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[ CAS No. 35450-36-3 ]

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3d Animation Molecule Structure of 35450-36-3
Chemical Structure| 35450-36-3
Chemical Structure| 35450-36-3
Structure of 35450-36-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35450-36-3 ]

CAS No. :35450-36-3 MDL No. :MFCD00051594
Formula : C9H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VRTQLDFCPNVQNT-UHFFFAOYSA-N
M.W :245.07 Pubchem ID :2776849
Synonyms :

Calculated chemistry of [ 35450-36-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.91
TPSA : 35.53 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) : -5.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.46
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 2.39
Consensus Log Po/w : 2.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0509 mg/ml ; 0.000208 mol/l
Class : Soluble
Log S (Ali) : -3.89
Solubility : 0.0317 mg/ml ; 0.000129 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.085 mg/ml ; 0.000347 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 35450-36-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 35450-36-3 ]

* 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 [ 35450-36-3 ]
  • Downstream synthetic route of [ 35450-36-3 ]

[ 35450-36-3 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 35450-36-3 ]
  • [ 5043-54-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
[2] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
  • 2
  • [ 35450-36-3 ]
  • [ 42523-29-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1973, p. 910 - 935
  • 3
  • [ 35450-36-3 ]
  • [ 60080-98-0 ]
Reference: [1] Tetrahedron, 2001, vol. 57, # 36, p. 7765 - 7770
  • 4
  • [ 67-56-1 ]
  • [ 22921-68-2 ]
  • [ 35450-36-3 ]
YieldReaction ConditionsOperation in experiment
85% for 18 h; Heating / reflux To a stirred solution of 2-bromo-5-methoxybenzoic acid (Aldrich 384003; 5.0 g, 21.6 mmol) in methanol (80 mL) was added concentrated hydrochloric acid (2 mL) and the mixture was heated under reflux for 18 hours. The resulting solution was cooled, the solvent was removed in vacuo, water (100 mL) was added and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined extracts were washed with saturated aqueous sodium hydrogen carbonate, dried over MgSO4, filtered and evaporated to obtain methyl 2-bromo-5-methoxybenzoate as a light brown oil (4.50 g, 85percent); NMR Spectrum δH (300 MHz, CDCl3) 7.53 (1 H, d, J 8.8 Hz, 3-H), 7.32 (1 H, d, J 3.0 Hz, 6-H), 6.89 (1 H, dd, J 3.0, 8.8 Hz, 4-H), 3.94 (3 H, s, Ar OCH3) and 3.82 <n="66"/>(3 H, s, CO2CH3) (data in accordance with published values, see Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55, 11127- 11142); vmjcnfl (thin film) 2951, 1732 (C=O), 1592, 1472, 1433, 1289, 1250, 1227, 1099, 1017, 975, 823, 792 (data in accordance with published values, see Barhate, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. V. Tetrahedron 1999, 55, 11127-11142.); Rf (hexane - ethyl acetate 5:1) 0.58.
Reference: [1] Tetrahedron, 1998, vol. 54, # 37, p. 11209 - 11234
[2] Journal of Organic Chemistry, 2003, vol. 68, # 11, p. 4586 - 4589
[3] Patent: WO2012/102985, 2012, A1, . Location in patent: Page/Page column 111
[4] Patent: WO2008/75048, 2008, A2, . Location in patent: Page/Page column 64-65
[5] Tetrahedron, 1995, vol. 51, # 37, p. 10115 - 10124
[6] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 17, p. 4601 - 4611
[7] Tetrahedron, 2016, vol. 72, # 24, p. 3454 - 3467
  • 5
  • [ 1083407-17-3 ]
  • [ 35450-36-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7053 - 7056
  • 6
  • [ 22921-68-2 ]
  • [ 35450-36-3 ]
Reference: [1] Yakugaku Zasshi, 1956, vol. 76, p. 1122,1125[2] Chem.Abstr., 1957, p. 3505
[3] Patent: US6514964, 2003, B1,
  • 7
  • [ 5368-81-0 ]
  • [ 35450-36-3 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 35, p. 6349 - 6350
[2] Tetrahedron, 1999, vol. 55, # 36, p. 11127 - 11142
  • 8
  • [ 22921-68-2 ]
  • [ 74-88-4 ]
  • [ 35450-36-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 222 - 227
  • 9
  • [ 75-91-2 ]
  • [ 22921-68-2 ]
  • [ 35450-36-3 ]
Reference: [1] Dalton Transactions, 2015, vol. 44, # 14, p. 6546 - 6559
[2] Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9898 - 9905
  • 10
  • [ 67-56-1 ]
  • [ 56658-04-9 ]
  • [ 35450-36-3 ]
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 15, p. 5264 - 5271
  • 11
  • [ 35450-36-3 ]
  • [ 150192-39-5 ]
YieldReaction ConditionsOperation in experiment
94.9% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h; To a stirred suspension of lithium aluminum hydride (1.2 g, 30.6 mmol) in dry tetrahydrofuran (40 ml) was added a solution of methyl 2-bromo-5-methoxybenzoate (5.0 g, 20.4 mmol) in dry tetrahydrofuran (80 ml) dropwise under nitrogen at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added sodium sulfate decahydrate and potassium fluoride. The resulting mixture was stirred at room temperature for 1 hr, and filtered through a celite pad. The filtrate was concentrated to give crude products as a white crystal. This was purified by silica-gel column chromatography eluted with a gradient of hexane and ethyl acetate (10:1, 8:1, 6:1) to give the title compound as a white crystal (4.2 g, 94.9percent). [0097] 1H-NMR(CDCl3): 7.42 (d, J=8.8 Hz, 1H), 7.07 (d, J=2.9 Hz, 1H), 6.72 (dd, J=8.8, 2.9 Hz, 1H), 4.71 (d, J=6.2 Hz, 2H), 3.81 (s, 3H), 1.98 (t, J=6.2 Hz, 1H)
Reference: [1] Tetrahedron, 1998, vol. 54, # 37, p. 11209 - 11234
[2] Patent: US2003/208079, 2003, A1, . Location in patent: Page/Page column 8
[3] Patent: US6514964, 2003, B1,
  • 12
  • [ 35450-36-3 ]
  • [ 22246-66-8 ]
Reference: [1] Patent: WO2007/84451, 2007, A1,
  • 13
  • [ 35450-36-3 ]
  • [ 788081-99-2 ]
Reference: [1] Patent: WO2007/84451, 2007, A1,
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