[ CAS No. 113682-56-7 ] {[proInfo.proName]}

Name: 113682-56-7|1,4-Di(pyridin-4-yl)benzene|97%
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Quality Control of [ 113682-56-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 113682-56-7 ]

Product Details of [ 113682-56-7 ]

CAS No. :	113682-56-7	MDL No. :	MFCD00445845
Formula :	C₁₆H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MAWKLXRVKVOYLR-UHFFFAOYSA-N
M.W :	232.28	Pubchem ID :	5250442
Synonyms :

Calculated chemistry of [ 113682-56-7 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.9
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.56
Log Po/w (XLOGP3) :	2.91
Log Po/w (WLOGP) :	3.81
Log Po/w (MLOGP) :	2.29
Log Po/w (SILICOS-IT) :	4.03
Consensus Log Po/w :	3.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.72
Solubility :	0.0441 mg/ml ; 0.00019 mol/l
Class :	Soluble
Log S (Ali) :	-3.11
Solubility :	0.179 mg/ml ; 0.000772 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.69
Solubility :	0.0000471 mg/ml ; 0.000000203 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 113682-56-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 113682-56-7 ]

* 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.

Upstream synthesis route of [ 113682-56-7 ]
Downstream synthetic route of [ 113682-56-7 ]

[ 113682-56-7 ] Synthesis Path-Upstream 1~10

1
[ 106-37-6 ]
[ 181219-01-2 ]
[ 113682-56-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; toluene for 48 h; Inert atmosphere; Reflux	Example 1 Synthesis of 4,4'-(1,4-phenylene)bis(1-hexylpyridin-1-ium) bis(tetrafluroborate) A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.34 g, 21.2 mmol), 1,4-dibromobenzene (2.00 g, 8.5 mmol), K₂CO₃ (2.92 g, 21.2 mmol) and Pd(PPh₃)₄ (0.49 g, 5 mol percent) in PhMe (30 mL) and EtOH (30 mL) under N₂ was heated at reflux for 48 h. The resulting mixture was poured into water (50 mL), extracted with dichloromethane (2*100 mL), dried (MgSO₄) and the solvent removed under reduced pressure. The residue was chromatographed on silica using MeOH (0-5percent) in dichloromethane as eluent. The solvent was removed under reduced pressure and the residue crystallised from hot EtOAc/hexanes to give 1,4-di(4-pyridyl)benzene (1.52 g, 77percent) as a pale yellow powder.
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In N,N-dimethyl-formamide; toluene at 130℃; for 48 h; Inert atmosphere	Pyridylboronic pinacol ester (3.64 g, 17.8 mmol), 1,4-dibromobenzene (1.40 g, 5.92 mmol), and Cs₂CO₃(11.6 g, 35.5 mmol) were added to a 1:1 mixture of dry PhMe/DMF (300 mL), which had been degassed with Ar for 15 min. Next, Pd(PPh₃)₄(0.68 g, 0.59 mmol) was added to the reaction mixture and the solution heated to 130° C. under Ar for 48 h. Then, the reaction mixture was cooled to room temperature and the palladium catalyst filtered off using Celite. The organic phase was concentrated under vacuum and then dissolved in CH₂Cl₂followed by extraction with H₂O three times. The organic layer was made acidic (pH 2-3) by adding dropwise concentrated HCl, which caused the desired product to precipitate from solution. The precipitate was collected by filtration and then dissolved in H₂O. Finally, aq. NaOH (10 M) was added dropwise to the water layer until the pH was 8-9, which resulted in precipitation of pure product ExBIPY (973 mg, 71percent) as a white solid. The yield of the product obtained in the reaction was 71percent. ¹H NMR (500 MHz, CDCl₃, ppm): δ_H8.72 (AA′ of AA′XX′, J=4.6, 1.6 Hz, 4H), 7.80 (s, 4H), 7.59 (XX′ of AA′XX′, J=4.6, 1.6 Hz, 4H).

Reference： [1] Patent: US2018/194995, 2018, A1, . Location in patent: Paragraph 0117
[2] Journal of the American Chemical Society, 2013, vol. 135, # 1, p. 183 - 192
[3] Patent: US2014/179017, 2014, A1, . Location in patent: Paragraph 0072
[4] Organic Letters, 2010, vol. 12, # 8, p. 1888 - 1891
[5] Chemistry - A European Journal, 2014, vol. 20, # 3, p. 649 - 652

2
[ 1120-87-2 ]
[ 4612-26-4 ]
[ 113682-56-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With C₃₇H₄₅ClN₂O₃PPd; potassium carbonate In ethanol; water at 80℃; for 6 h; Inert atmosphere; Schlenk technique	A 10-mL round-bottom flask was charged with the prescribe damount of catalyst, 1,4-benzenediboronic acid (0.5 mmol), N-heteroaryl halides (1.5 mmol), the selected base (1.5 mmol) and solvent (4 mL). The flask was placed in an oil bath and heated at 80 °C for 6 h, then cooled to room temperature and extracted with CH₂Cl₂. The crude products obtained from evaporation were purified by flash chromatography on silica gel. The products 5b–c, 5f, 5m [21], 5d [22], 5e [23], 5l [24] were known compounds and characterized by the comparison of data with those in the literature. The products 5a, 5g–k, 5n–o were new compounds and characterized by elemental analysis, IR, MS,¹H and ¹³C NMR.

