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[ CAS No. 6813-38-3 ] {[proInfo.proName]}

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Chemical Structure| 6813-38-3
Chemical Structure| 6813-38-3
Structure of 6813-38-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 6813-38-3 ]

CAS No. :6813-38-3 MDL No. :MFCD00015430
Formula : C12H8N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :FXPLCAKVOYHAJA-UHFFFAOYSA-N
M.W : 244.20 Pubchem ID :688094
Synonyms :

Calculated chemistry of [ 6813-38-3 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.39
TPSA : 100.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.08
Log Po/w (XLOGP3) : 0.53
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : -0.99
Log Po/w (SILICOS-IT) : 1.22
Consensus Log Po/w : 0.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.98
Solubility : 2.54 mg/ml ; 0.0104 mol/l
Class : Very soluble
Log S (Ali) : -2.21
Solubility : 1.51 mg/ml ; 0.00618 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.292 mg/ml ; 0.00119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 6813-38-3 ]

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 [ 6813-38-3 ]

* 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 [ 6813-38-3 ]
  • Downstream synthetic route of [ 6813-38-3 ]

[ 6813-38-3 ] Synthesis Path-Upstream   1~19

  • 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
  • [ 6313-54-8 ]
  • [ 6813-38-3 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride; sodium hydroxide In methanol; water Example 5
5.00 g of 2-chloroisonicotinic acid and 2.80 g of sodium hydroxide are dissolved in a mixture of 20 ml of water and 16 ml of methanol.
Following the addition of 1.02 g of palladium (10percent by weight on activated carbon) as catalyst, the mixture is stirred for 6 h at 80-85° C. at 0.1 MPa.
The catalyst is then filtered off.
Following acidification to pH 1 using hydrochloric acid, the product, 2,2'-bipyridyl-4,4'-dicarboxylic acid, precipitates out as a white solid.
This gives 3.3 g (85percent yield).
Reference: [1] Patent: US6500956, 2002, B1,
  • 3
  • [ 1127385-14-1 ]
  • [ 6813-38-3 ]
YieldReaction ConditionsOperation in experiment
45% With nitric acid In water at 180℃; for 36.17 h; Heating 4,4′,6,6′-Tetracarboxy-2,2’-bipyridine (0.083g; 0.25mmol) was placed a 45ml Teflon®-lined digestion bomb in H2O (8ml) and conc. HNO3 (1ml). This was stirred for 10min, sealed, heated to 180°C for 36h and cooled at a rate of 5°C/h.
Reference: [1] Inorganica Chimica Acta, 2013, vol. 403, p. 102 - 109
  • 4
  • [ 104704-09-8 ]
  • [ 6813-38-3 ]
YieldReaction ConditionsOperation in experiment
49.8%
Stage #1: With silver nitrate; acetic acid In ethanol; water for 24 h;
Stage #2: With sodium hydroxide In ethanol; water for 0.333333 h;
2-neck round bottom flask (100 mL) to the 4'-Methyl-2, 2'-bipyridine-4-carbaldehyde (0.500 g, 2.53 mmol) in ethanol (20.0 mL) dissolved in water (H2O) (4.00 mL) in the addition of acetic acid dissolved (AgNO3) (0.500 g, 2.96 mmol).Using a dropping funnel (Dropping funnel) and stirred for 24 hours after addition of 10 mL 1.0 M sodium hydroxide solution (NaOH) for 20 minutes.After the reaction was completed it was concentrated and filtered with a filter paper.The filtered precipitate was washed with 2.0 M sodium hydroxide solution (NaOH) and water (H 2 O) and wash the aqueous layer with dichloromethane (Dichloromethane).Aligning the pH of the aqueous phase to 3, it was filtered through a filter paper to give worked indirect determination washed with diethyl ether (Diethyl ehter) to give a white solid product.(Yield: 49.8percent).
Reference: [1] Patent: KR2015/125064, 2015, A, . Location in patent: Paragraph 0061-0064
  • 5
  • [ 3052-28-6 ]
  • [ 6813-38-3 ]
Reference: [1] Patent: US2012/247561, 2012, A1,
  • 6
  • [ 18511-71-2 ]
  • [ 124-38-9 ]
  • [ 6813-38-3 ]
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  • 7
  • [ 71071-46-0 ]
  • [ 6813-38-3 ]
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  • 8
  • [ 1134-35-6 ]
  • [ 6813-38-3 ]
  • [ 103946-54-9 ]
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  • 9
  • [ 108-89-4 ]
  • [ 6813-38-3 ]
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  • 10
  • [ 1762-35-2 ]
  • [ 6813-38-3 ]
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  • 11
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  • [ 6813-38-3 ]
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  • 12
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  • [ 6813-38-3 ]
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  • 13
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  • 14
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  • [ 6813-38-3 ]
Reference: [1] Patent: US2012/247561, 2012, A1,
  • 15
  • [ 99970-84-0 ]
  • [ 6813-38-3 ]
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  • 16
  • [ 67-56-1 ]
  • [ 6813-38-3 ]
  • [ 71071-46-0 ]
YieldReaction ConditionsOperation in experiment
90% Reflux Dimethyl 2,2 '-bipyridine-4,4'-dicarboxylate (I)To a suspension of 2,2'-dipyridyl-4,4'-dicarboxylic acid (2.00 g, 8.10 mmol) in MeOH (150 mL) was added thionyl chloride (1492 μL, 20.48 mmol) dropwise. The mixture was stirred under reflux overnight. Then the solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and water (100 mL). The organic phase was washed through saturated NaHCO3(aq) for 3 times, dried over Na2SO4. The solvent was removed under reduced pressure to give the product as a white solid (2.00 g, 90percent).
88% With sulfuric acid In water at 105℃; Take the product I obtained 2g and 10mL 98percent H2SO4, 100mL CH3OH into the flask with a stirrer, reflux at 105 ° C overnight, the end of the reaction to a large amount of water appears white flocculent precipitate, slowly adding NaOH solution adjusted to pH 9.0 , With CH2C12 extract to retain the organic phase, anhydrous Na2S04 dry, evaporated to dry the solvent to obtain white crystals, the yield of 88percent.
86%
Stage #1: for 24 h; Reflux
Stage #2: With sodium hydroxide In water at 0℃;
General procedure: The 4,4'-bis[C(0)OR]-2,2'-bipyridine ligands (L-COOCi to L-COOC4) were synthesized as described elsewhere for the synthesis of L-COOCi (Liu et al, Polymer 52:3318-3324, 2011), with slight modifications of the procedure. Briefly, concentrated sulfuric acid (20.4 equiv) was slowly added to a suspension of 4,4'-dicarboxylic acid-2,2'- bipyridine (1 equiv) in the desired alcohol (~ 25 ml of alcohol per 1 g of diacid used). Once the heat subsided, the reaction mixture was refluxed for 24 hours. At the end of the reaction, the volume of the resulting bright, hot pink solution was reduced using a rotary evaporator. The crude product was precipitated out in ice water and neutralized with a 40percent NaOH solution. The pure product was obtained by recrystallization in ethanol, unless otherwise noted. L-COOCi [00215] Yield: 86percent. Mp = 210.0°C [lit. mp = 210-211°C (Case, J Am Chem Soc 68:2574-2577, 1946). XH NMR (298 K, 400 MHz, DMSO-): δ (ppm) = 8.94 (d, J= 4.9 1H), 8.85 (d, J= 0.6 Hz, 1H), 7.93 (dd, J= 5.0, 1.7 Hz, 1H), 3.97 (s, 3H)
76% at 105℃; for 12 h; Weigh 4,4'-dicarboxy-2,2'-bipyridine 500mg (2.05mmol) was added to the reaction flask, 100mL of methanol was added, 8mL of concentrated sulfuric acid was slowly added dropwise and stirred at 105 for 12h. After the reaction was completed and cooled to room temperature, the reaction was added to 500 mL of water, and the pH was adjusted to 9 using saturated NaOH solution. After the pH was adjusted, 200 mL of dichloromethane solution was added and allowed to stand still. At this time, a white flocculent precipitate was formed and the supernatant was poured out. The lower layer was extracted with dichloromethane and water (3 × 100 mL), the organic phase was extracted and dried to give the product , Yield 76percent.

