[ CAS No. 15442-91-8 ]

Name: 15442-91-8|1,2,4,5-Tetrakis(bromomethyl)benzene|95%
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Quality Control of [ 15442-91-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 15442-91-8 ]

CAS No. :	15442-91-8	MDL No. :	MFCD00009664
Formula :	C₁₀H₁₀Br₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UTXIKCCNBUIWPT-UHFFFAOYSA-N
M.W :	449.80 g/mol	Pubchem ID :	284971
Synonyms :

Calculated chemistry of [ 15442-91-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.79
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.13
Log Po/w (XLOGP3) :	4.16
Log Po/w (WLOGP) :	4.66
Log Po/w (MLOGP) :	5.18
Log Po/w (SILICOS-IT) :	5.9
Consensus Log Po/w :	4.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.3
Solubility :	0.00224 mg/ml ; 0.00000498 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.87
Solubility :	0.061 mg/ml ; 0.000136 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-7.3
Solubility :	0.0000225 mg/ml ; 0.0000000501 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.06

Safety of [ 15442-91-8 ]

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 [ 15442-91-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 15442-91-8 ]
Downstream synthetic route of [ 15442-91-8 ]

[ 15442-91-8 ] Synthesis Path-Upstream 1~3

1
[ 95-93-2 ]
[ 15442-91-8 ]

Yield	Reaction Conditions	Operation in experiment
15%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 77℃; for 0.833333 h;	1,2,4,5-tetrakis(bromomethyl)benzene (1c) was obtained by the reaction of 1,2,4,5-tetramethylbenzene(2.8 g; 20 mmol) with NBS (14.4 g; 80 mmol) and benzoyl peroxide (1 g; 5.9 mmol) in tetrachloromethane(50 mL). Reagents were heated at 77 °C for 50 min. The precipitate was filtered off under reducedpressure and washed with hot tetrachloromethane. The filtrate was concentrated to small volume andcooled to 4 °C. Crude product was filtrated and purified by crystallization from methanol. Rt< 1 h,white solid (15percent), m.p. 159–160 °C. 1H-NMR (CDCl3) δ: 7.37 ppm (2H, a), 4.60 ppm (8H, b). 13C-NMR(CDCl3) : 137.6 ppm (a), 133.6 ppm (h), 28.7 ppm (b). FT-IR (KBr) νmax: 3026, 2980, 2933, 1504, 1456,1210, 911, 797, 678, 598.

Reference： [1] Journal of the Chinese Chemical Society, 2002, vol. 49, # 1, p. 77 - 82
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 26, p. 4281 - 4286
[3] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 247, p. 23 - 30
[4] Heterocycles, 2015, vol. 90, # 1, p. 645 - 658
[5] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3992 - 3995
[6] Tetrahedron, 2015, vol. 71, # 38, p. 6944 - 6955
[7] Chemical Communications, 2010, vol. 46, # 20, p. 3505 - 3507
[8] Journal of the American Chemical Society, 2017, vol. 139, # 41, p. 14676 - 14683
[9] Journal of the American Chemical Society, 2017, vol. 139, # 8, p. 2888 - 2891
[10] Molecules, 2017, vol. 22, # 11,
[11] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1193 - 1196
[12] Acta Crystallographica Section C: Crystal Structure Communications, 1997, vol. 53, # 9, p. 1329 - 1331
[13] Chemische Berichte, 1956, vol. 89, p. 2328,2330
[14] Bulletin de la Societe Chimique de France, 1975, p. 2121 - 2127
[15] Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 881 - 890
[16] Synthetic Communications, 2005, vol. 35, # 1, p. 129 - 135
[17] Organic Letters, 2000, vol. 2, # 4, p. 425 - 427
[18] Journal of Materials Chemistry, 2007, vol. 17, # 4, p. 364 - 371
[19] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 5, p. 725 - 731

2
[ 35168-62-8 ]
[ 15442-91-8 ]

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2012 - 2022
[2] Patent: US2865964, 1955, ,

