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[ CAS No. 56427-63-5 ] {[proInfo.proName]}

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Chemical Structure| 56427-63-5
Chemical Structure| 56427-63-5
Structure of 56427-63-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 56427-63-5 ]

CAS No. :56427-63-5 MDL No. :MFCD18642371
Formula : C11H13BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :NTRWNKUDEDMRBR-UHFFFAOYSA-N
M.W : 273.12 Pubchem ID :10333471
Synonyms :

Calculated chemistry of [ 56427-63-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 61.86
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.77
Log Po/w (XLOGP3) : 2.67
Log Po/w (WLOGP) : 2.61
Log Po/w (MLOGP) : 2.65
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.18 mg/ml ; 0.000658 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.234 mg/ml ; 0.000855 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.26
Solubility : 0.0149 mg/ml ; 0.0000546 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.18

Safety of [ 56427-63-5 ]

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 [ 56427-63-5 ]

* 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 [ 56427-63-5 ]
  • Downstream synthetic route of [ 56427-63-5 ]

[ 56427-63-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 56427-62-4 ]
  • [ 56427-63-5 ]
YieldReaction ConditionsOperation in experiment
52% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 78℃; Step B: Synthesis of ethyl 2-(bromomethyl)-4-methoxybenzoate as an intermediate <n="71"/>; [0175] A mixture of ethyl 4-methoxy-2-methylbenzoate (2.24 g, 11.5 mmol) in carbon tetrachloride (20 mL) was heated to 78 0C in an oil bath then a mixture of N- bromosuccinimide (2.26 g, 12.6 mmol) and benzoyl peroxide (0.28 g, 1.15 mmol) was added portionwise over 4 h. The mixture was stirred overnight at 78 °C. After this time, the reaction mixture was cooled to room temperature and the solids removed by filtration. The filtrate was concentrated under reduced pressure and purification by flash chromatography (silica, 1 :50 ethyl acetate/hexanes) afforded ethyl 2-(bromomethyl)-4-methoxybenzoate (1.60 g, 52percent) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.99 (d, J= 8.7 Hz, IH), 6.96 (s, IH), 6.86 (dd, J= 8.7, 2.6, IH), 4.96 (s, 2H), 4.37 (q, J= 7.1, 2H), 3.86 (s, 3H), 1.41 (t, J= 7.1 Hz, 3H); ESI MS m/z 273 [M+ H]+.
48% With N-Bromosuccinimide In tetrachloromethane for 6 h; Heating / reflux Ethyl 2-nnethyl-4-methoxybenzoate (583 mg, 3 mmol) andN-bromosuccinimide (1335 mg, 7.5 mmol) were added to carbon tetrachloride (8 mL), and the resultant was refluxed for six hours. After the reaction was completed, N-bromosuccinimide was filtered out and carbon tetrachloride was distilled under a reduced pressure. The resultant was purified by a column <n="28"/>chromatography on silica gel (hexane/ethyl acetate=40:1 ) to obtain 340 mg of the desired compound(yield 48percent).1H NMR (400 MHz, CDCI3) δ 7.99 (d, J=2.6 Hz, 1 H), 6.96 (d, J=2.6 Hz, 1 H), 6.85 (dd, J=8.8, 2.6 Hz, 1 H), 4.96 (s, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.86 (s, 3H), 1.40 (t, J=7.1 Hz, 3H).13C NMR (100 MHz, CDCI3) δ 166.15, 162.46, 141.56, 133.63, 121 .33, 117.03, 113.56, 60.93, 55.50, 31.91 , 14.29.
Reference: [1] Patent: WO2009/42907, 2009, A1, . Location in patent: Page/Page column 69-70
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5701 - 5704
[3] Patent: WO2009/54653, 2009, A2, . Location in patent: Page/Page column 25-26
[4] Journal of the American Chemical Society, 2005, vol. 127, # 39, p. 13656 - 13665
[5] Patent: US4585788, 1986, A,
[6] Asian Journal of Chemistry, 2013, vol. 25, # 10, p. 5325 - 5327
[7] Patent: US4082850, 1978, A,
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