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[ CAS No. 1134-35-6 ] {[proInfo.proName]}

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Chemical Structure| 1134-35-6
Chemical Structure| 1134-35-6
Structure of 1134-35-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1134-35-6 ]

CAS No. :1134-35-6 MDL No. :MFCD00006441
Formula : C12H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :NBPGPQJFYXNFKN-UHFFFAOYSA-N
M.W : 184.24 Pubchem ID :14338
Synonyms :
4,4'-Dimethyl-2,2'-bipyridine

Calculated chemistry of [ 1134-35-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.4
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 3.43
Consensus Log Po/w : 2.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.21 mg/ml ; 0.00114 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.758 mg/ml ; 0.00411 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.94
Solubility : 0.0021 mg/ml ; 0.0000114 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 1134-35-6 ]

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

Application In Synthesis of [ 1134-35-6 ]

* 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.

  • Upstream synthesis route of [ 1134-35-6 ]
  • Downstream synthetic route of [ 1134-35-6 ]

[ 1134-35-6 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 1134-35-6 ]
  • [ 6813-38-3 ]
YieldReaction ConditionsOperation in experiment
98% at 65℃; for 6 h; 1.0 g of 4,4-dimethyl-2,2-bipyridine(5.4mmol) was added to the reaction flask, 18mL concentrated sulfuric acid was slowly added dropwise and stirred, the process a lot of heat until the solution was cooled to room temperature and then added potassium dichromate 3.3g (11.3mmol), then the solution becomes dark green, Then reacted at 65 ° C for 6 h. The reaction was completed and cooled to room temperature, the reaction was added to 1000mL of water, a large number of white flocculent precipitate was generated at this time, suction filtration, and then washed with water and methanol to the filtrate was white precipitate was clarified, and then dried in a vacuum oven at 60 18h, Yield 98percent
96% With potassium permanganate; nitric acid In water at 80℃; for 6 h; In a four-necked flask equipped with a thermometer, a magnet and a reflux condenser,3.7 g (0.02 mol) of analytically pure 4,4'-dimethyl-2,2'-bipyridine was added,Was dissolved in a mixed system of 40 mL of water and 0.4 mL of nitric acid and heated to 80 ° C with stirring,And the temperature was maintained five times by adding potassium permanganate solid (12.6 g, 0.08 mol)Until the previous addition of potassium permanganate reaction to dissolve, then add the next batch of potassium permanganate,The reaction was stopped after 6 hours. After cooling to room temperature, the reaction solution is decompressed under reduced pressure, and after the insoluble matter is to be filtered out,Concentrate hydrochloric acid was added to the filtrate to adjust the pH to 1.Static crystallization, a white crystal precipitation.After crystallization was complete, the filtrate was decompressed under reduced pressure and the resulting white crystals were washed with deionized water.The product was then dried in vacuo to give 4.69 g of the desired product, 2,2'-bipyridyl-4,4'-dicarboxylic acid, in 96percent yield.
95%
Stage #1: for 0.25 h;
Stage #2: at 70 - 80℃; for 1 h;
To a 125 ml of sulfuric acid (98percent), 5.0 g (0.021 mol) of 4,4’-dimethyl-2,2’-bipyridine was added. The obtained mixture was stirred for about 15 min, and a clarified solution with a light pink color was achieved. Then 24 g (0.082 mol) of potassium dichromate was addedcarefully in small portions. And the temperature was held consistently between 70 and 80 °C during this process. After all the dichromate was added, the reaction was stirred for another one hour. The deep green mixture was then poured over 1000 mL of ice H2O and filtered. The solid was washed with H2O and allowed to dry. The resulting light yellow solid was thenrefluxed in 170 mL of 50percent HNO3 for 4h. This reaction solution was poured into into 1 L ofice water. A white powder was isolated by suction filtration and washed with H2O (6.1 g,95percent).
81% at 70℃; for 1 h; A solution of 4,4'-dimethyl-2,2'-bipyridine (2.00 g, 10.9 mmol) in concentratedsulfuric acid (50 mL) was heated to 70 C. Potassium dichromate(9.63 g, 32.6 mmol) was added very slowly. Heating and stirring was maintained for 1 h, and then the hot solution was poured onto ice (300 g) and stirred for 1 h. A fine yellow solid formed. This was filtered and washed with water. The crude product was suspendedin 50percent aqueous nitric acid (50 mL) and heated to 120 C for 4 h. Thesuspension was allowed to cool to room temperature and then poured onto ice (300 g). The suspension was allowed to sit overnight,and the resulting white solid was collected by vacuum filtrationand washed with water. The solid was then thoroughly dried in a flask under vacuum to yield a white solid
77% With chromium(VI) oxide; sulfuric acid In water for 48 h; Approximately 1 gram (5.43 mmol) 4,4'-dimethyl-2,2'-bipyridine was added to 40 ml of concentrated H2SO4. The solution was cooled to 0° C., and 3.3 grams of CrO3 was added slowly, forming a yellow solution. The solution was stirred for two days, after which the solution had turned dark green, and was then poured into ice water. A green precipitate formed that was filtered off and washed with water. The precipitate was then suspended in 50 ml water followed by the addition of a 10 M solution of KOH until the solution was basic, about pH equal to or greater than 8. The solution was filtered, the filtrate containing the desired product. The solution was acidified with HCl to precipitate the diacid product as a white solid, which was washed with water, methanol, and ether, and then dried to yield 1.017 grams of product, which was 77percent of the theoretical yield
34%
Stage #1: With selenium(IV) oxide In 1,4-dioxane for 3.5 h; Reflux
Stage #2: for 4 h; Reflux
4,4'-Dicarboxy-2,2'-bipyridine was synthesized via oxidation of4,4'-dimethyl-2,2'-bipyridine. The procedure outlined below ismodified from that previously reported [110]; however, NMR peakassignments are consistent with the literature [110]. Seleniumoxide (5.27 g, 0.0475 mol) was added to 4,4'-dimethyl-2,2'-bipyridine(2.04 g, 0.0111 mol) in 135 mL of 1,4-dioxane. The reactionmixture was heated to reflux with stirring for 3.5 h. After coolingto room temperature, black solid byproduct was removed by vacuumfiltration; the solvent was removed from the filtrate by rotaryevaporation, yielding a red solid. The resulting red solid was dissolvedin 35 mL of concentrated nitric acid. The solution wasslowly heated to reflux with stirring for 4 h. Red fumes were producedupon the addition of the nitric acid and throughout thereflux. The solution was cooled to room temperature and pouredover 180 mL of ice water to crystallize the yellow solid. The productwas isolated from the solution by vacuum filtration. Yield:0.92 g, 34percent. 1H NMR (CDCl3/TMS, 60 MHz): δ/ppm = 8.62 (d, 2H),8.22 (s, 2H), 7.27 (d, 2H).