3
[ 106-42-3 ]
[ 15442-91-8 ]

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2012 - 2022

[ 15442-91-8 ] Synthesis Path-Downstream 1~58

1
[ 95-93-2 ]
[ 15442-91-8 ]

Yield	Reaction Conditions	Operation in experiment
15%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 77℃; for 0.833333h;	1,2,4,5-tetrakis(bromomethyl)benzene (1c) was obtained by the reaction of 1,2,4,5-tetramethylbenzene(2.8 g; 20 mmol) with NBS (14.4 g; 80 mmol) and benzoyl peroxide (1 g; 5.9 mmol) in tetrachloromethane(50 mL). Reagents were heated at 77 C for 50 min. The precipitate was filtered off under reducedpressure and washed with hot tetrachloromethane. The filtrate was concentrated to small volume andcooled to 4 C. Crude product was filtrated and purified by crystallization from methanol. Rt< 1 h,white solid (15%), m.p. 159-160 C. 1H-NMR (CDCl3) delta: 7.37 ppm (2H, a), 4.60 ppm (8H, b). 13C-NMR(CDCl3) : 137.6 ppm (a), 133.6 ppm (h), 28.7 ppm (b). FT-IR (KBr) numax: 3026, 2980, 2933, 1504, 1456,1210, 911, 797, 678, 598.

Reference： [1]Journal of the Chinese Chemical Society,2002,vol. 49,p. 77 - 82
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 4281 - 4286
[3]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1994,vol. 247,p. 23 - 30
[4]Heterocycles,2015,vol. 90,p. 645 - 658
[5]Tetrahedron Letters,2015,vol. 56,p. 3992 - 3995
[6]Tetrahedron,2015,vol. 71,p. 6944 - 6955
[7]Chemical Communications,2010,vol. 46,p. 3505 - 3507
[8]Journal of the American Chemical Society,2017,vol. 139,p. 14676 - 14683
[9]Journal of the American Chemical Society,2017,vol. 139,p. 2888 - 2891
[10]Molecules,2017,vol. 22
[11]Journal of the American Chemical Society,2013,vol. 135,p. 1193 - 1196
[12]Acta Crystallographica, Section C: Crystal Structure Communications,1997,vol. 53,p. 1329 - 1331
[13]Chemische Berichte,1956,vol. 89,p. 2328,2330
[14]Bulletin de la Societe Chimique de France,1975,p. 2121 - 2127
[15]Journal of Organic Chemistry,1990,vol. 55,p. 881 - 890
[16]Synthetic Communications,2005,vol. 35,p. 129 - 135
[17]Organic Letters,2000,vol. 2,p. 425 - 427
[18]Journal of Materials Chemistry,2007,vol. 17,p. 364 - 371
[19]Zeitschrift fur Naturforschung, B: Chemical Sciences,2007,vol. 62,p. 725 - 731

2
[ 288-13-1 ]
[ 15442-91-8 ]
[ 172606-28-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetra(n-butyl)ammonium hydroxide; sodium hydroxide; In water; toluene; for 24h;Reflux; Inert atmosphere; Schlenk technique;	Ligand 1,2,4,5-tetrakis((1H-pyrazol-1-yl)methyl)benzene was synthesized with slight modification to a previously reported method [22]. A mixture of 1,2,4,5-tetrakis(bromomethyl)benzene (544.5 mg, 1.21 mmol), pyrazol (362.8 mg, 5.33 mmol), sodium hydroxide 40% (NaOH, 2.5 mL) and tetrabutylammonium hydroxide 40% (TBAH, 1 mL), was refluxed in toluene (14 mL) for 24 h.This dark brown solution was filtered off after addition of 20 mL of water. The pale yellow solid was washed with water and diethylether then dried under vacuum. Yield: 70%. Melting point: 173-175 C. Elemental Anal. Calc. for (C22H22N8)H2O: C, 63.45; N,26.90; H, 5.81. Found: C, 63.28; N, 26.67; H, 5.43%. ESI-MS (CHCl3):(L+) m/z 399.28. IR (KBr, cm1): m(CC) 1633, m(CN) 1514, m(C-H)3121. 1H NMR (DMSO-d6) (ppm) 7.65 (d, 4H, J(Hz) = 2.01); 7.42 (d,4H, J(Hz) = 1.45); 6.63 (s, 2H); 6.23 (t, 4H); 5.38 (s, 8H). 13C NMR(DMSO-d6) (ppm) 139.04 (C30); 135.30 (C1, C2, C4, C5); 130.14(C50); 129.05 (C3, C6); 105.56 (C40); 51.50 (C7). UV-Vis (DMSO)268 nm. e(268 nm, DMSO) = 437 M-1 cm-1.

