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Chemistry
Heterocyclic Building Blocks
Pyridines
1,1-Di-n-octyl-4,4-bipyridinium Dibromide
Chemistry
Heterocyclic Building Blocks
Pyridines

[ CAS No. 36437-30-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 36437-30-6
Chemical Structure| 36437-30-6
Structure of 36437-30-6 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 36437-30-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 36437-30-6 ]

SDS Specification
Alternatived Products of [ 36437-30-6 ]

Product Details of [ 36437-30-6 ]

CAS No. :36437-30-6 MDL No. :MFCD00060051
Formula : C26H42Br2N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GVUBEJANEHZYPA-UHFFFAOYSA-L
M.W : 542.43 Pubchem ID :37451
Synonyms :

Calculated chemistry of [ 36437-30-6 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.62
Num. rotatable bonds : 15
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 144.21
TPSA : 7.76 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : -11.44
Log Po/w (XLOGP3) : 10.31
Log Po/w (WLOGP) : 0.66
Log Po/w (MLOGP) : 5.34
Log Po/w (SILICOS-IT) : 7.21
Consensus Log Po/w : 2.42

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -9.0
Solubility : 0.000000537 mg/ml ; 0.000000001 mol/l
Class : Poorly soluble
Log S (Ali) : -10.41
Solubility : 0.000000021 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -8.9
Solubility : 0.000000678 mg/ml ; 0.0000000012 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.1

Safety of [ 36437-30-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 36437-30-6 ]

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

  • Downstream synthetic route of [ 36437-30-6 ]

[ 36437-30-6 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 553-26-4 ]
  • [ 111-83-1 ]
  • [ 36437-30-6 ]
YieldReaction ConditionsOperation in experiment
98% In N,N-dimethyl-formamide at 105℃; for 18h; 1,10-Dioctyl-4,40-bipyridinium bis(trifluimide) [OctV2+][Tf2N]2was prepared as follows. A mixture of 1-bromooctane (45.6 mmol)and 4,40-bipyridyl (19.0 mmol) in DMF (20 mL) was heated to105 C for 18 h to give 1,10-dioctyl-4,40-bipyridinium dibromide([OctV2+][Br]2,5 18.6 mmol, 98%) as brilliant greenish yellow solids.A mixture of CH2Cl2 (10 mL) solution of [OctV2+][Br]2(5.54 mmol) and an aqueous solution (5 mL) of Li+[Tf2N](13.7 mmol) was stirred vigorously at room temperature for30 min to give [OctV2+][Tf2N]26 (5.15 mmol, 93%) as colorless solids.
84% In N,N-dimethyl-formamide at 105℃; for 12h;
62.4% In acetonitrile for 24h; Reflux;
47% In acetonitrile for 22h; Reflux; Preparation of 1,1'-dioctyl-4,4'-bipyridinium dibromide (8, PQ-8,8): To a solution of 4,4'-dipyridyl (1.00 g, 6.40 mmol) in acetonitrile (40 mL) was added octyl bromide (4.45 mL, 4.94 g, 25.6 mmol). The mixture was heated to reflux for 22 hours, then cooled and filtered. The filtered solid was rinsed with acetonitrile and hexane to afford the pure product (1.62 g, 47%) as yellow crystals: mp = 300.2-300.8 °C (dec.); 1H NMR (600 MHz, MeOD) δ 9.20-9.50 (m, 4 H), 8.60-8.80 (m, 4H), 4.60-4.90 (m, 4H), 2.00-2.20 (m, 4 H), 1.25-1.50 (m, 20 H), 0.80-1.00 (m, 6 H); low resolution mass spectrum (ESI) m/z 381.4 [(M-H)+; calcd for C26H41N2: 381.33].
31% In acetonitrile at 130℃; for 0.166667h; Microwave irradiation;
In N,N-dimethyl-formamide Heating;
In N,N-dimethyl-formamide for 8h; Heating;
In acetonitrile for 24h; Heating;
In N,N-dimethyl-formamide for 8h; Reflux;