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  • 2
  • [ 1134-35-6 ]
  • [ 6813-38-3 ]
  • [ 103946-54-9 ]
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  • 3
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  • [ 71071-46-0 ]
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  • [ 1134-35-6 ]
  • [ 56100-19-7 ]
YieldReaction ConditionsOperation in experiment
45 %Chromat. With nickel(II) bromide hydrate; sodium iodide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Inert atmosphere General procedure: The controlled current preparative electrolysis were carried out with a potentiostat/galvanostat equipment. Undivided cells with 20 mL compartment were used. Zn or Fe metallic rod with 8 mm diameter was used as the sacrificial anode. Ni foam (6 cm.x.3.5 cm) was used as the cathode. It could be re-used after washing with a 6 M HCl solution following by water and acetone, and dried. The same solution was used to clean the anode. A 5 mL DMF solution containing 7percent or 20percent of NiBr2*xH2O or [Ni(bpy)]Br221 and x mmol of the corresponding mixture of 2-bromomethylpyridines or 2,6-dihalopyridines (heterocouplings in Table 1, Table 2, Table 4 and Table 5), or (2.5 mmol) of 2,6-dihalopyridines (homocoupling in Table 3) was stirred or sonicated before the electrolysis, to ensure the solubilization of reagents. A pre-electrolysis was carried out with 15 mL of the electrolytic solution (DMF, 0.1 M NaI and 0.75 mmol of 1,2-dibromoethane), passing a charge of 146 C (I=150 mA). Then, the previous prepared solution of bromopicoline or bromopyridine and the catalyst in 5 mL DMF, was added to the electrolytic cell and the constant current electrolysis (I=100 mA) applied. It is important to ensure that the cell potential must not exceed 1.8 V in order to avoid the reduction of the substrate on the cathode surface. After the total consumption of the reagent (number of coulombs described in the tables), the reaction was stopped and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with several portions of a 6 M NH4OH solution. After drying over Na2SO4, the organic layer was evaporated under reduced pressure.
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  • 6
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  • [ 56100-19-7 ]
YieldReaction ConditionsOperation in experiment
35 %Chromat. With nickel(II) bromide hydrate; sodium iodide In N,N-dimethyl-formamide at 20℃; Electrochemical reaction; Inert atmosphere General procedure: The controlled current preparative electrolysis were carried out with a potentiostat/galvanostat equipment. Undivided cells with 20 mL compartment were used. Zn or Fe metallic rod with 8 mm diameter was used as the sacrificial anode. Ni foam (6 cm.x.3.5 cm) was used as the cathode. It could be re-used after washing with a 6 M HCl solution following by water and acetone, and dried. The same solution was used to clean the anode. A 5 mL DMF solution containing 7percent or 20percent of NiBr2*xH2O or [Ni(bpy)]Br221 and x mmol of the corresponding mixture of 2-bromomethylpyridines or 2,6-dihalopyridines (heterocouplings in Table 1, Table 2, Table 4 and Table 5), or (2.5 mmol) of 2,6-dihalopyridines (homocoupling in Table 3) was stirred or sonicated before the electrolysis, to ensure the solubilization of reagents. A pre-electrolysis was carried out with 15 mL of the electrolytic solution (DMF, 0.1 M NaI and 0.75 mmol of 1,2-dibromoethane), passing a charge of 146 C (I=150 mA). Then, the previous prepared solution of bromopicoline or bromopyridine and the catalyst