Reference： [1]Polyhedron,2015,vol. 102,p. 321 - 328
[2]Australian Journal of Chemistry,1995,vol. 48,p. 1587 - 1600

3
[ 15442-91-8 ]
[ 82456-99-3 ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 141,p. 19823 - 19830
[2]Journal of Organic Chemistry,1995,vol. 60,p. 7293 - 7297
[3]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 164 - 170
[4]Journal of Organic Chemistry,1990,vol. 55,p. 881 - 890

4
[ 5932-27-4 ]
[ 15442-91-8 ]
1,2,4,5-tetrakis(3-ethyl ester pyrazole-1-yl-methyl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 10810 - 10820

5
[ 68631-52-7 ]
[ 15442-91-8 ]
C₅₄H₅₈N₄O₂₀ [ No CAS ]

Reference： [1]Synthetic Communications,2003,vol. 33,p. 1113 - 1119

6
[ 45676-04-8 ]
[ 15442-91-8 ]
C₃₈H₅₈N₈⁽⁴⁺⁾*4Br^(1-) [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1643 - 1646

7
[ 65838-10-0 ]
[ 15442-91-8 ]
C₅₀H₅₈N₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 3473 - 3478

8
[ 16532-79-9 ]
[ 15442-91-8 ]
[ 904930-09-2 ]
2,6-bis(4-bromophenyl)-1,2,3,5,6,7-hexahydro-s-indacene-2,6-dicarbonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 4281 - 4286

9
N-[2-(dimethylamino)ethyl]perfluoroundecanoic acid amide [ No CAS ]
[ 15442-91-8 ]
1,2,4,5-tetrakis[(N-(perfluoroundecanoamidoethyl)-N,N-dimethylammonium)methyl]benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 8663 - 8667

10
N-[2-(dimethylamino)ethyl]undecanoic acid amide [ No CAS ]
[ 15442-91-8 ]
1,2,4,5-tetrakis[(N-(undecanoamidoethyl)-N,N-dimethylammonium)methyl]benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 8663 - 8667

11
[ 624-92-0 ]
[ 15442-91-8 ]
[ 943545-86-6 ]

Reference： [1]Dalton Transactions,2007,p. 1986 - 1988
[2]Journal of Organometallic Chemistry,2009,vol. 694,p. 2299 - 2308

12
[ 1066-54-2 ]
[ 15442-91-8 ]
1,2,4,5-tetrakis(3-(trimethylsilyl)prop-2-yn-1-yl)benzene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 9776 - 9778
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9826 - 9834

13
[ 21819-66-9 ]
[ 15442-91-8 ]
C₃₄H₂₆N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 4h;	5-Amino-2-phenyl-2H-benzotriazole (Kehrmann, et. [AL.,] Chem. Ber. 1892,25, 899. ), 2.00 g, 9.51 [MMOL,] potassium carbonate, 3.47 g, 25.1 [MMOL,] and 1,2, 4,5- tetrakisbromomethylbenzene, 2.14 [G,] 4.76 [MMOL,] are placed in a 100 [ML] flask with a stir bar. DMF, 40 [ML,] is added and the mixture is heated to [100C.] After 4 hours, a thick yellow precipitate is found and TLC showed only one component with a very low Rf (1: 1 hexanes: ethyl acetate). The flask is cooled and water, 30 ml, is added. The product is filtered and washed several times with water, then with methanol. Remaining volatiles are removed in vacuo to give a yellow solid. Yield, 2.49 g, 4.56 mmol, 96%. Tm = [364C] ; T9 [=167C.] MS [(EL)] : 546 [(M+).]