Reference： [1] Transition Metal Chemistry, 2015, vol. 40, # 5, p. 501 - 508

3
[ 624-38-4 ]
[ 1692-15-5 ]
[ 113682-56-7 ]
[ 83420-59-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; methanol at 95℃; for 12 h; Inert atmosphere	General procedure: To a solution of diiodarene 1 or 5a–c (0.306mmol) in 1,4-dioxane/MeOH (2:1, 10mL) K₂CO₃ (126mg, 0.918mmol) was added. The mixture was degassed by bubbling nitrogen gas through it for 15min. Pd(PPh₃)₄ (17mg, 0.015mmol) was added and the solution was heated to 95°C. A solution of the boronic acid (0.275mmol) in 1,4-dioxane (5mL) was added dropwise to the reaction mixture for 10h using a syringe pump. After the addition was complete, the reaction mixture was stirred at 95°C for an additional 2h. It was then allowed to cool to room temperature, the solvent was removed under reduced pressure, the residue dispersed in CH₂Cl₂ (10mL). This suspension was washed with water, upon which the organic phase cleared up. It was dried dried over anhydrous CaCl₂, filtered and concentrated to dryness. The desired product was purified by chromatography on silica gel using 0→5percent CH₂Cl₂ in cyclohexane as eluent.

Reference： [1] Tetrahedron Letters, 2018, vol. 59, # 20, p. 1948 - 1951

4
[ 106-37-6 ]
[ 1692-15-5 ]
[ 113682-56-7 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 50, p. 14020 - 14030
[2] New Journal of Chemistry, 2018, vol. 42, # 4, p. 2526 - 2536
[3] Chemical Communications, 2015, vol. 51, # 43, p. 8998 - 9001
[4] Journal of the American Chemical Society, 2018, vol. 140, # 23, p. 7206 - 7212
[5] Chemical Communications, 2009, # 37, p. 5585 - 5587
[6] Inorganic Chemistry, 2013, vol. 52, # 8, p. 4205 - 4216
[7] Chemistry - A European Journal, 2015, vol. 21, # 45, p. 16083 - 16090

5
[ 106-37-6 ]
[ 59020-06-3 ]
[ 113682-56-7 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 7, p. 1855 - 1859
[2] Tetrahedron Letters, 1995, vol. 36, # 29, p. 5247 - 5250
[3] Journal of the Chemical Society, Chemical Communications, 1992, # 8, p. 620 - 622

6
[ 4612-26-4 ]
[ 19524-06-2 ]
[ 113682-56-7 ]

Reference： [1] Dalton Transactions, 2014, vol. 43, # 16, p. 6100 - 6107
[2] Inorganic Chemistry, 2014, vol. 53, # 14, p. 7591 - 7598

7
[ 106-46-7 ]
[ 1692-15-5 ]
[ 113682-56-7 ]

Reference： [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 10, p. 3430 - 3432

8
[ 2425-81-2 ]
[ 113682-56-7 ]

Reference： [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1993, # 5, p. 681 - 686

9
[ 110-86-1 ]
[ 13296-04-3 ]
[ 113682-56-7 ]
[ 113682-55-6 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1415 - 1416[2] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 7, p. 1573 - 1574

10
[ 553-26-4 ]
[ 113682-56-7 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 46, p. 16913 - 16922

[ 113682-56-7 ] Synthesis Path-Downstream 1~88

1
[ 106-37-6 ]
[ 59020-06-3 ]
[ 113682-56-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 1855 - 1859
[2]Tetrahedron Letters,1995,vol. 36,p. 5247 - 5250
[3]Journal of the Chemical Society. Chemical communications,1992,p. 620 - 622

2
C₁₆H₁₆N₂ [ No CAS ]
[ 113682-56-7 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 681 - 686

3
[ 877082-56-9 ]
[ 62938-08-3 ]
[ 113682-56-7 ]
C₄₆H₅₈N₂⁽²⁺⁾*C₂₄H₃₂O₆*2F₆P^(1-) [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 435 - 438

4
[ 110-86-1 ]
sodium carbonate [ No CAS ]
[ 113682-56-7 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 681 - 686

5
[ 2425-81-2 ]
[ 113682-56-7 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 681 - 686

6
[ 34843-18-0 ]
[ 113682-56-7 ]
{(NH₃)5RuNC₅H₄C₆H₄C₅H₄NRu(NH₃)5}⁽⁴⁺⁾*4PF₆^(1-)={(NH₃)5RuNC₅H₄C₆H₄C₅H₄NRu(NH₃)5}(PF₆)4 [ No CAS ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 3990 - 3992

7
dichloro(nitrosyl)[tris(3,5-dimethylpyrazolyl)-borato]molybdenum [ No CAS ]
[ 113682-56-7 ]
{(Mo(NO)(HB(C₃HN₂(CH₃)2)3)Cl)2(C₅H₄NC₆H₄C₅H₄N)} [ No CAS ]
{Mo(NO)(HB(C₃HN₂(CH₃)2)3)Cl(C₅H₄NC₆H₄C₅H₄N)} [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1993,p. 681 - 686
[2]Journal of the Chemical Society, Dalton Transactions,1993,p. 681 - 686

