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Chemical Structure| 1802-30-8
Chemical Structure| 1802-30-8
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Product Details of [ 1802-30-8 ]

CAS No. :1802-30-8 MDL No. :MFCD01318320
Formula : C12H8N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :KVQMUHHSWICEIH-UHFFFAOYSA-N
M.W : 244.20 Pubchem ID :192744
Synonyms :
2,2’-Bipyridine-5,5’-dicarboxylic Acid;PD 086195;2,2’-Bipyridine-5,5’-dicarboxylate

Calculated chemistry of [ 1802-30-8 ]

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) : 1.19
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 : 0.7

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 : 1.95

Safety of [ 1802-30-8 ]

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 [ 1802-30-8 ]

* 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 [ 1802-30-8 ]
  • Downstream synthetic route of [ 1802-30-8 ]

[ 1802-30-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1762-34-1 ]
  • [ 1802-30-8 ]
YieldReaction ConditionsOperation in experiment
74% Reflux To 5,5'-dimethyl-2,2'-bipyridine (1.0 g) in water (35 ml), KMnO4 (6.0 g) was added and then, the resultant mixture was refluxed with magnetic stirring for overnight. After TLC analyses showed total consumption of the starting materials, the reaction mixture was filtered to remove MnO2 and the filtrate was concentrated to ca. 5 ml. The resultant mixture was then acidified with 35percent HCl aq to be kept in a refrigerator for overnight. The white precipitate was retrieved through filtration and then washed repeatedly with water to give the title compound (1.0 g, 74percent) as a white powder
54% With potassium permanganate In water at 80 - 85℃; for 24 h; A suspension of 5,5′-dimethyl-2,2′-bpy (1.51g, 8.2mmol) was dissolved in 100mL water. Solid KMnO4 (8.57g, 54.2mmol) was added to the initial suspension. Then, the reaction mixture was stirred and heated up to 80–85°C for 24h. The deep black solution was cooled to r.t. and filtered off using frit funnel; the aqueous phase was then neutralized with concentrated HCl, resulting in the formation of white suspension. The solid was then filtered under vacuum. The white powder was collected and dried in vacuum desiccators. Yield: 1.33g, 54percent. 1H NMR (600MHz, [D6] DMSO): δ=9.29 (s, 2H, 6,6′-bpy), 8.57 (m, 2H, 3,3′-bpy), 8.45 (m, 2H, 4,4′-bpy).
Reference: [1] Dalton Transactions, 2008, # 15, p. 2054 - 2060
[2] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[3] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[4] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
[5] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
[6] Molecular Crystals and Liquid Crystals, 2010, vol. 519, p. 43 - 53
[7] Dalton Transactions, 2016, vol. 45, # 10, p. 4407 - 4415
[8] Journal of Materials Chemistry A, 2016, vol. 4, # 40, p. 15320 - 15326
[9] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
[10] Chemical Communications, 2009, # 41, p. 6237 - 6239
[11] Langmuir, 2012, vol. 28, # 11, p. 5023 - 5030
[12] Synlett, 2013, vol. 24, # 6, p. 765 - 769
[13] Tetrahedron, 2016, vol. 72, # 35, p. 5456 - 5464
[14] Chemistry - A European Journal, 1998, vol. 4, # 11, p. 2237 - 2250
[15] Tetrahedron Letters, 1998, vol. 39, # 22, p. 3689 - 3692
[16] European Journal of Organic Chemistry, 1999, # 7, p. 1745 - 1748
[17] Journal of the American Chemical Society, 2013, vol. 135, # 36, p. 13558 - 13566
[18] Chemistry of Materials, 2017, vol. 29, # 8, p. 3671 - 3677
[19] Tetrahedron Letters, 2011, vol. 52, # 9, p. 995 - 998
[20] Inorganica Chimica Acta, 2018, vol. 473, p. 245 - 254
[21] Gazzetta Chimica Italiana, 1997, vol. 127, # 2, p. 63 - 68
[22] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
[23] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
[24] Journal of Organometallic Chemistry, 1988, vol. 355, p. 193 - 196
[25] Tetrahedron Letters, 1995, vol. 36, # 36, p. 6471 - 6474
[26] European Journal of Inorganic Chemistry, 1999, # 9, p. 1507 - 1521
[27] Patent: US2007/290199, 2007, A1,
[28] Dalton Transactions, 2008, # 28, p. 3701 - 3708
[29] Chemistry - A European Journal, 2012, vol. 18, # 1, p. 267 - 276
[30] Organometallics, 2011, vol. 30, # 24, p. 6572 - 6586
[31] Chemical Science, 2013, vol. 4, # 12, p. 4486 - 4493
[32] Chemical Communications, 2014, vol. 50, # 18, p. 2304 - 2307
[33] European Journal of Inorganic Chemistry, 2014, # 12, p. 2029 - 2037
[34] European Journal of Inorganic Chemistry, 2014, vol. 2014, # 12, p. 2029 - 2037
[35] Journal of Organic Chemistry, 2014, vol. 79, # 22, p. 11170 - 11178
[36] Chemistry - A European Journal, 2018, vol. 24, # 54, p. 14539 - 14546
  • 2
  • [ 5326-23-8 ]
  • [ 1802-30-8 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride; sodium hydroxide In methanol; water Example 2
25 g of 6-chloronicotinic acid and 14 g of sodium hydroxide are dissolved in a mixture of 100 ml of water and 80 ml of methanol.
Following the addition of 5 g of palladium (10percent by weight on activated carbon) as catalyst, the mixture is stirred for 24 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-5,5'-dicarboxylic acid, precipitates out as a white solid.