Reference： [1]Patent: WO2003/105538,2003,A1 .Location in patent: Page 45, 46

14
[ 15442-91-8 ]
[ 120512-90-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetra(n-butyl)ammonium hydroxide; water; In 1,4-dioxane; at 90℃; for 6h;	To a mixture of <strong>[15442-91-8]1,2,4,5-tetrakis-(bromomethyl)-benzene</strong> (150 g, 0.33 mmol) and 1,4-dioxane (2L) was added a 55% aqueous solution of tetrabutylammonium hydroxide (640 mL) at room temperature, followed by stirring at 90 C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate after addition of a 2 N aqueous solution of hydrochloric acid (2L). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to give the title compound (35 g, 63% yield). 1H-NMR Spectrum (CDCl3) delta (ppm): 5.10 (8H, s), 7.08 (2H, s).

Reference： [1]Patent: US2013/197045,2013,A1 .Location in patent: Paragraph 0146; 0147; 0148
[2]Tetrahedron,2008,vol. 64,p. 4275 - 4286

15
[ 697-45-0 ]
[ 15442-91-8 ]
[ 1034024-75-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 7 To a stirred solution of 5,5-dimethyl-2-thioxo-[1,3,2]dioxaphosphorinane-2-thiol (9.70 g, 48 mmol) in toluene (110 mL) is added triethylamine (4.80 g, 48 mmol). The mixture is warmed to 45 C. To the resulting mixture is added 1,2,4,6-tetra(bromomethyl)benzene (5.0 g, 11 mmol) and the mixture is heated to reflux for 14 hours. The toluene solution is then filtered, and the precipitate is slurried in saturated aqueous sodium bicarbonate solution (100 mL). The precipitate is filtered, dried to yield a white solid, 2,2',2",2"'-[1,2,4,6-phenylenetetra(methylthio)]tetra[5,5-dimethyl-1,3,2-dioxaphosphorinane]-2,2',2",2"'-sulfide. The yield is 9.4 g (93%). The structure of the product is: The 5% WLT for this material is 281 C. Plaques made from a blend of 2.8% of the product in 97.2% polystyrene have an LOI of 24.3% and an FP-7 value of 5.6 s.

Reference： [1]Patent: US8058332,2011,B2 .Location in patent: Page/Page column 21-22

16
[ 10354-30-0 ]
[ 15442-91-8 ]
[ 1335204-18-6 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 39 - 46
[2]Canadian Journal of Chemistry,2011,vol. 89,p. 1236 - 1244

17
[ 166737-85-5 ]
[ 15442-91-8 ]
C₃₂H₃₀Br₂N₂OS [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1194 - 1197

18
[ 111-42-2 ]
[ 15442-91-8 ]
[ 1360545-16-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1194 - 1197

19
[ 33628-48-7 ]
[ 15442-91-8 ]
[ 1448782-65-7 ]

Yield	Reaction Conditions	Operation in experiment
41%		General procedure: 3a-acetoxy-5b-cholanicacid (200 mg, 0.48 mmol) was dissolved in anhydrous toluene (5 mL), themixture heated for 1 h, and DBU (0.1 mL, 0.62 mmol) was added. The mixturewas heated at reflux for 1 h, followed by the addition of 1,3,5-tris(bromomethyl)benzene (Aldrich) (60 mg, 0.168 mmol) and heating for anadditional 24 h. The mixture was poured onto ice, extracted with toluene(10 mL), and washed with H2O (15 mL) and brine (15 mL), and then dried overanhydrous MgSO4. Evaporation of the solvent and purification of the residueover silica gel (CHCl3/EtOAc, 50:1) gave 123 mg of product 7 (56%).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4700 - 4704