8
[ 67-56-1 ]
nickel(II) nitrate hexahydrate [ No CAS ]
[ 113682-56-7 ]
[ 71-43-2 ]
Ni(C₁₆H₁₂N₂)2(H₂O)2⁽²⁺⁾*C₆H₆*5CH₃OH*2NO₃^(1-)=NiC₃₂H₂₄N₄(H₂O)2(NO₃)2*C₆H₆*5CH₃OH [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,2000,p. 3805 - 3810

9
[ 553-26-4 ]
[ 113682-56-7 ]
nickel(II) nitrate [ No CAS ]
[ 71-43-2 ]
Ni⁽²⁺⁾*C₆H₄(C₅H₄N)2*(C₅H₄N)2*2NO₃^(1-)*6C₆H₆=[Ni(C₆H₄(C₅H₄N)2)((C₅H₄N)2)(NO₃)2](C₆H₆)6 [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 15 - 16

10
[ 67-56-1 ]
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 113682-56-7 ]
Co⁽²⁺⁾*2C₆H₄(C₅H₄N)2*2NO₃^(1-)*4H₂O*2CH₃OH=(Co(C₆H₄(C₅H₄N)2)2(H₂O)2)(NO₃)2*2H₂O*2CH₃OH [ No CAS ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 3976 - 3982

11
[ 7681-65-4 ]
[ 113682-56-7 ]
[ 887918-41-4 ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 6179 - 6187

12
[ 1050443-03-2 ]
[ 2923-28-6 ]
[ 113682-56-7 ]
[Cp(*)4Ir4(μ-chloranilato)2(μ-1,4-bis(4-pyridyl)benzene)2](triflate)4 [ No CAS ]

Reference： [1]Organometallics,2008,vol. 27,p. 4088 - 4097

13
[ 50475-22-4 ]
[ 113682-56-7 ]
[Pt₃(ethylenediamine)3(1,4-bis(4-pyridyl)benzene)3](NO₃)6 [ No CAS ]

Reference： [1]New Journal of Chemistry,2009,vol. 33,p. 264 - 270

14
[ 50475-22-4 ]
[ 113682-56-7 ]
[Pt₄(ethylenediamine)4(1,4-bis(pyridyl)benzene)4](NO₃)8 [ No CAS ]

Reference： [1]New Journal of Chemistry,2009,vol. 33,p. 264 - 270

15
2(Zn(C₁₁₆H₁₂₄N₁₀O₆))*N₂C₁₂H₆(N₄C₆₉H₇₂O₂)2 [ No CAS ]
[ 113682-56-7 ]
2Zn⁽²⁺⁾*2C₁₁₆H₁₂₄N₁₀O₆^(2-)*N₂C₁₆H₁₂*N₂C₁₂H₆(N₄C₆₉H₇₂O₂)2=(Zn(C₁₁₆H₁₂₄N₁₀O₆))2(N₂C₁₆H₁₂)*N₂C₁₂H₆(N₄C₆₉H₇₂O₂)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 5609 - 5620

16
2Zn⁽²⁺⁾*2Cu⁽¹⁺⁾*2C₁₁₆H₁₂₄N₁₀O₆^(2-)*N₂C₁₂H₆(N₄C₆₉H₇₂O₂)2*2PF₆^(1-)=(ZnC₁₁₆H₁₂₄N₁₀O₆)2Cu₂(N₂C₁₂H₆(N₄C₆₉H₇₂O₂)2)(PF₆)2 [ No CAS ]
[ 113682-56-7 ]
2Zn⁽²⁺⁾*2Cu⁽¹⁺⁾*2C₁₁₆H₁₂₄N₁₀O₆^(2-)*N₂C₁₆H₁₂*N₁₀C₁₅₀H₁₅₀O₄*2PF₆^(1-)=(ZnC₁₁₆H₁₂₄N₁₀O₆)2(N₂C₁₆H₁₂)Cu₂(N₁₀C₁₅₀H₁₅₀O₄)(PF₆)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 5609 - 5620

17
[ 106-37-6 ]
[ 1692-15-5 ]
[ 113682-56-7 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 14020 - 14030
[2]New Journal of Chemistry,2018,vol. 42,p. 2526 - 2536
[3]European Journal of Organic Chemistry,2019,vol. 2019,p. 1446 - 1460
[4]Chemical Communications,2015,vol. 51,p. 8998 - 9001
[5]Journal of the American Chemical Society,2018,vol. 140,p. 7206 - 7212
[6]Chemical Communications,2009,p. 5585 - 5587
[7]Inorganic Chemistry,2013,vol. 52,p. 4205 - 4216
[8]Chemistry - A European Journal,2015,vol. 21,p. 16083 - 16090
[9]Chemical Science,2019,vol. 10,p. 8806 - 8811

18
[ 113682-56-7 ]
[ 106-93-4 ]
2Br^(1-)*C₃₄H₂₈N₄⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2009,p. 5585 - 5587

