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[ CAS No. 1668-53-7 ] {[proInfo.proName]}

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Chemical Structure| 1668-53-7
Chemical Structure| 1668-53-7
Structure of 1668-53-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1668-53-7 ]

CAS No. :1668-53-7 MDL No. :MFCD16251125
Formula : C25H23N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FROCQMFXPIROOK-UHFFFAOYSA-N
M.W : 397.47 Pubchem ID :74276
Synonyms :

Calculated chemistry of [ 1668-53-7 ]

Physicochemical Properties

Num. heavy atoms : 30
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.16
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 120.04
TPSA : 79.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.07
Log Po/w (XLOGP3) : 5.71
Log Po/w (WLOGP) : 5.52
Log Po/w (MLOGP) : 3.68
Log Po/w (SILICOS-IT) : 6.03
Consensus Log Po/w : 5.0

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.3
Solubility : 0.000201 mg/ml ; 0.000000506 mol/l
Class : Poorly soluble
Log S (Ali) : -7.14
Solubility : 0.0000289 mg/ml ; 0.0000000727 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.15
Solubility : 0.000000279 mg/ml ; 0.0000000007 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.02

Safety of [ 1668-53-7 ]

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

Application In Synthesis of [ 1668-53-7 ]

* 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 [ 1668-53-7 ]
  • Downstream synthetic route of [ 1668-53-7 ]