Reference： [1]Kuroboshi, Manabu; Shiba, Takuya; Tanaka, Hideo [Tetrahedron Letters, 2013, vol. 54, # 28, p. 3666 - 3668]
[2]Location in patent: scheme or table Kuroboshi, Manabu; Kobayashi, Ryoto; Nakagawa, Takayuki; Tanaka, Hideo [Synlett, 2009, # 1, p. 85 - 88]
[3]Wang, Senlin; Wu, Hongshuai; Chen, Fanghui; Zhang, Yu; Zhang, Yuchen; Sun, Baiwang [RSC Advances, 2019, vol. 9, # 57, p. 33023 - 33028]
[4]Grenier, Melissa C.; Davis, Robert W.; Wilson-Henjum, Kelsey L.; Ladow, Jade E.; Black, Jacob W.; Caran, Kevin L.; Seifert, Kyle; Minbiole, Kevin P.C. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 4055 - 4058]
[5]Location in patent: scheme or table Lamberto, Massimiliano; Rastede, Elizabeth E.; Decker, Justyne; Raymo, Franisco M. [Tetrahedron Letters, 2010, vol. 51, # 42, p. 5618 - 5620]
[6]Adar, Eti; Degani, Yinon; Goren, Zafrir; Willner, Itamar [Journal of the American Chemical Society, 1986, vol. 108, # 16, p. 4696 - 4700]
[7]Maidan, Ruben; Goren, Zafrir; Becker, James Y.; Willner, Itamar [Journal of the American Chemical Society, 1984, vol. 106, # 21, p. 6217 - 6222]
[8]Liu, Yu; Li, Xiao-Yun; Zhang, Heng-Yi; Li, Chun-Ju; Ding, Fei [Journal of Organic Chemistry, 2007, vol. 72, # 10, p. 3640 - 3645]
[9]Dey, Nilanjan; Samanta, Suman K.; Bhattacharya, Santanu [Chemical Communications, 2017, vol. 53, # 9, p. 1486 - 1489]
  • 2
  • [ 36437-30-6 ]
  • C42H70O35*C26H43N2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris(2,2’-bipyridine)ruthenium(II); edetate disodium; β‐cyclodextrin In water Irradiation; phosphate buffer pH 5,5; effect of β-cyclodextrin,;
Reference： [1]Adar, Eti; Degani, Yinon; Goren, Zafrir; Willner, Itamar [Journal of the American Chemical Society, 1986, vol. 108, # 16, p. 4696 - 4700]
YieldReaction ConditionsOperation in experiment
With sodium dithionite In water at 25℃; pH 8.1 (0.1 M tris(hydroxymethyl)aminomethane/H2SO4); other solvents;
With sodium dithionite dimerization; also in the presence of polyelectrolytes ( sodium poly(styrenesulfonate, PSSNa and copolymer of maleic acid and cetyl vinyl ether, MA-CVE);
  • 4
  • [ 18958-57-1 ]
  • [ 36437-30-6 ]
  • [ 119108-99-5 ]
YieldReaction ConditionsOperation in experiment
74% In methanol; dichloromethane to soln. of Ni complex was dropped soln. of bipyridinium salt with vigorous stirring; after 3 d formed pptn. was filtered off and washed twice with CH2Cl2 and MeOH; recrystn. from DMA/MeOH; dried in high vac. for 24 h; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 5
  • [ 15607-55-3 ]
  • [ 36437-30-6 ]
  • [ 119108-93-9 ]
YieldReaction ConditionsOperation in experiment
79% With NaBH4 In tetrahydrofuran; dimethyl sulfoxide to suspn. of Pt complex (DMSO:THF = 1:2) was added NaBH4 in THF/MeOH (1:1), after 30 min mixt. was filtered into soln. of bipyridinium salt in MeOH; after 24 h formed crystals were filtered off and washed twice with MeOH and acetone; recrystn. from DMSO/MeOH; dried in high vac. for 2 d; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 6
  • [ 21954-15-4 ]
  • [ 36437-30-6 ]
  • [ 119108-92-8 ]
YieldReaction ConditionsOperation in experiment