19
[ 14267-08-4 ]
silver nitrate [ No CAS ]
[ 113682-56-7 ]
[ 67-68-5 ]
[(N,N,N',N'-tetramethylethylenediamine)Pd(1,4-bis(4-pyridyl)benzene)]3(NO₃)6*DMSO*4H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 2008 - 2015

20
[ 106-37-6 ]
[ 181219-01-2 ]
[ 113682-56-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 48h;Inert atmosphere; Reflux;	Example 1 Synthesis of 4,4'-(1,4-phenylene)bis(1-hexylpyridin-1-ium) bis(tetrafluroborate) A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.34 g, 21.2 mmol), 1,4-dibromobenzene (2.00 g, 8.5 mmol), K2CO3 (2.92 g, 21.2 mmol) and Pd(PPh3)4 (0.49 g, 5 mol percent) in PhMe (30 mL) and EtOH (30 mL) under N2 was heated at reflux for 48 h. The resulting mixture was poured into water (50 mL), extracted with dichloromethane (2*100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using MeOH (0-5percent) in dichloromethane as eluent. The solvent was removed under reduced pressure and the residue crystallised from hot EtOAc/hexanes to give 1,4-di(4-pyridyl)benzene (1.52 g, 77percent) as a pale yellow powder.
71%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In N,N-dimethyl-formamide; toluene; at 130℃; for 48h;Inert atmosphere;	Pyridylboronic pinacol ester (3.64 g, 17.8 mmol), 1,4-dibromobenzene (1.40 g, 5.92 mmol), and Cs2CO3 (11.6 g, 35.5 mmol) were added to a 1:1 mixture of dry PhMe/DMF (300 mL), which had been degassed with Ar for 15 min. Next, Pd(PPh3)4 (0.68 g, 0.59 mmol) was added to the reaction mixture and the solution heated to 130° C. under Ar for 48 h. Then, the reaction mixture was cooled to room temperature and the palladium catalyst filtered off using Celite. The organic phase was concentrated under vacuum and then dissolved in CH2Cl2 followed by extraction with H2O three times. The organic layer was made acidic (pH 2-3) by adding dropwise concentrated HCl, which caused the desired product to precipitate from solution. The precipitate was collected by filtration and then dissolved in H2O. Finally, aq. NaOH (10 M) was added dropwise to the water layer until the pH was 8-9, which resulted in precipitation of pure product ExBIPY (973 mg, 71percent) as a white solid. The yield of the product obtained in the reaction was 71percent. 1H NMR (500 MHz, CDCl3, ppm): deltaH 8.72 (AA? of AA?XX?, J=4.6, 1.6 Hz, 4H), 7.80 (s, 4H), 7.59 (XX? of AA?XX?, J=4.6, 1.6 Hz, 4H).

Reference： [1]Patent: US2018/194995,2018,A1 .Location in patent: Paragraph 0117
[2]Journal of the American Chemical Society,2013,vol. 135,p. 183 - 192
[3]Patent: US2014/179017,2014,A1 .Location in patent: Paragraph 0072
[4]Organic Letters,2010,vol. 12,p. 1888 - 1891
[5]Chemistry - A European Journal,2014,vol. 20,p. 649 - 652

21
[ 113682-56-7 ]
[ 74-88-4 ]
C₁₈H₁₈N₂⁽²⁺⁾*2I^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 7206 - 7212
[2]Organic Letters,2010,vol. 12,p. 1888 - 1891

22
[ 113682-56-7 ]
[ 160517-35-1 ]
[2TCA*3dpyb] [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 6299 - 6301

23
[ 1295300-38-7 ]
[ 113682-56-7 ]
C₅₂H₅₆N₈O₈⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2240 - 2250

24
C₁₆H₁₂N₂*C₁₇₀H₁₆₆N₁₀O₁₀Zn₂ [ No CAS ]
[ 113682-56-7 ]
2C₁₆H₁₂N₂*C₁₇₀H₁₆₆N₁₀O₁₀Zn₂ [ No CAS ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 1155 - 1157

25
C₁₆H₁₂N₂*C₁₈₆H₁₉₈N₁₀O₁₀Zn₂ [ No CAS ]
[ 113682-56-7 ]
2C₁₆H₁₂N₂*C₁₈₆H₁₉₈N₁₀O₁₀Zn₂ [ No CAS ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 1155 - 1157

26
C₁₇₀H₁₆₆N₁₀O₁₀Zn₂ [ No CAS ]
[ 113682-56-7 ]
C₁₆H₁₂N₂*C₁₇₀H₁₆₆N₁₀O₁₀Zn₂ [ No CAS ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 1155 - 1157

27
C₁₈₆H₁₉₈N₁₀O₁₀Zn₂ [ No CAS ]
[ 113682-56-7 ]
C₁₆H₁₂N₂*C₁₈₆H₁₉₈N₁₀O₁₀Zn₂ [ No CAS ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 1155 - 1157

28
zinc(II) nitrate hexahydrate [ No CAS ]
[ 100-21-0 ]
[ 113682-56-7 ]
[ 68-12-2 ]
([Zn₂(tetraphthalate)2(1,4-bis(4-pyridyl)benzene)]*2dimethylformamide*0.5water)n [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 9005 - 9013