This gives 16.3 g (84percent yield).
81% With hydrogenchloride; sodium hydroxide In water; ethylene glycol Example 1
25 g of 6-chloronicotinic acid and 14 g of sodium hydroxide are dissolved in a mixture of 100 ml of water and 80 ml of ethylene glycol.
Following the addition of 0.56 g of palladium (30percent by weight on activated carbon; corresponds to an addition of 168 mg of pure palladium) as catalyst, the mixture is stirred for 5 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-5,5'-dicarboxylic acid, precipitates out as a white solid.
This gives 15.7 g (81percent yield).
79% With hydrogenchloride; sodium hydroxide In methanol; water Example 3
25 g of 6-chloronicotinic acid and 14 g of sodium hydroxide are dissolved in a mixture of 100 ml of water and 80 ml of methanol.
Following the addition of 10 g of palladium (5percent by weight on activated carbon) as catalyst, the mixture is stirred for 30 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-5,5'-dicarboxylic acid, precipitates out as a white solid.
This gives 15.3 g (79percent yield).
Reference: [1] Patent: US6500956, 2002, B1,
[2] Patent: US6500956, 2002, B1,
[3] Patent: US6500956, 2002, B1,
  • 3
  • [ 108-99-6 ]
  • [ 1802-30-8 ]
Reference: [1] Journal of Organometallic Chemistry, 1988, vol. 355, p. 193 - 196
[2] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 4
  • [ 1762-46-5 ]
  • [ 1802-30-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
  • 5
  • [ 3510-66-5 ]
  • [ 1802-30-8 ]
Reference: [1] Chemistry - A European Journal, 1998, vol. 4, # 11, p. 2237 - 2250
[2] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 6
  • [ 1603-41-4 ]
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 7
  • [ 1003-68-5 ]
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Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 8
  • [ 115185-81-4 ]
  • [ 1802-30-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 9
  • [ 3060-42-2 ]
  • [ 1802-30-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 10
  • [ 1762-34-1 ]
  • [ 244303-60-4 ]
  • [ 1802-30-8 ]
Reference: [1] Patent: JP2005/82511, 2005, A, . Location in patent: Page/Page column 4-6
  • 11
  • [ 59-67-6 ]
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Reference: [1] Journal of the Chemical Society, 1956, p. 616,619
  • 12
  • [ 244303-60-4 ]
  • [ 1802-30-8 ]
Reference: [1] Patent: JP2005/82511, 2005, A, . Location in patent: Page/Page column 5
  • 13
  • [ 64-17-5 ]
  • [ 1802-30-8 ]
  • [ 1762-46-5 ]
YieldReaction ConditionsOperation in experiment
77% at 0℃; for 24 h; Reflux Diethyl 2,2'-bipyridine-5,5'-dicarboxylate
Procedure:
Bipy55'DC (200 mg, 0.82 mmoles) and EtOH (13 mL) were added to a dried flask and stirred on ice.
Thionyl chloride (1.3 mL) was added dropwise on ice, after which the flask was fitted with a reflux condenser and heated at reflux.
After 24 hr, the reaction was cooled on ice and quenched by the dropwise addition of saturated Na2CO3 (20 mL).
The aqueous layer was extracted with CH2Cl2 (4*20 mL) and the combined organics were dried over Na2SO4(s), and concentrated under reduced pressure.
The crude product was then purified by chromatography on silica (3percent acetone in 1:1 DCM/hexanes) to afford the title compound (190 mg, 77percent) as a white solid. 1H NMR (500 MHz, CDCl3) δ 9.32 (dd, J=0.5, 2.0 Hz, 1H), 8.59 (dd, J=0.5, 8.5 Hz, 1H), 8.46 (dd, J=2.0, 8.5 Hz, 1H), 4.47 (q, J=7.5 Hz, 2H), 1.46 (t, J=7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [calc'd for C16H17N2O4 (M+H)+ 301.1183].
Reference: [1] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[2] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[3] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
[4] Chemical Communications, 2016, vol. 52, # 48, p. 7600 - 7603
[5] Journal of the American Chemical Society, 2017, vol. 139, # 49, p. 17747 - 17750
[6] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2457 - 2465
[7] Chemistry - A European Journal, 2018,
[8] Patent: US2016/280701, 2016, A1, . Location in patent: Paragraph 0300; 0301; 0302
[9] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[10] Journal of Molecular Catalysis A: Chemical, 2010, vol. 331, # 1-2, p. 117 - 124
[11] European Journal of Inorganic Chemistry, 1999, # 9, p. 1507 - 1521
[12] Chemical Communications, 2009, # 41, p. 6237 - 6239
[13] Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 191,193
[14] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
[15] Dalton Transactions, 2008, # 28, p. 3701 - 3708
[16] Physical Chemistry Chemical Physics, 2014, vol. 16, # 28, p. 14874 - 14881
[17] Patent: CN106496113, 2017, A, . Location in patent: Paragraph 0059; 0060; 0066; 0067; 0073; 0074
  • 14
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
  • 15
  • [ 64-17-5 ]
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  • [ 1762-46-5 ]
  • [ 105501-69-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
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