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[ CAS No. 65685-51-0 ] {[proInfo.proName]}

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Chemical Structure| 65685-51-0
Chemical Structure| 65685-51-0
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Product Details of [ 65685-51-0 ]

CAS No. :65685-51-0 MDL No. :MFCD13193078
Formula : C7H4BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZXDOSRLQEYIVJC-UHFFFAOYSA-N
M.W : 214.02 Pubchem ID :11229627
Synonyms :

Calculated chemistry of [ 65685-51-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.53
TPSA : 46.0 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) : -6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.93
Solubility : 0.254 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.821 mg/ml ; 0.00384 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.68
Solubility : 0.0446 mg/ml ; 0.000208 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 65685-51-0 ]

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 [ 65685-51-0 ]

* 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 [ 65685-51-0 ]
  • Downstream synthetic route of [ 65685-51-0 ]

[ 65685-51-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 61799-79-9 ]
  • [ 65685-51-0 ]
YieldReaction ConditionsOperation in experiment
95% With 1,1'-carbonyldiimidazole In tetrahydrofuran for 2 h; Reflux (12) A solution of ,Γ-earbonyidiimidazoie (2.0 eq) in THF (0,1 M) was added dropwise to a rcfluxing solution of 4-bromo~2~hydroxy~be:nzertecari ohydfoxar)iie acid (1.0 eq) in THF (0.15 M) and then stirred for 2h at reihrxing conditions. The THF was removed under vacuum and the residue was suspended ia water. HO (2 ) was added dropwise at rt. A precipitate formed and was collected by filtration, washed with water and dried overnight ia a vacuum ovea to afford 6-bromo- 1 ,2-benzoxazol- 3-0.1 (95percent yield).
89% With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.533333 h; Inert atmosphere General procedure: Salicylhydroxamic acid 1a (77 mg, 0.5 mmol, 1 equiv) was dissolved in anhydrous THF (7 mL) under an inert (N2) atmosphere. Triphenylphosphine (164 mg, 0.625 mmol, 1.25 equiv) was then added. After 2 min, DIAD (123 lL, 0.625 mmol, 1.25 equiv) was added dropwise. TLC (Hex/EtOAc, 1:3) after 30 min revealed the reaction was complete. The THF was removed in vacuo. The residue was partitioned between 0.1 M NaOH (50 mL)and CH2Cl2 (100 mL). The organic layer was separated, then the aqueous layerwas washed a further three times with CH2Cl2 (100 mL). The aqueous layer was acidified with 1 M HCl (10 mL), then extracted into CH2Cl2 (2 100 mL),washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to yield the 3-hydroxybenzisoxazole 2a.
Reference: [1] Patent: WO2016/115282, 2016, A1, . Location in patent: Page/Page column 76; 77
[2] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5301 - 5303
[3] Patent: WO2004/10995, 2004, A1, . Location in patent: Page/Page column 37
  • 2
  • [ 546-88-3 ]
  • [ 179232-29-2 ]
  • [ 65685-51-0 ]
YieldReaction ConditionsOperation in experiment
31%
Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide for 0.5 h;
Stage #2: at 20℃; for 240 h;
Step A: 6-bromobenzo[d]isoxazol-3-ol: N-hydroxyacetamide (0.99 g, 12.9 mmol) was dissolved in DMF (20 mL). To this was added KOt-Bu (1.44 g, 12.9 mmol) and the reaction was stirred for 30 minutes before addition of methyl 4-bromo-2-fluorobenzoate (2.0 g, 8.58 mmol). The reaction mixture was stirred at ambient temperature for 10 days, then diluted with ethyl acetate (50 mL) and 1N NaOH (50 mL). The aqueous layer was washed with ethyl acetate, then acidified with 2N HCl (30 mL). The desired product was collected by filtration (570 mg, 31percent).
Reference: [1] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 62
  • 3
  • [ 1666-28-0 ]
  • [ 65685-51-0 ]
Reference: [1] Patent: WO2016/115282, 2016, A1,
[2] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5301 - 5303
  • 4
  • [ 22717-56-2 ]
  • [ 65685-51-0 ]
Reference: [1] Patent: WO2016/115282, 2016, A1,
[2] Tetrahedron Letters, 2016, vol. 57, # 48, p. 5301 - 5303
  • 5
  • [ 61799-79-9 ]
  • [ 65685-51-0 ]
Reference: [1] Australian Journal of Chemistry, 1977, vol. 30, p. 1847 - 1850
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