29
[ 1263416-32-5 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
(CH₃C₆H₄CH(CH₃)2Ru)4(C₂O₄)2(C₆H₄(C₅H₄N)2)2⁽⁴⁺⁾*4OSO₂CF₃^(1-)*2H₂O=Ru₄C₇₆H₈₀N₄O₈(OSO₂CF₃)4*2H₂O [ No CAS ]

Reference： [1]Organometallics,2011,vol. 30,p. 6482 - 6489

30
[ 1263416-33-6 ]
[ 113682-56-7 ]
(CH₃C₆H₄CH(CH₃)2Ru)4(C₆H₂O₄)2(C₆H₄(C₅H₄N)2)2⁽⁴⁺⁾*4OSO₂CF₃^(1-)=Ru₄C₈₄H₈₄N₄O₈(OSO₂CF₃)4 [ No CAS ]

Reference： [1]Organometallics,2011,vol. 30,p. 6482 - 6489

31
[Ru₂(μ-η⁴-5,8-dioxido-1,4-naphtoquinonato)(η⁶-p-cymene)₂](SO₃CF₃)₂ [ No CAS ]
[ 113682-56-7 ]
(CH₃C₆H₄CH(CH₃)2Ru)4(C₁₀H₄O₄)2(C₆H₄(C₅H₄N)2)2⁽⁴⁺⁾*4OSO₂CF₃^(1-)=Ru₄C₉₂H₈₈N₄O₈(OSO₂CF₃)4 [ No CAS ]

Reference： [1]Organometallics,2011,vol. 30,p. 6482 - 6489

32
[ 67-56-1 ]
zinc(II) nitrate hexahydrate [ No CAS ]
1,1'-bisferrocenedicarboxylic acid [ No CAS ]
[ 113682-56-7 ]
[ 68-12-2 ]
([Zn(1,1'-ferrocenedicarboxylate-2H)(1,4-di(pyridin-4-yl)benzene)]*0.5DMF*0.5MeOH)n [ No CAS ]

Reference： [1]Dalton Transactions,2012,vol. 41,p. 3924 - 3927

33
[ 113682-56-7 ]
[ 627-18-9 ]
C₂₂H₂₆N₂O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 11076 - 11078

34
[ 106-46-7 ]
[ 1692-15-5 ]
[ 113682-56-7 ]

Reference： [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 3430 - 3432

35
[ 113682-56-7 ]
bis(4-bromomethyl) (bis-p-benzyl-4,4’-(1,4-phenylene)bispyridine)bis(hexafluorophosphate) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 183 - 192

36
[ 113682-56-7 ]
C₄₈H₄₀N₄⁽⁴⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 183 - 192

37
bis(4-bromomethyl) (bis-p-benzyl-4,4’-(1,4-phenylene)bispyridine)bis(hexafluorophosphate) [ No CAS ]
[ 113682-56-7 ]
C₄₈H₄₀N₄⁽⁴⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 183 - 192

38
[ 623-24-5 ]
[ 113682-56-7 ]
C₃₂H₂₈Br₂N₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetonitrile;	Bisbromomethyl(bis-p-benzyl-<strong>[113682-56-7]4,4'-(1,4-phenylene)bispyridine</strong>)bis(hexyfluorophosphate) (DB·2PF6) alpha,alpha'-Dibromop-xylene (4.58 g, 17.2 mmol) was added to CH2Cl2 (30 mL) in a 250 mL round-bottomed three-neck flask, and the resulting mixture was refluxed while stirring until all of the solid material dissolved. Next, the temperature of the oil bath was raised to 90° C., allowing the reaction mixture to reflux, while a suspension of ExBIPY (400 mg, 1.72 mmol) in MeCN (60 mL) was added in five aliquots slowly over 1 h. After only 30 min, however, a yellow precipitate, indicative of DB·2Br formation, began to appear. After heating under reflux for 48 h, the reaction mixture was cooled to room temperature, and the yellow precipitate was collected by filtration and washed with CH2Cl2. The yellow solid was dissolved in cold (?25° C.) MeOH (?500-750 mL) followed by the addition of NH4PF6 (?100-200 mg) and cold (?25° C.) H2O (?2 L), resulting in the precipitation of pure DB·2PF6 (1.41 g, 92percent) that was collected by filtration as a white solid. HRMS-ESI for DB·2PF6: calcd for C32H28Br2F12N2P2, m/z=743.0256 [M-PF6]+, 597.0536 [M-2PF6]2+. found, 743.0262 [M-PF6]+, 597.0538 [M-2PF6]2+. 1H NMR (500 MHz, CD3CN, ppm): deltaH 8.66 (AA' of AA'XX', J=6.9 Hz, 4H), 8.19 (XX' of AA'XX', J=6.9 Hz, 4H), 7.97 (s, 4H), 7.40 (AA' of AA'BB', J=8.2 Hz, 4H), 7.31 (BB' of AA'BB', J=8.2 Hz, 4H), 5.58 (s, 4H), 4.46 (s, 4H). 13C NMR (125 MHz, CD3CN, ppm): deltaC 155.0, 144.3, 139.9, 136.7, 132.9, 129.8, 129.1, 129.1, 125.6, 63.1, 32.3.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 183 - 192
[2]Patent: US2014/179017,2014,A1 .Location in patent: Paragraph 0040; 0048
[3]Journal of the American Chemical Society,2018,vol. 140,p. 7206 - 7212

