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[ CAS No. 7153-08-4 ] {[proInfo.proName]}

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Chemical Structure| 7153-08-4
Chemical Structure| 7153-08-4
Structure of 7153-08-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 7153-08-4 ]

CAS No. :7153-08-4 MDL No. :MFCD00023554
Formula : C5H3I2NO Boiling Point : -
Linear Structure Formula :- InChI Key :FRPFEVLOFNAKBS-UHFFFAOYSA-N
M.W : 346.89 Pubchem ID :21752
Synonyms :

Calculated chemistry of [ 7153-08-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.69
TPSA : 33.12 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) : -7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 1.8
Log Po/w (WLOGP) : 2.0
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.62
Solubility : 0.0836 mg/ml ; 0.000241 mol/l
Class : Soluble
Log S (Ali) : -2.11
Solubility : 2.66 mg/ml ; 0.00768 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.31
Solubility : 0.169 mg/ml ; 0.000488 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.17

Safety of [ 7153-08-4 ]

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

Application In Synthesis of [ 7153-08-4 ]

* 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 [ 7153-08-4 ]
  • Downstream synthetic route of [ 7153-08-4 ]

[ 7153-08-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 108-96-3 ]
  • [ 89282-03-1 ]
  • [ 7153-08-4 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
  • 2
  • [ 53710-18-2 ]
  • [ 10034-85-2 ]
  • [ 110-86-1 ]
  • [ 13472-80-5 ]
  • [ 7153-08-4 ]
Reference: [1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
  • 3
  • [ 626-05-1 ]
  • [ 10034-85-2 ]
  • [ 110-86-1 ]
  • [ 13472-80-5 ]
  • [ 7153-08-4 ]
Reference: [1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
  • 4
  • [ 108-96-3 ]
  • [ 7153-08-4 ]
YieldReaction ConditionsOperation in experiment
95% With N-iodo-succinimide In acetonitrile for 3 h; Reflux I Oa. 3,5-Diiodo-pyridin-4-ol Into a 3 L three necked round bottom flask I ,4-dihydropyridin-4-one (50.0 g, 0.50 mol) and N-iodosuccinimide (232 g, 1.00 mmol) were suspended inacetonitrile (1 L). The reaction mixture was refluxed for 3h. The mixture was cooled down with an ice bath and then filtered and washed with acetonitrile (150 mL). The light yellow solid was dried at 60°C under reduced pressure for 15 hr to obtain 165 g (95 percent) of the title compound as a light yellow solid. LC/MS (Method B): Rt 1.34 mm, (M+H) 348.
Reference: [1] Patent: WO2015/144290, 2015, A1, . Location in patent: Page/Page column 69
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1078 - 1101
[3] DRP/DRBP Org.Chem., [4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 20, p. 765
[5] Journal of the Society of Chemical Industry, London, 1943, vol. 62, p. 189
[6] Journal of the Society of Chemical Industry, London, 1946, vol. 65, p. 204
[7] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
[8] Justus Liebigs Annalen der Chemie, 1932, vol. 494, p. 284,300
  • 5
  • [ 626-64-2 ]
  • [ 7153-08-4 ]
YieldReaction ConditionsOperation in experiment
94% With iodine; sodium acetate; sodium hydroxide In water for 0.333333 h; Reflux To a solution of starting material 4-hydroxypyridine (9) (5.01 g, 52.6mmol, 1.0equiv) in H2O (67 mL) was added a solution of NaOH (13.2 g, 330mmol, 6.3 equiv) and NaOAc (40.1 g, 489mmol, 9.3 equiv) in H2O (167 mL). After the solution was stirred and refluxed,powdered I2 (46.9 g, 184mmol, 3.5 equiv) was added to the solution. The solution was then acidified with 50percent AcOH, and neutralized with 40percent NaOH. This acidification neutralization procedure was conducted under reflux and repeated three times in 20min. The forth acidification was made until free iodine was precipitated. After sublimation of the I2 by boiling, the residue was filtered, washed with boiling water, and then dried to give the product 12 as a colorless powder (17.18 g, 49.5mmol, 94percent); mp 280 °C with decomposition; IR (KBr, cm-1): 3166, 2952, 2880, 2805, 2360, 1605, 1525, 1334, 1270, 1038, 846, 746, 712, 597; 1HNMR (300 MHz, DMSO-d6): δ 11.95 (1H, s, OH), 8.27 (2H, s, H2/6); 13CNMR (75 MHz, DMSO-d6): δ 170.52, 143.04, 86.59; ESI-HRMS (m/z) calcd for C5H2I2NO [M-H]- 345.8231, found 345.8231.
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 14, p. 2467 - 2470
[2] Chemical Communications, 2012, vol. 48, # 26, p. 3233 - 3235
[3] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 5, p. 673 - 683
[4] Journal of Materials Chemistry, 2001, vol. 11, # 9, p. 2271 - 2281
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12398 - 12402[6] Angew. Chem., 2016, vol. 128, # 40, p. 12586 - 12590,5
[7] Patent: US6642237, 2003, B1, . Location in patent: Page/Page column 79; 186
  • 6
  • [ 108-96-3 ]
  • [ 89282-03-1 ]
  • [ 7153-08-4 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1956, vol. 289, p. 651,660
  • 7
  • [ 74263-51-7 ]
  • [ 93-97-0 ]
  • [ 7153-08-4 ]
Reference: [1] DRP/DRBP Org.Chem., [2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 2270
  • 8
  • [ 53710-18-2 ]
  • [ 10034-85-2 ]
  • [ 110-86-1 ]
  • [ 13472-80-5 ]
  • [ 7153-08-4 ]
Reference: [1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
  • 9
  • [ 626-05-1 ]
  • [ 10034-85-2 ]
  • [ 110-86-1 ]
  • [ 13472-80-5 ]
  • [ 7153-08-4 ]
Reference: [1] Roczniki Chemii, 1938, vol. 18, p. 96,100[2] Chem. Zentralbl., 1939, vol. 110, # II, p. 643
  • 10
  • [ 13993-58-3 ]
  • [ 64-17-5 ]
  • [ 141-52-6 ]
  • [ 147-93-3 ]
  • [ 7153-08-4 ]
  • [ 119-80-2 ]
Reference: [1] Journal of the American Pharmaceutical Association (1912-1977), 1951, vol. 40, p. 143,144, 149
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