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[ CAS No. 54232-43-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 54232-43-8
Chemical Structure| 54232-43-8
Chemical Structure| 54232-43-8
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Product Details of [ 54232-43-8 ]

CAS No. :54232-43-8 MDL No. :MFCD06655957
Formula : C7H6BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WOXIJGVDMQJTAC-UHFFFAOYSA-N
M.W : 232.03 Pubchem ID :7471965
Synonyms :

Calculated chemistry of [ 54232-43-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.39
TPSA : 59.42 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : -0.6
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.59
Solubility : 0.591 mg/ml ; 0.00255 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.62 mg/ml ; 0.00267 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.39
Solubility : 0.954 mg/ml ; 0.00411 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 54232-43-8 ]

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 [ 54232-43-8 ]

* 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 [ 54232-43-8 ]
  • Downstream synthetic route of [ 54232-43-8 ]

[ 54232-43-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 24207-22-5 ]
  • [ 54232-43-8 ]
YieldReaction ConditionsOperation in experiment
75% With potassium permanganate In water at 80℃; [0125] 2-Bromo-3-methoxy-6-methylpyridine (XXXXV) 760 mg (3.76 mmol) was dissolved in 15 ml of water, and to the resulting solution was added potassium permanganate (KMnO4) (1.49 g, 9.40mmol) and the mixture was heated at 80 °C for 3 hrs.
After TLC was conducted, pH was adjusted to 4 with 10percent hydrochloric acid (HCl) and filtration was conducted with celite.
The filtrate was extracted with 50 ml of ethylacetate (EA).
The organic layer was treated with magnesium sulfate (MgSO4) and filtered, and the solution was concentrated to give the title compound as a white solid (665 mg, 2.87 mmol, 75 percent) without purification.
1H NMR (400 MHz, DMSO-d6) δ 13.22 (s, OH), 8.05 (d, J = 8.0 Hz, 1H), 7.60 (d, J = 8.0 Hz, 1H), 4.02 (s, 3H).
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: EP3255042, 2017, A2, . Location in patent: Paragraph 0122; 0125
[3] Tetrahedron Letters, 1995, vol. 36, # 30, p. 5319 - 5322
[4] Patent: WO2014/78690, 2014, A1, . Location in patent: Paragraph 00201
[5] Patent: WO2016/29214, 2016, A1, . Location in patent: Page/Page column 148
  • 2
  • [ 672957-93-6 ]
  • [ 54232-43-8 ]
YieldReaction ConditionsOperation in experiment
61% at 80℃; for 3 h; 5-Methoxy-1-oxy-pyridine-2-carboxylic acid (1.2 g, 7 mmol) was added to phosphorus oxybromide (CAN 7789-59-5, 10 g) at 80° C. and stirred for 3 h. The mixture was poured into water (100 mL), extracted with ethyl acetate (3.x.50 mL), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, 60 g, eluting with 10percent methanol in methylene chloride) to give the title compound (1 g, 61percent); MS (EI): m/e=232.0 [M+H]+.
61% at 80℃; for 3 h; 5-Methoxy-l-oxy-pyridine-2-carboxylic acid (1.2 g, 7 mmol) was added to phosphorus oxybromide (CAN 7789-59-5, 10 g) at 80°C and stirred for 3 h. The mixture was poured into water (100 mL), extracted with ethyl acetate (3 x 50 mL), dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (silica gel, 60 g, eluting with 10percent methanol in methylene chloride) to give the title compound (1 g, 61percent); MS (EI): m/e = 232.0 [M+H]+.
Reference: [1] Patent: US2012/316147, 2012, A1, . Location in patent: Page/Page column 65
[2] Patent: WO2012/168350, 2012, A1, . Location in patent: Page/Page column 138
  • 3
  • [ 1121-78-4 ]
  • [ 54232-43-8 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: WO2014/78690, 2014, A1,
[3] Patent: WO2016/29214, 2016, A1,
[4] Patent: EP3255042, 2017, A2,
  • 4
  • [ 23003-35-2 ]
  • [ 54232-43-8 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[2] Patent: WO2014/78690, 2014, A1,
[3] Patent: WO2016/29214, 2016, A1,
[4] Patent: EP3255042, 2017, A2,
  • 5
  • [ 29082-92-6 ]
  • [ 54232-43-8 ]
Reference: [1] Patent: US2012/316147, 2012, A1,
[2] Patent: WO2012/168350, 2012, A1,
  • 6
  • [ 54232-43-8 ]
  • [ 79-22-1 ]
  • [ 170235-18-4 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 30, p. 5319 - 5322
[2] Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4623 - 4633
[3] Patent: WO2014/78690, 2014, A1, . Location in patent: Paragraph 00201
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