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[ CAS No. 22282-65-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22282-65-1
Chemical Structure| 22282-65-1
Chemical Structure| 22282-65-1
Structure of 22282-65-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 22282-65-1 ]

CAS No. :22282-65-1 MDL No. :MFCD09702484
Formula : C6H6IN Boiling Point : -
Linear Structure Formula :- InChI Key :RZRJLVROVUWDKL-UHFFFAOYSA-N
M.W : 219.02 Pubchem ID :12691322
Synonyms :

Calculated chemistry of [ 22282-65-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.92
TPSA : 12.89 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 2.82
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.95
Solubility : 0.246 mg/ml ; 0.00112 mol/l
Class : Soluble
Log S (Ali) : -1.79
Solubility : 3.52 mg/ml ; 0.0161 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.37
Solubility : 0.0936 mg/ml ; 0.000428 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 22282-65-1 ]

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 [ 22282-65-1 ]

* 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 [ 22282-65-1 ]
  • Downstream synthetic route of [ 22282-65-1 ]

[ 22282-65-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 3678-63-5 ]
  • [ 22282-65-1 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogen iodide; sodium iodide In water at 140℃; for 168 h; 4-Chloropicoline (10 g, 78 mmol), sodium iodide (17.8 g, 118 mmol) and hydroiodic acid (57percent, 26 mL, 196 mmol) were heated in a sealed class tube at 140C for 7 days. The reac- tion mixture was poured into ice water and neutralized by addition of sodium hydroxide. This mixture was extracted three times with dichloromethane (300 mL each). The com- bined organic extracts were dried with magnesium sulfate, filtered and evaporated. The desired product was obtained as an off-white solid (14.7 g, 85percent) and used without any further purification for the next step.
Reference: [1] Patent: WO2004/80998, 2004, A1, . Location in patent: Page 27
[2] Patent: US2002/40040, 2002, A1,
[3] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 5, p. 1731 - 1737
  • 2
  • [ 22282-99-1 ]
  • [ 22282-65-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266[2] Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4
  • 3
  • [ 565237-08-3 ]
  • [ 75-36-5 ]
  • [ 22282-65-1 ]
  • [ 565237-07-2 ]
YieldReaction ConditionsOperation in experiment
22% With sodium iodide In acetonitrile for 33 h; Heating / reflux 4-Iodo-2-methylpyridine and (4-IODO-2-PYRIDYL) methylacetate : 2- ( ( (TETT-BUTYLDIMETHYLSILYL) OXY) METHYL)-4-CHLOROPYRIDINE (600 mg, 2.33 MMOL), dry sodium iodide (5 g) and freshly distilled acetyl chloride (0. 7. mL, 9.78 MMOL) in 6 mL of anhydrous ACETONITRILE were REFLUXED under nitrogen for 33 hours. Aqueous 10percent K2CO3/5percent NAHSO3 was added and the mixture extracted three times with chloroform. After drying (NA2SO4) and evaporation of the chloroform, flash chromatography (hexane/EtOAc 9 : 1) yielded 110 mg (22percent) of 4-Iodo-2- METHYLPYRIDINE as a white solid and 290 mg (45percent) of (4-iodo-2-pyridyl) methylacetate as a white solid. 4-Iodo-2-methypyridine: 1H NMR (CHO) 8 8.06 (d, LH, *5. 2 Hz, H-6); 7.48 (d, 1H, J=1.1 Hz, H- 3); 7.38 (dd, 1H, J1=5. 2, 1. 4 Hz, H-5); 2.41 (s, 3H, CH3) ;13C NMR (CDCl3) 8 159.8 (C-2), 149.8 (C-6), 133.0 (C-3), 130.4 (C-5), 106.3 (C-4), 24.5 (CH3). (4-iodo-2-pyridyl) METHYLACETATE : 1H NMR (CDCl3) 8 8.16 (d, 1H, J=5. 2 Hz, H-6); 7.66 (d, LH, J=1. 0 Hz, H-3); 7.54 (dd, 1H, J1=5. 2,. J2=1. 6 Hz, H-5); 5.09 (s, 2H, CH2) ; 2.11 (s, 3H, CH3) ; 13C NMR (CDCTS) 8 170.9 (CO), 157.1 (C-2), 150.1 (C-6), 132.5 (C-3), 131.3 (C-5), 106.6 (C-4), 66.3 (CH2), 21.3 (CH3).
Reference: [1] Patent: WO2005/12323, 2005, A2, . Location in patent: Page/Page column 45
  • 4
  • [ 79534-90-0 ]
  • [ 22282-65-1 ]
Reference: [1] Heterocycles, 1981, vol. 16, # 7, p. 1161 - 1164
  • 5
  • [ 1121-76-2 ]
  • [ 22282-65-1 ]
Reference: [1] Patent: WO2005/12323, 2005, A2,
  • 6
  • [ 63071-10-3 ]
  • [ 22282-65-1 ]
Reference: [1] Patent: WO2005/12323, 2005, A2,
  • 7
  • [ 18437-58-6 ]
  • [ 22282-65-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1959, vol. <4> 9, p. 164,172
[2] Roczniki Chemii, 1959, vol. 33, p. 387,392[3] Chem.Abstr., 1959, p. 18954
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