[ 1668-53-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1237-53-2 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
YieldReaction ConditionsOperation in experiment
79%
Stage #1: With aluminum (III) chloride In chlorobenzene at 25℃; for 0.5 h; Inert atmosphere
Stage #2: at 85℃; for 5 h;
General procedure: To astirred anhydrous chlorobenzene (15 mL) under dry N2 protectionin a 50mL three-necked flask were added 5 (1.6mmol)and anhydrous AlCl3 (0.32 g, 2.4 mmol),the mixture wasstirred for 0.5 h at 25 °C. Then resorcinol (0.24 g, 2.2 mmol)was added, and the mixture was stirred for 5 h at 85 °C. Aftercooling to room temperature, ice water (10 mL) was addedslowly and then chlorobenzene was evaporated under reducedpressure. The mixture was filtered and washed with water(3 × 10 mL), the filter cake was recrystallized with EtOA togive the corresponding products 8a, 8e 9a-9d.
Reference: [1] Journal of Fluorescence, 2018, vol. 28, # 2, p. 707 - 723
[2] Patent: US6242598, 2001, B1,
  • 2
  • [ 242143-64-2 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
YieldReaction ConditionsOperation in experiment
62% With methanesulfonic acid In methanol; m-xylene EXAMPLE 4
4,6-Bis-(2,4-dimethylphenyl)-2-(2,4-dihydroxyphenyl)-s-triazine
To a 500 mL four-necked, round-bottomed flask fitted with a mechanical stirrer, a nitrogen atmosphere and an oil bath are added 20.0 g (0.0524 mol) of the product of Example 2, 23.0 g (0.209 mol) of resorcinol. 7.6 g (0.079 mol) of methanesulfonic acid and 25 mL of m-xylene.
The mixture is stirred at 120° C. for 20 hours and then allowed to cool to room temperature.
A 200 mL portion of heptane and 200 g of ice are added.
The contents are warmed to 55° C. and then allowed to cool to below 40° C.
The crude solid formed is isolated by filtration, washed with water and heptane and then dried under reduced pressure to yield 17.5 g of yellow-orange crude product.
The material is ground in a mortar, taken up in 170 mL of methanol, cooled to -20° C. and then filtered to afford 12.8 g (62percent yield) of the title compound as a yellow solid melting at 203-205° C.
62% With hydrogenchloride In n-heptane; m-xylene EXAMPLE 6
4,6-Bis-(2,4-dimethylphenyl)-2-(2,4-dihydroxyphenyl)-s-triazine
To a 250 mL round-bottomed flask fitted with a magnetic stirrer, a condenser and a nitrogen atmosphere are charged 7.85 g (0.0206 mol) of the product of Example 2, 13.5 g (0.123 mol) of resorcinol, 4 mL of m-xylene and 0.954 g (7.16 mmol) of aluminum chloride.
The mixture is heated to 150° C. for 13.5 hours and then allowed to cool to 90° C.
Portions of 2N hydrochloric acid and heptane are added and the mixture is stirred at 90° C. for 30 minutes followed by stirring for 18 hours at room temperature.
The mixture is then warmed to 35° C.
The crude solid formed is collected by vacuum filtration and is washed with portions of water and heptane.
The solid is then recrystallized twice from methanol to afford 4.76 g (62percent yield) of the title compound as a yellow solid melting at 194-196° C.
Reference: [1] Patent: US6242598, 2001, B1,
[2] Patent: US6242598, 2001, B1,
[3] Patent: US6242598, 2001, B1,
[4] Patent: US6242598, 2001, B1,
  • 3
  • [ 108-77-0 ]
  • [ 108-38-3 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With hydrogenchloride; aluminum (III) chloride In water; chlorobenzene at 20℃; for 1 h; Cooling with ice
Stage #2: at 90℃; for 2 h;
In a 5-liter three-necked flask equipped with mechanical stirring, 3 liters of chlorobenzene, 184 grams of cyanuric chloride, 212 grams of m-xylene were added(2 times the amount) and 400 g of aluminum trichloride (3 times the amount); under ice-cooling, 20 ml of concentrated hydrochloric acid (0.2 times) was added, the reaction was stirred for 1 hour, and the temperature was raised to room temperature and 121 g of resorcinol was added ( 1.1 times) and then heated to 90°C for 2 hours. After the reaction was completed, the reaction solution was slowly added to 5 liters of 10percent hydrochloric acid with stirring, and the precipitated solid was filtered and washed with water.Recrystallization yielded 365 g (yield 92percent) of 2,4-bis(m-xylyl)-6-(1-m-xylenol)-1,3,5-triazine product.
Reference: [1] Patent: CN107746389, 2018, A, . Location in patent: Paragraph 0034; 0035; 0036; 0037; 0038; 0039; 0051; 0052
  • 4
  • [ 126-33-0 ]
  • [ 242143-64-2 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
YieldReaction ConditionsOperation in experiment
69% With hydrogenchloride In ethyl acetate EXAMPLE 7
4,6-Bis-(2,4-dimethylphenyl)-2-(2,4-dihydroxyphenyl)-s-triazine
To a 250 mL round-bottomed flask equipped with a magnetic stirrer, a condenser and a nitrogen atmosphere are added 6.00 g (0.0157 mol) of the product of Example 2, 2.08 g (0.0189 mol) of resorcinol, 2.09 g (0.0157 mol) of aluminum chloride and 6 mL of tetramethylene sulfone (sulfolane).
The mixture is stirred at 138° C. for six hours, 147° C. for seven hours, 160° C. for 10.5 hours and then allowed to cool to room temperature.
A portion of 2N hydrochloric acid is added and the mixture is refluxed for two hours and then allowed to cool to room temperature.
The solids formed are collected by vacuum filtration and then washed with portions of water and heptane.
The crude solid is taken up in ethyl acetate and passed through a plug of silica gel.
The solvent is removed under reduced pressure to give 5.25 g of crude product.
The crude product is recrystallized from methanol to afford 4.29 g (69percent yield) of the title compound as a yellow solid melting at 199-201° C.
Reference: [1] Patent: US6242598, 2001, B1,
  • 5
  • [ 108-77-0 ]
  • [ 95-50-1 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
Reference: [1] Patent: US2003/13879, 2003, A1,
  • 6
  • [ 108-77-0 ]
  • [ 25023-99-8 ]
  • [ 108-46-3 ]
  • [ 1668-53-7 ]
Reference: [1] Patent: US6225468, 2001, B1,
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