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[ CAS No. 16063-70-0 ] {[proInfo.proName]}

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Chemical Structure| 16063-70-0
Chemical Structure| 16063-70-0
Structure of 16063-70-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16063-70-0 ]

CAS No. :16063-70-0 MDL No. :MFCD00043007
Formula : C5H2Cl3N Boiling Point : -
Linear Structure Formula :- InChI Key :CNLIIAKAAMFCJG-UHFFFAOYSA-N
M.W : 182.44 Pubchem ID :27666
Synonyms :

Calculated chemistry of [ 16063-70-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.27
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) : -5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 3.04
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 3.35
Consensus Log Po/w : 2.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.42
Solubility : 0.0688 mg/ml ; 0.000377 mol/l
Class : Soluble
Log S (Ali) : -3.05
Solubility : 0.163 mg/ml ; 0.000893 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.87
Solubility : 0.0245 mg/ml ; 0.000134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 16063-70-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16063-70-0 ]

* 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 [ 16063-70-0 ]
  • Downstream synthetic route of [ 16063-70-0 ]

[ 16063-70-0 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2176-62-7 ]
  • [ 6515-09-9 ]
  • [ 16063-70-0 ]
  • [ 2402-79-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 493 - 496
  • 2
  • [ 16063-70-0 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 3
  • [ 16063-70-0 ]
  • [ 7664-41-7 ]
  • [ 4214-74-8 ]
Reference: [1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
  • 4
  • [ 16063-70-0 ]
  • [ 124-41-4 ]
  • [ 13472-58-7 ]
Reference: [1] Journal of the Chemical Society [Section] B: Physical Organic, 1966, p. 991,992
  • 5
  • [ 16063-70-0 ]
  • [ 40360-44-9 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 23, p. 4533 - 4536
  • 6
  • [ 16063-70-0 ]
  • [ 823-56-3 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 23, p. 4533 - 4536
  • 7
  • [ 16063-70-0 ]
  • [ 23906-97-0 ]
  • [ 823-56-3 ]
  • [ 89402-43-7 ]
Reference: [1] Patent: US5468863, 1995, A,
  • 8
  • [ 16063-70-0 ]
  • [ 823-56-3 ]
  • [ 89402-43-7 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 23, p. 4301 - 4311
  • 9
  • [ 16063-70-0 ]
  • [ 14482-51-0 ]
YieldReaction ConditionsOperation in experiment
99% With trimethylsilyl bromide In propiononitrile at 100℃; for 14 h; 2-bromo-3,5-dichloropyridine. A 100 mL round-bottom flask equipped with a condenser was charged with 1.82 g of compound 71 (10.0 mmol) and propiononitrile (20 mL), 3.06 g TMSBr (20.0 mmol) was slowly added to the above solution. The reaction mixture was stirred at 1000C under nitrogen for 14 hrs, then cooled to a temperature of about 250C and diluted with EtOAc (100 mL). The EtOAc layer was isolated, dried, and concentrated under reduced pressure to provide 72 as a yellowish solid (>99percent yield).
Reference: [1] Patent: WO2008/132600, 2008, A2, . Location in patent: Page/Page column 269
  • 10
  • [ 16063-70-0 ]
  • [ 89402-43-7 ]
YieldReaction ConditionsOperation in experiment
90% With potassium fluoride; 18-crown-6 ether; potassium carbonate; cesium fluoride In sulfolane; dimethyl sulfoxide at 120 - 200℃; for 3 h; 400 g of sulfolane and 400 g of dimethylsulfoxide were weighed into a 1000 mL flask and dehydrated to a temperature of less than 0.05percent at 200 ° C under a pressure of 0.07 MPa (negative pressure)96 g (1.66 mol) of cesium fluoride, 96 g (1.66 mol) of potassium fluoride, 120 g (0.67 mol) of trichloropyridine, 2 g of 18-crown ether and 3 g of potassium carbonate were weighed into a reaction flask at 120 ° C and heated to 200 ° C The product was collected in about 3 hours. 95 g (0.51 mol) of the product was obtained in 90percent yield. The purity was 96.8percent as determined by gas chromatography.
Reference: [1] Patent: CN106008329, 2016, A, . Location in patent: Paragraph 0008; 0009
[2] Synthetic Communications, 2004, vol. 34, # 23, p. 4301 - 4311
[3] Patent: US33478, 1990, E1,
[4] Patent: US4565568, 1986, A,
[5] Patent: US4678509, 1987, A,
  • 11
  • [ 16063-70-0 ]
  • [ 23906-97-0 ]
  • [ 823-56-3 ]
  • [ 89402-43-7 ]
Reference: [1] Patent: US5468863, 1995, A,
  • 12
  • [ 16063-70-0 ]
  • [ 823-56-3 ]
  • [ 89402-43-7 ]
Reference: [1] Synthetic Communications, 2004, vol. 34, # 23, p. 4301 - 4311
  • 13
  • [ 16063-70-0 ]
  • [ 85331-33-5 ]
YieldReaction ConditionsOperation in experiment
40% With copper(I) cyanide; tetraphenylphosphonium bromide; potassium iodide In diethylene glycol dimethyl ether for 113 h; Heating / reflux [0169] In analogy to Troschuetz, R. et al., J. Heterocycl. Chem. 33, 1815-1821 (1996), 150 ml of diethylene glycol dimethyl ether, 47.68 g (0.261 mol) of 2,3,5-trichloro-pyridine, 2.0 g (0.005 mol) of tetraphenylphosphonium bromide, 4.0 g (0.024 mol) of finely powdered potassium iodide and 75.0 g (0.838 mol) of copper(I) cyanide are mixed under nitrogen and stirred under reflux for 24 hours. Then a further 100 ml of diethylene glycol dimethyl ether, 2.0 g (0.005 mol) of tetraphenylphosphonium bromide, 4.0 g (0.024 mol) of finely powdered potassium iodide and 75 g (0.838 mol) of copper(I) cyanide are added, and the mixture is stirred at reflux temperature for a further 89 hours. Cooling to room temperature is followed by filtration with suction, and the filtrate is distilled to remove most of the diethylene glycol dimethyl ether. The residue is taken up in toluene and washed with an aqueous solution of Mohr's salt and then with aqueous NaHCO3 solution (peroxide test). It is then washed with water to remove diethylene glycol dimethyl ether. After filtration through cellit, the filtrate is dried over magnesium sulfate, and the solution is concentrated. [0170] 18.0 g (40.0percent) of 2-cyano-3,5-dichloropyridine are obtained.
Reference: [1] Patent: US2003/232842, 2003, A1, . Location in patent: Page 8
  • 14
  • [ 16063-70-0 ]
  • [ 406676-24-2 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 23, p. 4533 - 4536
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