39
[ 181188-86-3 ]
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 113682-56-7 ]
[Co(4,4'-(phenylazanediyl)dibenzoate)(1,4-bis(4-pyridyl)benzene)0.5*(H₂O)2]n [ No CAS ]

Reference： [1]CrystEngComm,2013,vol. 15,p. 616 - 627

40
zinc(II) nitrate hexahydrate [ No CAS ]
[ 2449-35-6 ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Zn₂(4,4'-sulfonyldibenzoate)₂(1,4-bis(4-pyridyl)benzene)]_*2(N,N-dimethylformamide) [ No CAS ]

Reference： [1]Inorganic Chemistry,2013,vol. 52,p. 3634 - 3642

41
Ni[Ni(CN)₄] [ No CAS ]
[ 113682-56-7 ]
Ni(1,4-bis(4-pyridyl)benzene)[Ni(CN)₄] [ No CAS ]

Reference： [1]Inorganic Chemistry,2013,vol. 52,p. 4205 - 4216

42
[ 67-56-1 ]
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer [ No CAS ]
[ 60-29-7 ]
Na₂(Cu(o-phenylenebis(oxamato))) [ No CAS ]
[ 7732-18-5 ]
[ 2923-28-6 ]
[ 113682-56-7 ]
12C₁₀H₁₅^(1-)*12Rh⁽³⁺⁾*6Cu⁽²⁺⁾*6C₁₀H₄N₂O₆^(4-)*6H₂O*17CH₄O*12CF₃O₃S^(1-)*2C₄H₁₀O*6C₁₆H₁₂N₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 8125 - 8128

43
bis(4-bromomethyl) (bis-p-benzyl-4,4’-(1,4-phenylene)bispyridine)bis(hexafluorophosphate) [ No CAS ]
[ 113682-56-7 ]
cyclobis((4,4’-phenylene)bispyridine-p-phenylene)tetrakis(chloride) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Two synthetic routes (Scheme 1), methods A (no template) and B (templated), were employed to prepare the tetracationic cyclophane. Method A: DB·2PF6 (312 mg, 0.350 mmol) and ExBIPY (81.3 mg, 0.350 mmol) were added to dry MeCN (200 mL) and stirred at room temperature. After 17 days, the reaction was stopped by adding concentrated HCl (2-3 mL), which caused the crude product to precipitate from solution. The precipitate was collected by filtration, dissolved in H2O, and precipitated again by adding NH4PF6 (100-200 mg). The solid material was collected by filtration and then subjected to column chromatography using silica gel and 1% NH4PF6 in MeCN (w/v) as the eluent. The final product was purified further through recrystallization in MeCN on slow vapor diffusion of iPrO2, yielding pure ExBox·4PF6 (83 mg, 19%) as a white solid. Method B: DB·2PF6 (312 mg, 0.350 mmol), ExBIPY (81.3 mg, 0.350 mmol), and the template pyrene (212 mg, 1.05 mmol) were added to dry MeCN (200 mL) and stirred at room temperature. After 17 days, the reaction was stopped by adding concentrated HCl (2-3 mL), causing the crude product to precipitate from solution. The yellowish-orange precipitate was collected by filtration and then dissolved in H2O, followed by extracting 5× with CH2Cl2 (200 mL per extraction). This solvent extraction step changes the organic layer from an orange solution to a white suspension, indicating that most, if not all, of the template had been removed. The extracted material was precipitated from solution by adding NH4PF6 (100-200 mg) before being subjected to column chromatography using silica gel and CH2Cl2/MeCN (1:1) and 1% NH4PF6 in MeCN (w/v) as the eluents, followed by recrystallization as in the case of nontemplated reaction to yield the pure product (184 mg, 42%) as a white solid. HRMS-ESI for ExBox·4PF6: calcd for C48H40F24N4P4, m/z=1107.2173 [M-PF6]+, 481.1263 [M-2PF6]2+. found, 1107.2184 [M-PF6]+, 481.1278 [M-2PF6]+. 1H NMR (500 MHz, CD3CN, ppm): deltaH 8.78 (AA? of AA?XX?, J=7.0 Hz, 8H), 8.18 (XX? of AA?XX?, J=6.9 Hz, 8H), 7.93 (s, 8H), 7.61 (s, 8H), 5.68 (s, 8H). 13C NMR (125 MHz, CD3CN, ppm): deltaC=155.5, 145.1, 137.4, 137.1, 131.1, 130.2, 126.7, 64.8. 1H NMR (500 MHz, CD3COCD3, ppm): deltaH 9.28 (AA? of AA?XX?, J=7.1 Hz, 8H), 8.51 (XX? of AA?XX?, J=7.1 Hz, 8H), 8.15 (s, 8H), 7.86 (s, 8H), 6.08 (s, 8H). 13C NMR (125 MHz, CD3COCD3, ppm): deltaC 155.2, 145.5, 137.4, 137.3, 131.3, 130.2, 126.6, 64.7.

