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[ CAS No. 10128-71-9 ] {[proInfo.proName]}

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Chemical Structure| 10128-71-9
Chemical Structure| 10128-71-9
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Product Details of [ 10128-71-9 ]

CAS No. :10128-71-9 MDL No. :MFCD00234165
Formula : C6H5NO3 Boiling Point : -
Linear Structure Formula :NC5H3(OH)COOH InChI Key :JEHGATQUCUYHJL-UHFFFAOYSA-N
M.W : 139.11 Pubchem ID :459503
Synonyms :

Calculated chemistry of [ 10128-71-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 33.22
TPSA : 70.42 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) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.87
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 0.49
Log Po/w (MLOGP) : -1.72
Log Po/w (SILICOS-IT) : 0.27
Consensus Log Po/w : 0.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.44
Solubility : 5.06 mg/ml ; 0.0363 mol/l
Class : Very soluble
Log S (Ali) : -1.62
Solubility : 3.33 mg/ml ; 0.0239 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.8
Solubility : 22.3 mg/ml ; 0.16 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 10128-71-9 ]

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 [ 10128-71-9 ]

* 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 [ 10128-71-9 ]
  • Downstream synthetic route of [ 10128-71-9 ]

[ 10128-71-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 10128-71-9 ]
  • [ 98273-79-1 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 64
  • 2
  • [ 7579-20-6 ]
  • [ 10128-71-9 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With sulfuric acid; sodium nitrite In water at 10 - 80℃;
Stage #2: at 65℃;
Stage #3: With ammonia In water
Step B: 3-Hydroxyisonicotinic acid: 3-Aminoisonicotinic acid (108.86 g, 788.13 mmol) was dissolved in water (1740 mL) then treated with sulfuric acid (84.020 mL, 1576.3 mmol). The yellow slurry was cooled to <10° C. and a solution of sodium nitrite (60.359 g, 874.83 mmol) in water (510 mL) was added dropwise while maintaining the temperature at <10° C. The solution was heated to 80° C., which caused a thick precipitate to form. The suspension was cooled to 65° C. and treated with glacial acetic acid (88 mL, in a continuous pour) followed by concentrated ammonium hydroxide (190 mL) to a final pH of approximately 4.5. The solids were collected by vacuum filtration and washed with cold water. After air-drying 16 hours, a free-flowing granular solid was obtained (99.37 g, 91percent).
88% With sulfuric acid; sodium nitrite In water at 80℃; for 0.25 h; To a suspension of 3-amino-isonicotinic acid (2.1 g, 15.2 mmol) in water (35 ml) was added concentrated sulphuric acid (1.5 ml). The solution was cooled to 50C and vigorously stirred before a solution of sodium nitrite (1.05 g, 15.2 mmol) in water (10 ml) was added. The suspension was slowly heated to 8O0C and held at this temperature for 15 minutes, then cooled to 650C and acetic acid (1.5 ml) was added. The pH of the solution was adjusted to pH 4.5 by the addition of concentrated ammonia solution (approximately 3.5 ml) then the mixture was placed in the refrigerator overnight. The resultant precipitate was collected by filtration, washed with water (20 ml) and dried under vacuum to afford the title compound as a yellow solid (1.85 g, 88percent). IH NMR (d4-Me0H, 400 MHz) 8.37 (s, IH), 8.09 (d, J = 5.5 Hz, IH), 7.81 (d, J = 5.5 Hz, IH).
Reference: [1] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 78; 30
[2] Patent: WO2008/24725, 2008, A1, . Location in patent: Page/Page column 67
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 6942 - 6990
  • 3
  • [ 15031-12-6 ]
  • [ 79-10-7 ]
  • [ 10128-71-9 ]
Reference: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1983, vol. 37, # 2, p. 127 - 132
[2] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 486 - 497
  • 4
  • [ 92404-81-4 ]
  • [ 10128-71-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736
  • 5
  • [ 92404-80-3 ]
  • [ 10128-71-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736
  • 6
  • [ 55-22-1 ]
  • [ 10128-71-9 ]
Reference: [1] Heterocyclic Communications, 2003, vol. 9, # 5, p. 489 - 492
[2] Polish Journal of Chemistry, 2005, vol. 79, # 11, p. 1813 - 1819
[3] Chemische Berichte, 1928, vol. 61, p. 2214
[4] Croatica Chemica Acta, 2010, vol. 83, # 3, p. 291 - 298
  • 7
  • [ 4664-01-1 ]
  • [ 10128-71-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 6942 - 6990
  • 8
  • [ 19539-50-5 ]
  • [ 10128-71-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736
[2] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 725 - 736
  • 9
  • [ 109-00-2 ]
  • [ 124-38-9 ]
  • [ 10128-71-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 1, p. 127 - 135
  • 10
  • [ 88912-27-0 ]
  • [ 10128-71-9 ]
Reference: [1] Chemische Berichte, 1928, vol. 61, p. 2214
  • 11
  • [ 67-56-1 ]
  • [ 10128-71-9 ]
  • [ 10128-72-0 ]
Reference: [1] Journal of Molecular Structure, 2007, vol. 844-845, p. 300 - 307
[2] Tetrahedron, 1958, vol. 3, p. 49,56
[3] Patent: WO2013/102145, 2013, A1, . Location in patent: Paragraph 0159
[4] Patent: US2015/344483, 2015, A1, . Location in patent: Paragraph 0337; 0338
  • 12
  • [ 10128-71-9 ]
  • [ 19539-50-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 549 - 552
  • 13
  • [ 10128-71-9 ]
  • [ 112372-15-3 ]
Reference: [1] Patent: WO2013/127266, 2013, A1,
[2] Patent: WO2013/127267, 2013, A1,
[3] Patent: WO2013/127268, 2013, A1,
[4] Patent: WO2013/130943, 2013, A1,
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