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[ CAS No. 95658-81-4 ] {[proInfo.proName]}

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Chemical Structure| 95658-81-4
Chemical Structure| 95658-81-4
Structure of 95658-81-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 95658-81-4 ]

CAS No. :95658-81-4 MDL No. :MFCD16999137
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :OATUMQZBLZQKBX-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :21949823
Synonyms :

Calculated chemistry of [ 95658-81-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.15
TPSA : 44.02 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 : Yes
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 0.945 mg/ml ; 0.0071 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 0.864 mg/ml ; 0.00649 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.26
Solubility : 0.73 mg/ml ; 0.00548 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 95658-81-4 ]

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 [ 95658-81-4 ]

* 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 [ 95658-81-4 ]
  • Downstream synthetic route of [ 95658-81-4 ]

[ 95658-81-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 473923-98-7 ]
  • [ 95658-81-4 ]
YieldReaction ConditionsOperation in experiment
90% With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; In a 100 mL round bottom flask, 3- methoxy-5-methyl-benzonitrile (500 mg, 3.39 mmol) was dissolved in 15 mL dry DCM, and tetrabutylammonium iodide (1.38 g, 3.73 mmol, 3.5 eq.) was added. The flask was cooled to -78 0C. BCk (1 M in DCM, 11.87 mL, 33.16 mmol) was added to the reaction dropwise. The reaction mixture was stirred at -78 0C and warmed up to room temperature overnight. The reaction mixture was quenched with ice and neutralized with saturated NaHCCh solution. DCM was added to extract the <n="425"/>reaction mixture. The organic layer was concentrated down and purified (silica gel, 0-10percent MeOH/DCM) to give a light yellow solid (408 g, 90percent). LC-MS shows 132.0 (M-I). 1H NMR (300 MHz, CDCb): δ 7.20 (s, 1 H), 6.96 (s, 1 H), 6.91 (s, 1 H), 2.37 (s, 3 H).
77%
Stage #1: With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at 20℃; for 0.5 h;
Stage #2: With water In dichloromethane at 0℃; for 0.333333 h;
BC13 (50 ml, 50 mmol, 1 M in DCM) was added dropwise to a solution of 3-methoxy- 5-methylbenzonitrile (Example 2) (2.101 g, 14.27 mmol) and Bu4NI (5.80 g, 15.7 mmol) in dry DCM (50 ml) AT-78 °C. The cold bath was removed and the mixture stirred at ambient temperature for 30 min. Ice was added and the mixture stirred 20 min, and neutralized with sat. NAHCO3. ORGANIC layer separated and product isolated by flash chromatography using 1- 2percent MeOH in DCM. Yield 1.465 g (77percent), white SOLID,-80percent pure by NMR. IN NMR (400 MHz, CDCl3) 8 2.33 (s, 3 H), 6.89 (s, 1 H), 6.92 (s, 1 H), 7.03 (s, 1 H). 13 NMR (100 MHZ, CDCL3) 8 21.12, 112. 79, 115. 85, 118. 70,121. 19,125. 27,141. 20, 155.81.
Reference: [1] Patent: WO2009/5674, 2009, A2, . Location in patent: Page/Page column 423; 424
[2] Patent: WO2004/63156, 2004, A1, . Location in patent: Page 31
  • 2
  • [ 124289-21-0 ]
  • [ 95658-81-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[2] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
  • 3
  • [ 872286-49-2 ]
  • [ 95658-81-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
  • 4
  • [ 585-81-9 ]
  • [ 95658-81-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
  • 5
  • [ 26613-67-2 ]
  • [ 95658-81-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 885,889
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