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[ CAS No. 53581-86-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 53581-86-5
Chemical Structure| 53581-86-5
Chemical Structure| 53581-86-5
Structure of 53581-86-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53581-86-5 ]

CAS No. :53581-86-5 MDL No. :MFCD08703355
Formula : C8H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IVBZHFWJBYTRNG-UHFFFAOYSA-N
M.W : 170.59 Pubchem ID :13865115
Synonyms :

Calculated chemistry of [ 53581-86-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.33
TPSA : 26.3 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) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.02
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 2.61
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.79
Solubility : 0.278 mg/ml ; 0.00163 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.289 mg/ml ; 0.0017 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.141 mg/ml ; 0.000824 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 53581-86-5 ]

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

Application In Synthesis of [ 53581-86-5 ]

* 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 [ 53581-86-5 ]
  • Downstream synthetic route of [ 53581-86-5 ]

[ 53581-86-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 53581-86-5 ]
  • [ 2420-26-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 24, p. 8206 - 8220
[2] ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78
  • 2
  • [ 53581-86-5 ]
  • [ 57479-70-6 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 1741
  • 3
  • [ 90296-27-8 ]
  • [ 53581-86-5 ]
Reference: [1] ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 24, p. 8206 - 8220
[3] Patent: WO2006/78676, 2006, A2, . Location in patent: Page/Page column 43; 44
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6463 - 6466
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 419 - 434
  • 4
  • [ 61072-56-8 ]
  • [ 124-41-4 ]
  • [ 53581-86-5 ]
YieldReaction ConditionsOperation in experiment
77.5% at 50℃; for 3 h; 4-Chloro-2-Fluorobenzaldehyde (300 mg, 1.89 mmol) was diluted with NaOMe (3784 μL, 1.89 mmol) (solution in methanol), heated to 500C and stirred for 3 hours. The reaction was concentrated in half and loaded directly onto a biotage 25 cartridge eluting with 5percent ethyl acetate/hexanes to yield 4-chloro-2-methoxybenzaldehyde (250 mg, 1.47 mmol, 77.5 percent yield).
Reference: [1] Patent: WO2009/158426, 2009, A1, . Location in patent: Page/Page column 140
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5037 - 5041[3] Angew. Chem., 2018, vol. 130, # 18, p. 5131 - 5135,5
  • 5
  • [ 67-56-1 ]
  • [ 874-42-0 ]
  • [ 53581-86-5 ]
YieldReaction ConditionsOperation in experiment
51% at 65℃; for 3 h; General procedure: To a stirred solution of substrate (1 mmol, arylhalide/olefinic halide) in suitable alcohol (MeOH/EtOH, 10 mL), sodiumcarbonate (1.06 g, 2 mol percent) was added and the reaction mixture was refluxed(MeOH = 65 C/EtOH = 78 C) for specified time. On completion, the reactionmixture was filtered, washed with methanol and dried in vacuo. The residuewas taken in ethyl acetate (20 mL) and washed with water. Organic layer wasdried over anhydrous sodium sulfate and evaporated in vacuo. The residuethus obtained was purified through Flash chromatography using ethyl acetate–hexane system. All the compounds were characterized and confirmed bycomparison of their spectral data and physical properties with reportedliterature
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 18, p. 2340 - 2344
  • 6
  • [ 174913-09-8 ]
  • [ 68-12-2 ]
  • [ 53581-86-5 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3630 - 3633
  • 7
  • [ 114615-82-6 ]
  • [ 90296-27-8 ]
  • [ 53581-86-5 ]
Reference: [1] Patent: EP1104754, 2001, A1,
  • 8
  • [ 2420-26-0 ]
  • [ 77-78-1 ]
  • [ 53581-86-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 260 - 266
[2] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
[3] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
  • 9
  • [ 78955-90-5 ]
  • [ 53581-86-5 ]
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 419 - 434
  • 10
  • [ 57479-70-6 ]
  • [ 53581-86-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1687 - 1700
  • 11
  • [ 5306-98-9 ]
  • [ 53581-86-5 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
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