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  • 17
  • [ 186581-53-3 ]
  • [ 6813-38-3 ]
  • [ 71071-46-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium hydroxide In diethyl ether; chloroform at 20℃; An ether solution (30 mL) of CH2N2 prepared from N-methyl-N-nitrosourea (2.18 g, 21.2 mmol) and 50percent aqueous KOH (10 mL) was added dropwise to stirred suspension of 2,2'-bipyridine-4,4'-dicarboxylic acid 4a (1.00 g, 4.10 mmol) in CHCl3 (80 mL) at ambient temperature. Upon the evolution of nitrogen, the reaction mixture was filtered from minor solid impurities and the solvents were removed under reduced pressure (10 Torr) at 20 S. The residue was washed with n-hexane (30 mL) and filtered off to afford 4b as light beige powder. Yield 0.94 g (85percent), mp 215 S (lit.20 mp 214 C); Rf 0.61 (Silica gel, CH2Cl2/MeOH (19:1)). The 1H NMR spectrum corresponds to reported data.
Reference: [1] Tetrahedron, 2015, vol. 71, # 45, p. 8551 - 8556
  • 18
  • [ 6813-38-3 ]
  • [ 99970-84-0 ]
Reference: [1] Tetrahedron Letters, 1990, vol. 31, # 35, p. 5069 - 5072
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
  • 19
  • [ 6813-38-3 ]
  • [ 109073-77-0 ]
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[3] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 2, p. 163 - 165
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