20
[ 52840-09-2 ]
[ 15442-91-8 ]
C₁₃₀H₁₉₀O₃₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%		General procedure: 3a-acetoxy-5b-cholanicacid (200 mg, 0.48 mmol) was dissolved in anhydrous toluene (5 mL), themixture heated for 1 h, and DBU (0.1 mL, 0.62 mmol) was added. The mixturewas heated at reflux for 1 h, followed by the addition of 1,3,5-tris(bromomethyl)benzene (Aldrich) (60 mg, 0.168 mmol) and heating for anadditional 24 h. The mixture was poured onto ice, extracted with toluene(10 mL), and washed with H2O (15 mL) and brine (15 mL), and then dried overanhydrous MgSO4. Evaporation of the solvent and purification of the residueover silica gel (CHCl3/EtOAc, 50:1) gave 123 mg of product 7 (56%).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4700 - 4704

21
[ 4057-84-5 ]
[ 15442-91-8 ]
[ 1448782-64-6 ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: 3a-acetoxy-5b-cholanicacid (200 mg, 0.48 mmol) was dissolved in anhydrous toluene (5 mL), themixture heated for 1 h, and DBU (0.1 mL, 0.62 mmol) was added. The mixturewas heated at reflux for 1 h, followed by the addition of 1,3,5-tris(bromomethyl)benzene (Aldrich) (60 mg, 0.168 mmol) and heating for anadditional 24 h. The mixture was poured onto ice, extracted with toluene(10 mL), and washed with H2O (15 mL) and brine (15 mL), and then dried overanhydrous MgSO4. Evaporation of the solvent and purification of the residueover silica gel (CHCl3/EtOAc, 50:1) gave 123 mg of product 7 (56%).

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4700 - 4704

22
[ 110-86-1 ]
[ 15442-91-8 ]
1,2,4,5-tetra(N-pyridiniummethyl)benzene tetrabromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 80℃; for 24h;	TBB-py: TBB (2 mmol, 0.9 g) and pyridine (8 mmol, 0.64 g) were dissolved in CH3CN (40 mL). After stirring for 24 h at 80 C, the white precipitate formed was filtered and washed with CH3CN for three times, and dried in vacuum at 80 C for 12 h. 1H NMR (400 MHz, D2O, TMS) delta(ppm) = 6.09 (s, 8 H, CH2), 6.77 (s, 2 H, CH), 8.10 (t, 8 H, CH),8.61 (t, 4H, CH), 8.86 (d, 8H, CH) (see Figure S1 in Supporting Informa-tion (SI)). CHN elemental analysis for TBB-py found (wt.%): C 47.05, H3.86, N 7.28

Reference： [1]CrystEngComm,2013,vol. 15,p. 8395 - 8399
[2]Catalysis Communications,2016,vol. 74,p. 99 - 103

23
[ 18438-38-5 ]
[ 15442-91-8 ]
[ 219872-10-3 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 5887 - 5889

24
[ 37797-12-9 ]
[ 15442-91-8 ]
9,9',9'',9'''-(4,4',4'',4'''-(benzene-1,2,4,5-tetrayltetrakis(methylene))tetrakis(oxy)tetrakis(benzene-4,1-diyl))tetrakis(3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: To a solution of 1 equiv. of xanthenes 5,6 and 7 in 5 ml of dry DMF, 2 equiv. of powdered K2CO3was added, stirred well for 30 min at room temperature. To that, alkylating agent (0.5 equiv. in case of dimers; 0.333 equiv. in case of trimers; 0.25 equiv. in case of tetramers dissolved in minimum amount of DMF was added drop wise for 1 hour with stirring at 50C.After the complete addition, the reaction mixture was stirred at 70C for 48hours. After completion of the reaction as indicated by TLC, the reaction mixture was poured into a beaker containing ice cold water and stirred well. The precipitate was collected and, if necessary, purified by column chromatography on silica gel (60-120 mesh). (The bipodal derivatives were purified using hexane/ethylacetate (75:25) solvent mixture where as tipodal and tetrapodal derivatives were purified using the chloroform/methanol(99.7:0.3) solvent mixture as Eluent).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 1401 - 1406