70% With NaBH4 In tetrahydrofuran; dimethyl sulfoxide to suspn. of Pd complex (DMSO:THF = 1:2) was added NaBH4 in THF/MeOH (1:1), after 30 min mixt. was filtered into soln. of bipyridinium salt in MeOH; after 24 h formed crystals were filtered off and washed twice with MeOH and acetone; recrystn. from DMSO/MeOH; dried in high vac. for 2 d; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 7
  • tetra-n-butylammonium bis(1,3-dithiol-2-thione-4,5-dithiolato)nickelate(III) [ No CAS ]
  • [ 36437-30-6 ]
  • [ 119109-03-4 ]
YieldReaction ConditionsOperation in experiment
60% In methanol; acetone to soln. of Ni complex was slowly dropped soln. of bipyridinium salt in MeOH/acetone (2:1); after 2 d formed pptn. was filtered off and washed with MeOH and then with acetone; recrystn. from DMA/MeOH or DMSO/MeOH; dried in high vac. for 24 h; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 8
  • [N(C4H9)4]2[Ni(2-thioxo-1,3-dithiol-4,5-dithiolate)2] [ No CAS ]
  • [ 36437-30-6 ]
  • [ 119109-04-5 ]
YieldReaction ConditionsOperation in experiment
96% In acetone to soln. of Ni complex was slowly dropped soln. of bipyridinium salt in aq. acetone; after 2 d formed pptn. was filtered off and washed with acetone and MeOH; dried in high vac. for 24 h; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 9
  • bis(dithiobenzil)nickel [ No CAS ]
  • [ 36437-30-6 ]
  • [ 119108-91-7 ]
YieldReaction ConditionsOperation in experiment
81% With NaBH4 In tetrahydrofuran; dimethyl sulfoxide to suspn. of Ni complex (DMSO:THF = 1:2) was added NaBH4 in THF/MeOH (1:1), after 30 min mixt. was filtered into soln. of bipyridinium salt in MeOH; after 24 h formed crystals were filtered off and washed twice with MeOH and acetone; recrystn. from DMSO/MeOH; dried in high vac. for 2 d; elem. anal.;
Reference： [1]Nuesslein, Franz; Peter, Raimund; Kisch, Horst [Chemische Berichte, 1989, vol. 122, p. 1023 - 1030]
  • 10
  • [ 36437-30-6 ]
  • [ 90076-65-6 ]
  • 1,1'-dioctyl-4,4'-bipyridinium bis(trifluimide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% In dichloromethane; water at 20℃; for 0.5h;
93% In dichloromethane; water at 20℃; for 0.5h; 1,10-Dioctyl-4,40-bipyridinium bis(trifluimide) [OctV2+][Tf2N]2was prepared as follows. A mixture of 1-bromooctane (45.6 mmol)and 4,40-bipyridyl (19.0 mmol) in DMF (20 mL) was heated to105 C for 18 h to give 1,10-dioctyl-4,40-bipyridinium dibromide([OctV2+][Br]2,5 18.6 mmol, 98%) as brilliant greenish yellow solids.A mixture of CH2Cl2 (10 mL) solution of [OctV2+][Br]2(5.54 mmol) and an aqueous solution (5 mL) of Li+[Tf2N](13.7 mmol) was stirred vigorously at room temperature for30 min to give [OctV2+][Tf2N]26 (5.15 mmol, 93%) as colorless solids.
In methanol
Reference： [1]Location in patent: scheme or table Kuroboshi, Manabu; Kobayashi, Ryoto; Nakagawa, Takayuki; Tanaka, Hideo [Synlett, 2009, # 1, p. 85 - 88]
[2]Kuroboshi, Manabu; Shiba, Takuya; Tanaka, Hideo [Tetrahedron Letters, 2013, vol. 54, # 28, p. 3666 - 3668]
[3]Location in patent: experimental part Causin, Valerio; Saielli, Giacomo [Journal of Materials Chemistry, 2009, vol. 19, # 48, p. 9153 - 9162]
  • 11
  • [ 111-83-1 ]
  • 1-octyl-[4,4']bipyridinyl-1-ium bromide [ No CAS ]
