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[ CAS No. 843663-18-3 ] {[proInfo.proName]}

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Chemical Structure| 843663-18-3
Chemical Structure| 843663-18-3
Structure of 843663-18-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 843663-18-3 ]

CAS No. :843663-18-3 MDL No. :MFCD03411549
Formula : C7H5BFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DECWLXUOZUMPBF-UHFFFAOYSA-N
M.W : 164.93 Pubchem ID :2783130
Synonyms :

Calculated chemistry of [ 843663-18-3 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.94
TPSA : 64.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.65
Log Po/w (WLOGP) : -0.2
Log Po/w (MLOGP) : 0.08
Log Po/w (SILICOS-IT) : -0.34
Consensus Log Po/w : 0.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.58
Solubility : 4.38 mg/ml ; 0.0265 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 4.39 mg/ml ; 0.0266 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.65
Solubility : 3.74 mg/ml ; 0.0226 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.02

Safety of [ 843663-18-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 843663-18-3 ]

* 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 [ 843663-18-3 ]
  • Downstream synthetic route of [ 843663-18-3 ]

[ 843663-18-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 843663-18-3 ]
  • [ 137553-42-5 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 103, p. 84910 - 84919
  • 2
  • [ 121-43-7 ]
  • [ 105942-08-3 ]
  • [ 843663-18-3 ]
Reference: [1] Patent: US2009/291956, 2009, A1, . Location in patent: Page/Page column 25; 26
  • 3
  • [ 5419-55-6 ]
  • [ 105942-08-3 ]
  • [ 843663-18-3 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane; toluene at -75 - -74℃; for 2.25 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; toluene at -20 - 20℃;
Dissolve 2-Fluoro-4-bromobenzonitrile (200 g, 990 mmol, 1.00 eq.) and triisopropyl borate (228 g, 1188 mmol, 1.2 eq.) in 700 mL of THF and 1400 mL of toluene. Cool the mixture with a dry ice/acetone bath to an internal temperature of -75 0C. Slowly add n-BuLi (396 mL of a 2.5 M solution in hexanes) over a period of 2 hours. After addition is complete, a light-red, thin slurry occurs. Let the solution stir at -74 0C for 15 minutes, allow the solution to warm to -20 0C and then quench with 1500 mL of 2.5 M HCl. Let the solution warm to RT. Separate layers, extract the aqueous layer with EtOAc, dry the combined organic phases with Na2SQ,), filter and concentrate in vacuo to yield a light-brown solid.Triturate the solid with hexane and transfer to a scintered glass funnel. Rinse with hexane one more time to obtain a pale-yellow filtrate. Stir the light-brown solid with cold CH2Cl2 and filter. Rinse with a small volume of CH2Cl2 to yield an off-white solid and a brown filtrate. Dry the solid in a vacuum oven at 40 0C and dried to yield 112g (679 mmol, 69percent) of 3-fluoro-4-cyanophenylboronic acid as an off-white solid.
Reference: [1] Patent: WO2007/87488, 2007, A2, . Location in patent: Page/Page column 17; 47-48
  • 4
  • [ 105942-08-3 ]
  • [ 843663-18-3 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 2, p. 305 - 307
  • 5
  • [ 843663-18-3 ]
  • [ 76-09-5 ]
  • [ 870238-67-8 ]
YieldReaction ConditionsOperation in experiment
85.6% at 20 - 40℃; Step 2.
A suspension of the crude 3-fluoro-4-cyanophenyl boronic acid (9.2 Kg, 55.8 mol) in cyclohexane (150 L) was treated with pinacol (13.2 Kg, 111.6 mol, 2.0 equiv) at room temperature, and the resulting reaction mixture was warmed to 40° C. for 4 h.
When TLC and LC/MS showed that the reaction was deemed complete, the reaction mixture was cooled down to room temperature before being washed with water (2*75 L).
The organic layer was then dried over magnesium sulfate (MgSO4) and concentrated under the reduced pressure to afford 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (19, 11.8 Kg, 13.8 Kg theoretical, 85.6percent yield) as a light yellow solid.
Reference: [1] Patent: US2009/291956, 2009, A1, . Location in patent: Page/Page column 25; 26
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