25
[ 37797-16-3 ]
[ 15442-91-8 ]
9,9',9'',9'''-(4,4',4'',4'''-(benzene-1,2,4,5-tetrayltetrakis(methylene))tetrakis(oxy)tetrakis(3,5-dimethoxybenzene-4,1-diyl))tetrakis(3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: To a solution of 1 equiv. of xanthenes 5,6 and 7 in 5 ml of dry DMF, 2 equiv. of powdered K2CO3was added, stirred well for 30 min at room temperature. To that, alkylating agent (0.5 equiv. in case of dimers; 0.333 equiv. in case of trimers; 0.25 equiv. in case of tetramers dissolved in minimum amount of DMF was added drop wise for 1 hour with stirring at 50C.After the complete addition, the reaction mixture was stirred at 70C for 48hours. After completion of the reaction as indicated by TLC, the reaction mixture was poured into a beaker containing ice cold water and stirred well. The precipitate was collected and, if necessary, purified by column chromatography on silica gel (60-120 mesh). (The bipodal derivatives were purified using hexane/ethylacetate (75:25) solvent mixture where as tipodal and tetrapodal derivatives were purified using the chloroform/methanol(99.7:0.3) solvent mixture as Eluent).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 1401 - 1406

26
[ 37797-15-2 ]
[ 15442-91-8 ]
9,9',9'',9'''-(4,4',4'',4'''-(benzene-1,2,4,5-tetrayltetrakis(methylene))tetrakis(oxy)tetrakis(3-methoxybenzene-4,1-diyl))tetrakis(3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%		General procedure: To a solution of 1 equiv. of xanthenes 5,6 and 7 in 5 ml of dry DMF, 2 equiv. of powdered K2CO3was added, stirred well for 30 min at room temperature. To that, alkylating agent (0.5 equiv. in case of dimers; 0.333 equiv. in case of trimers; 0.25 equiv. in case of tetramers dissolved in minimum amount of DMF was added drop wise for 1 hour with stirring at 50C.After the complete addition, the reaction mixture was stirred at 70C for 48hours. After completion of the reaction as indicated by TLC, the reaction mixture was poured into a beaker containing ice cold water and stirred well. The precipitate was collected and, if necessary, purified by column chromatography on silica gel (60-120 mesh). (The bipodal derivatives were purified using hexane/ethylacetate (75:25) solvent mixture where as tipodal and tetrapodal derivatives were purified using the chloroform/methanol(99.7:0.3) solvent mixture as Eluent).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 1401 - 1406

27
[ 606-23-5 ]
[ 15442-91-8 ]
[ 1476048-26-6 ]
C₁₉H₁₄Br₂O₂ [ No CAS ]
C₂₈H₁₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%; 30%; 18%	With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In acetonitrile; at 20℃; for 8h;	General procedure: To a solution of compounds 10b-c, 10g or 10j, K2CO3 (5equiv) and TBAHS (0.5equiv) in dry MeCN (25mL), tetra-bromo derivative 16 (1.2equiv) was added and the reaction mixture was stirred at rt for 12-16h. At the conclusion of reaction (TLC monitoring), excess amount of K2CO3 was filtered through the sintered glass funnel and the aqueous layer was extracted with CH2Cl2. The solvent was removed under reduced pressure and the crude products were purified by silica gel column chromatography using appropriate mixtures of EtOAc-petroleum ether to deliver the expected products 14b (8%, 355mg from 1.5g of 10b, 8h), 14b? (30%, 1.33g from 1.5g of 10b, 8h), 14c (60%, 853mg from 500mg of 10c, 12h), 14g (68%, 404mg from 250mg of 10g, 8h), and 14j (55%, 350mg from 300mg of 10j, 8h), along with the dimeric products 17b-c, and 17g. The 1H and 13C NMR spectra of these compounds matched with the reported spectral data.