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11962 - 11969
[2]Patent: US2014/179017,2014,A1 .Location in patent: Paragraph 0040; 0049

44
zinc(II) nitrate hexahydrate [ No CAS ]
[ 113682-56-7 ]
[ 114274-39-4 ]
[ 1580477-40-2 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2276 - 2291
[2]Chemical Communications,2015,vol. 51,p. 4872 - 4875

45
zinc(II) nitrate hexahydrate [ No CAS ]
[ 1580459-52-4 ]
[ 113682-56-7 ]
[ 1580477-42-4 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2276 - 2291

46
zinc(II) nitrate hexahydrate [ No CAS ]
[ 113682-56-7 ]
5-(pyren-1-ylmethoxy)isophthalic acid [ No CAS ]
[ 1580477-43-5 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2276 - 2291

47
[ 761442-02-8 ]
[ 1220714-37-3 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
[{(N,N,N',N'-tetramethylethylenediamine)Pd}₆(1,2,4,5-tetrakis(1-imidazolyl)benzene)₂(1,4-di(pyridin-4-yl)benzene)₂] [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1595 - 1598

48
[ 4612-26-4 ]
[ 19524-06-2 ]
[ 113682-56-7 ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 6100 - 6107
[2]Inorganic Chemistry,2014,vol. 53,p. 7591 - 7598

49
zinc(II) nitrate hexahydrate [ No CAS ]
[ 10397-52-1 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Zn2(3,3′,5,5′-tetracarboxylatediphenylmethane)(4,4'-bispyridylphenyl)]*3DMF*4H2O [ No CAS ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 6100 - 6107

50
potassium dicyanoargentate(I) [ No CAS ]
Fe⁽²⁺⁾*2ClO₄^(1-)*9H₂O = Fe(ClO₄)2*9H₂O [ No CAS ]
[ 113682-56-7 ]
[ 68-12-2 ]
[ 75-05-8 ]
[Fe(1,4-di(pyridin-4-yl)benzene){Ag(CN)2}{Ag2(CN)3}]·2DMF·MeCN [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 4039 - 4046

51
potassium dicyanoargentate(I) [ No CAS ]
Fe⁽²⁺⁾*2ClO₄^(1-)*9H₂O = Fe(ClO₄)2*9H₂O [ No CAS ]
[ 64-17-5 ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Fe(1,4-di(pyridin-4-yl)benzene){Ag(CN)2}{Ag2(CN)3}]·DMF·EtOH [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 4039 - 4046

52
potassium dicyanoargentate(I) [ No CAS ]
Fe⁽²⁺⁾*2ClO₄^(1-)*9H₂O = Fe(ClO₄)2*9H₂O [ No CAS ]
[ 113682-56-7 ]
[Fe(1,4-di(pyridin-4-yl)benzene)2{Ag(CN)2}2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 4039 - 4046

53
potassium chromate [ No CAS ]
nickel(II) chloride hexahydrate [ No CAS ]
[ 113682-56-7 ]
[Ni(bpb)2CrO₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	In water; acetonitrile; at 20℃; for 168h;Sealed tube;	I mL of acetonitrile and water (v/v = 1:2) was carefully layered over an aqueous solution (4 mL water and one drop acetonitrile) of NiCI2.6H20 (Sigma- Aldrich Inc., 98percent, 23.8 mg, 0.1 mmol) and K2CrO4 (Sigma-Aldrich Inc., 99percent, 19.4 mg, 0.1 mmol) in a long thin test tube. I ,4-bis(4-pyridyl)benzene (bpb) (has been synthesized according to the previously reported procedure1, 23.2 mg, 0.1 mmol) in 4 mL of acetonitrile and water (v/v = 2:1) was slowly layered over the buffer layer. The tube was sealed and left undisturbed at room temperature. After one week yellowish green crystals were isolated from the buffer layer (yield: 3 mg, 5percent based on NiCI2.6H20). Figure 10.1 illustrates the single crystal x-ray structure of CROFOUR-4-Ni viewed along [001], H atoms omitted for clarity.

Reference： [1]Patent: WO2014/74378,2014,A1 .Location in patent: Page/Page column 32

54
[ 7631-95-0 ]
nickel(II) chloride hexahydrate [ No CAS ]
[ 113682-56-7 ]
[Ni(bpb)2MoO₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	In water; acetonitrile; at 20℃; for 168h;Sealed tube;	Example 11:Synthesis and characterization of [Ni(bpb)2(Mo04)] (MOOFOU R-4-Ni):2 mL of acetonitrile and water (v/v = 1:2) was carefully layered over an aqueous solution (4 mL water and one drop acetonitrile) of NiCI2.6H20 (Sigma- Aldrich Inc., 98percent, 23.8 mg, 0.1 mmol) and Na2MoO4.2H20 (Sigma-Aldrich Inc., 98percent, 24.3 mg, 0.16 mmol) in a long thin test tube. I ,4-bis(4-pyridyl)benzene (bpb) (has been synthesized according to the previously reported procedure1, 23.2 mg, 0.1 mmol) in 4 mL of acetonitrile and water (v/v = 2:1) was slowly layered over the buffer layer. The tube was sealed and left undisturbed at room temperature. After one week light green crystals were isolated from the buffer layer (yield: 13 mg, 16percent based on NiCl2.6H20). Figure 11.1 illustrates the single crystal x-ray structure of MOOFOUR-4-Ni viewed along [001] (left). View of the cavity in MOOFOUR-4-Ni along [001] (right).atoms omitted for clarity.