in 5 mL DMF, was added to the electrolytic cell and the constant current electrolysis (I=100 mA) applied. It is important to ensure that the cell potential must not exceed 1.8 V in order to avoid the reduction of the substrate on the cathode surface. After the total consumption of the reagent (number of coulombs described in the tables), the reaction was stopped and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2 and washed with several portions of a 6 M NH4OH solution. After drying over Na2SO4, the organic layer was evaporated under reduced pressure.
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  • 7
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  • [ 99970-84-0 ]
YieldReaction ConditionsOperation in experiment
45% With selenium(IV) oxide In 1,4-dioxane for 44 h; Inert atmosphere; Reflux General procedure: To a 100ml two-necked RB, dimethyl bipyridine 1 (500 mg, 0.00271 mol, 1.0 equiv.)was taken, added 100 mL of 1,4-dioxane drop wise and stirred to get a homogenous mixtureand the solution was purged with nitrogen for 15 min bubbling nitrogen into the dioxane withstirring. 0. 663 mg of SeO2 (2.2 equiv) was added and refluxed under N2 atmosphere for 44hours. After the completion of the reaction (Monitored by TLC), the reaction mixture waswashed with warm 1,4-dioxane for 2 to 3 minutes and filtered and 1, 4-dioxane was removedunder reduced pressure. The residue was then dissolved in hot distilled ethyl acetate, filteredand again washed with hot ethyl acetate. The ethyl acetate layer was washed with 1MNa2CO3 (250ml) to remove additional carboxylic acid. The organic layer was dried withanhydrous Na2SO4 and concentrated and the residue was purified on alumina using 60percent ethylacetate in petroleum ether to afford the newly synthesized 2,2'-bipyridine 4,4'-dicarbaldehyde was thoroughly characterized by spectroscopic technique such as IR, 1HNMR, 13C NMR and HRMS.
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  • [ 142646-58-0 ]
YieldReaction ConditionsOperation in experiment
45% With n-butyllithium; diisopropylamine In tetrahydrofuran at 0 - 20℃; for 15 h; Inert atmosphere Diisopropylamine (28.0 mL, 0.160 mol, 2.66 equiv.) was dissolved in dry THF (60 mL) under an argon atmosphere. n-butylithium (107.0 mL, 0.160 mol, 2.66 equiv.) was added dropwise at 0 °C and the solution was stirred for 1 h. Afterwards, a solution of 4,4′-dimethyl-2,2′-bipyridine (11.0 g, 0.060 mol, 1 eq.) in dry THF (300 mL) was slowly added and the orange solution was stirred for 3 h. The reaction mixture was kept at 0 °C and bromooctane (28.0 mL, 0.160 mol, 2.66 equiv.) in dry THF (20 mL) was added. The reaction mixture was then allowed to warm to room temperature. After stirring for 12 h the reaction was quenched first with water (20 mL), then poured into an ice/ water mixture and extracted with diethylether. The resulting yellow oil was recrystallized from hexane, redissolved in DCM, extracted with diluted NaOH, dried over MgSO4, filtered and the solvent removed in vacuo. Drying in high vacuum yielded the desired product (11.02 g, 0.027 mol, 45 percent). 1H NMR (500 MHz, DMSO) δ in ppm= 8.85 (s, 1H), 8.83 (s, 1H), 7.28 (s, 1H), 7.27 (s, 1H), 2.68 (t, J= 7.6 Hz, 4H), 1.62 (p, J= 8.2, 6.9 Hz, 4H), 1.32–1.11 (m, 24H), 0.83 (t, J= 6.5 Hz, 6H). HRMS (ESI) m/z: [M+H]+ calcd. for (C28H44) 409.358; found 409.3581.
Reference: [1] Dyes and Pigments, 2014, vol. 104, p. 24 - 33
[2] Journal of the American Chemical Society, 1998, vol. 120, # 2, p. 305 - 316
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