 3, 5-tris-((8-methoxyquinolin)-2, 4, 6-triethylbenzene (L¹) 1, 3, 5-Tris(bromomethyl)-2, 4, 6-triethylbenzene (1.50 g, 3.4 mmol), quinolin-8-ol (1.58 g, 10.9 mmol) and potassium carbonate (3.45 g, 20.4 mmol) were added into a bottle flask and then refluxed in THF (80 mL) at 80 for 48 h. Then the residue was washed with water and extracted with dichloromethane. The extract solution was dried over anhydrous Na2SO4 and the solvent was distilled under a vacuum condition. Next, chromatography on silica gel elution with dichloromethane/methanol (v/v, 30:1) afforded the pure product L1 as white solid (1.83 g, 2.89 mmol) in 85% yield. 1H NMR (298K, 400 MHz, DMSO-d6) δ 8.83-8.82 (m, 1H), 8.32-8.30 (m, 1H), 7.60 - 7.51 (m, 4H), 5.36 (s, 2H), 2.91-2.87 (m, 2H), 1.24 (t, J = 7.5 Hz, 3H). 1H NMR (233K, 500 MHz, Chloroform-d) δ 8.92 (s, 1H), 8.14 (d, J = 8.3 Hz, 1H), 7.54 (t, J = 8.0 Hz, 1H), 7.43 (dd, J = 8.8, 4.5 Hz, 2H), 7.32 (d, J = 7.8 Hz, 1H), 5.28 (s, 1H), 2.90 - 2.86 (m, 1H). 13C NMR (100 MHz, Chloroform-d) δ 155.31, 149.23, 147.06, 140.69, 135.71, 130.80, 129.56, 126.70, 121.55, 119.97, 109.62, 65.71, 23.49, 16.68. HR-ESI-MS: [L1+H]+, calcd for C42H40N3O3+, 634.3, found, 634.3[L1+Na]+, calcd for C42H39N3O3Na+, 656.3, found, 656.3; [L1+K]+, calcd for C42H39N3O3K+, 672.3, found, 672.3. IR(KBr, ν/cm-1): 2960 (Ar-H),1630(C=N), 1503(C=C),1096(Ar-O), 689(C-H).

Reference： [1]Dong, Geng; Jiang, Xuan-Feng; Shang, Ping [Inorganica Chimica Acta, 2022, vol. 530]

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[ 181058-08-2 ] Synthesis Path-Downstream 1~36

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[ 181058-08-2 ]