Reference： [1]Heterocycles,2015,vol. 90,p. 645 - 658
[2]Tetrahedron,2015,vol. 71,p. 6944 - 6955

28
[ 61-70-1 ]
[ 15442-91-8 ]
C₁₉H₁₇Br₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In acetonitrile; at 20℃;	General procedure: Toa solution of the compounds 13a-c, K2CO3(5 equiv) and TBAHS (0.5 equiv) in dry MeCN (20 mL), 1,2,4,5-Tetrakis(bromomethyl)benzene11 (1.2 equiv) was addedand stirred the reaction mixture at rt for 12-24 h. At the conclusion ofreaction (TLC monitoring), excess amount of K2CO3 wasfiltered through the sintered glass funnel and the aqueous layer was extractedwith CH2Cl2. The solvent was removed under reducedpressure and the crude products 14a-cwere directly subjected to next step without further purification.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 3992 - 3995

29
[ 214610-10-3 ]
[ 15442-91-8 ]
C₂₃H₂₃Br₂NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In acetonitrile; at 20℃;	General procedure: Toa solution of the compounds 13a-c, K2CO3(5 equiv) and TBAHS (0.5 equiv) in dry MeCN (20 mL), 1,2,4,5-Tetrakis(bromomethyl)benzene11 (1.2 equiv) was addedand stirred the reaction mixture at rt for 12-24 h. At the conclusion ofreaction (TLC monitoring), excess amount of K2CO3 wasfiltered through the sintered glass funnel and the aqueous layer was extractedwith CH2Cl2. The solvent was removed under reducedpressure and the crude products 14a-cwere directly subjected to next step without further purification.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 3992 - 3995

30
[ 37994-11-9 ]
[ 15442-91-8 ]
C₂₁H₁₇Br₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In acetonitrile; at 20℃;	General procedure: Toa solution of the compounds 13a-c, K2CO3(5 equiv) and TBAHS (0.5 equiv) in dry MeCN (20 mL), 1,2,4,5-Tetrakis(bromomethyl)benzene11 (1.2 equiv) was addedand stirred the reaction mixture at rt for 12-24 h. At the conclusion ofreaction (TLC monitoring), excess amount of K2CO3 wasfiltered through the sintered glass funnel and the aqueous layer was extractedwith CH2Cl2. The solvent was removed under reducedpressure and the crude products 14a-cwere directly subjected to next step without further purification.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 3992 - 3995

31
[ 105-53-3 ]
[ 15442-91-8 ]
C₁₇H₂₀Br₂O₄ [ No CAS ]
[ 192826-88-3 ]

Yield	Reaction Conditions	Operation in experiment
39%; 25%		General procedure: To a suspension of sodium hydride (3equiv) in dry THF (20mL), compounds 10a, 10d-f or 10h-i were added and the reaction mixture was stirred at rt for 10min. Later, tetrabromo compound 16 (1.2equiv) was added and the stirring was continued at the same temperature for 8-12h. At the conclusion of the reaction (TLC monitoring), the reaction mixture was quenched with EtOAc and the solvent was removed under reduced pressure. The aqueous layer was extracted with CH2Cl2 and the crude products were purified using appropriate mixtures of EtOAc-petroleum ether to deliver the expected products 14a (39%, 1.09g from 1g of 10a, 12h), 14d (40%, 636mg from 500mg of 10d, 8h), 14e (48%, 285mg from 200mg of 10e, 12h), 14f (44%, 580mg from 500mg of 10f, 20h), 14h (32%, 175mg from 200mg of 10h, 24h) and 14i (36%, 204mg from 300mg of 10i, 15h), along with the dimeric products 17a and 17d-f products. The 1H and 13C NMR spectra of these compounds matched with the literature reported spectral data