Reference： [1]Patent: WO2014/74378,2014,A1 .Location in patent: Page/Page column 32

55
[ 121-91-5 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
[ 20667-12-3 ]
[[Ag2(1,4-bis(pyrid-4-yl)benzene)2(H2O)](1,3-benzenedicarboxylic acid(2-))·8H2O]n [ No CAS ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 8774 - 8780

56
[ 113682-56-7 ]
[ 75178-70-0 ]
C₂₀H₂₀N₈⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 6196 - 6199

57
cobalt(II) sulphate heptahydrate [ No CAS ]
[ 2215-89-6 ]
[ 113682-56-7 ]
[Co₅(1,4-di(pyridin-4-yl)benzene)₃(4,4′-oxydibenzoic acid)₄(4,4′-oxydibenzoic acid)₂(H₂O)₂] [ No CAS ]

Reference： [1]CrystEngComm,2014,vol. 16,p. 6354 - 6363

58
nickel(II) sulfate heptahydrate [ No CAS ]
[ 2215-89-6 ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Ni₂(1,4-di(pyridin-4-yl)benzene)₂(4,4′-oxydibenzoic acid)₂(DMF)(H₂O)]*2·5H₂O [ No CAS ]

Reference： [1]CrystEngComm,2014,vol. 16,p. 6354 - 6363

59
[ 113682-56-7 ]
cyclobis((4,4’-phenylene)bispyridine-p-phenylene)tetrakis(chloride) [ No CAS ]

Reference： [1]Patent: US2014/179017,2014,A1

60
zinc(II) nitrate hexahydrate [ No CAS ]
1,3-bis-(3,5-dicarboxyphenyl)imidazolium chloride [ No CAS ]
[ 113682-56-7 ]
[ 68-12-2 ]
[Zn₂(1,3-bis(3,5-dicarboxyphenyl)imidazolium)(1,4-bis(4-pyridyl)benzene)₂]*(NO₃)*(DMF)₃*(H₂O)₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 7591 - 7598

61
3,3′-carbonylbis(methylazanediyl)dibenzoic acid [ No CAS ]
[ 113682-56-7 ]
(3,3′-carbonylbis(methylazanediyl)dibenzoic acid)*(1,4-di(pyridine-4-yl)benzene) [ No CAS ]

Reference： [1]Crystal Growth and Design,2013,vol. 13,p. 2327 - 2334

62
[ 64-17-5 ]
[ 7732-18-5 ]
[ 4119-52-2 ]
[ 113682-56-7 ]
[Fe(1,4-bis(pyrid-4-yl)benzene)2(NCS)2]*3EtOH [ No CAS ]
[Fe(1,4-bis(pyrid-4-yl)benzene)2(NCS)2]*2.5H₂O [ No CAS ]

Reference： [1]Crystal Growth and Design,2014,vol. 14,p. 4891 - 4894

63
[ 1020-31-1 ]
[ 6147-53-1 ]
[ 113682-56-7 ]
[ 75-05-8 ]
[Co^II(3,5-di-tert-butylsemiquinone)₂(bpb)][Co^III(3,5-ditert-butylcatechol)(3,5-di-tert-butylsemiquinone)(1,4-bis(4-pyridyl)benzene)]_0.5*2CH₃CN*2H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 13212 - 13219

64
zinc(II) nitrate hexahydrate [ No CAS ]
[ 1052737-14-0 ]
[ 113682-56-7 ]
C₁₆H₁₂N₂*C₁₁H₆O₅^(2-)*Zn⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 4872 - 4875

65
[ 20248-86-6 ]
[ 113682-56-7 ]
bis(4,4′-bromomethylbiphenyl)(4,4′-(1,4-phenylene)bipyridin-1-ium) bis(hexafluorophosphate) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2392 - 2399

66
bis(4,4′-bromomethylbiphenyl)(4,4′-(1,4-phenylene)bipyridin-1-ium) bis(hexafluorophosphate) [ No CAS ]
[ 113682-56-7 ]
cyclobis(4,4′-(1,4-phenylene)bipyridin-1-ium-4,4′-biphenylenebis(methylene)) tetrakis(hexafluorophosphate) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 2392 - 2399

67
iron(II) selenocyanate [ No CAS ]
[ 64-17-5 ]
[ 75-09-2 ]
[ 7732-18-5 ]
[ 113682-56-7 ]
6C₁₆H₁₂N₂*3Fe⁽²⁺⁾*6CNSe^(1-)*2.01CH₂Cl₂*3.99C₂H₆O*2.01H₂O [ No CAS ]