  • [ 36437-30-6 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile for 24h; Reflux;
Reference： [1]Location in patent: experimental part Causin, Valerio; Saielli, Giacomo [Journal of Materials Chemistry, 2009, vol. 19, # 48, p. 9153 - 9162]
  • 12
  • [ 36437-30-6 ]
  • 2-[4,5-bis(methylthio)-1,3-dithiol-2-ylidene]-1,3-dithiol-4,5-dicarboxylate disodium salt [ No CAS ]
  • 2C10H7O4S6(1-)*C26H42N2(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In methanol at 40℃; for 24h; Sealed tube;
Reference： [1]Huo, Peng; Xue, Li-Jun; Li, Yan-Hong; Chen, Ting; Yu, Lei; Zhu, Qin-Yu; Dai, Jie [CrystEngComm, 2016, vol. 18, # 16, p. 2894 - 2900]
  • 13
  • [ 553-26-4 ]
  • [ 111-83-1 ]
  • [ 36437-30-6 ]
  • 1-octyl-[4,4']bipyridinyl-1-ium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.5% In 1,4-dioxane at 65℃; for 24h; Synthesis of N-octyl-4,4'-bipyridinium bromide, [C8Bipyr]Br 5 g (0.032 mol) of 4,4'-bipyridine was dissolved in 30 mL dry 1,4-dioxane in a two necked 100 mL round bottomed flask fitted with a condenser. 6.20 g (0.032 mol, 5.55 mL) of 1-bromooctane dissolved in 10 mL dry 1,4-dioxanewas added drop wise from a dropping funnel and the mixture was allowed to stir at 65 oC. After 24 h, a pale yellow precipitate was filtered from the reaction medium and characterized by 1H and 13C NMR spectroscopy. The result revealed that the product contained a mixture of monoalkylated and dialkylated 4,4'-bipyridinium bromides. 50 mL chloroform was used to extract the dialkylated product from the mixture. After filtration the chloroform was removed by evaporation in vacuo and the resulting solid dried under high vacuum for 4 hours. A white powder [C8Bipyr]Br was collected (yield 8.56 g, 76.5% [3].
11% In acetone at 50℃; for 66h; Synthesis of 1-0ctyl-4,4'-bipyridinium Hexafluorophosphate (2). A mixture of l-bromooctane (7.8mL, 45.O mmol), 4,4'-bipyridyl (4.7l g, 3O.2 mmol), and acetone (4O mL) was stirred at 5O oC for 66 h togive yellow precipitates. The resulting mixture was cooled to room temperature and poured into Et2O(lOO mL). The reaction mixture was filtered to remove 1,1'-dioctyl-4,4'-bipyrydinium dibromide[C8V2+][Br-]2 (l.77 g, 3.3 mmol, ll%) as brilliant greenish yellow solids. The filtrate was concentratedunder reduced pressure, and the residue was dissolved in deionized water (8O mL). To the solution wasadded an aqueous solution (2O mL) of NH4PF6 (5.5O g, 33.7 mmol). The whole mixture was stirredvigorously at room temperature for l h to afford precipitates. The precipitates were filtered and washedwith deionized water. The colorless solid was dried overnight in vacuo to give l-octyl-4,4'-bipyridinium hexafluorophosphate (2, 6.85 g, l6.5 mmol, 55%) as colorless solids.
Reference： [1]Abebe, Atakilt; Atlabachew, Minaleshewa [Bulletin of the Chemical Society of Ethiopia, 2017, vol. 31, # 3, p. 499 - 508]
[2]Kuroboshi, Manabu; Kojima, Atsuki; Tanaka, Hideo [Heterocycles, 2017, vol. 94, # 11, p. 2132 - 2140]

Tags: 36437-30-6 synthesis path| 36437-30-6 SDS| 36437-30-6 COA| 36437-30-6 purity| 36437-30-6 application| 36437-30-6 NMR| 36437-30-6 COA| 36437-30-6 structure

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