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[ CAS No. 56256-14-5 ] {[proInfo.proName]}

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Chemical Structure| 56256-14-5
Chemical Structure| 56256-14-5
Structure of 56256-14-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 56256-14-5 ]

CAS No. :56256-14-5 MDL No. :MFCD08436017
Formula : C8H7BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :UEVXVBKBOFGKIN-UHFFFAOYSA-N
M.W : 231.04 Pubchem ID :16215867
Synonyms :

Calculated chemistry of [ 56256-14-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.59
TPSA : 46.53 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) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 2.48
Log Po/w (WLOGP) : 2.16
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 1.89
Consensus Log Po/w : 2.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.195 mg/ml ; 0.000846 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.183 mg/ml ; 0.000791 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.403 mg/ml ; 0.00175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.46

Safety of [ 56256-14-5 ]

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

Application In Synthesis of [ 56256-14-5 ]

* 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 [ 56256-14-5 ]
  • Downstream synthetic route of [ 56256-14-5 ]

[ 56256-14-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 67-56-1 ]
  • [ 56256-14-5 ]
  • [ 17100-63-9 ]
YieldReaction ConditionsOperation in experiment
90% for 24 h; Reflux General procedure: The benzoic acid (1-4 g)was dissolved in methanol (25-75 mL),before conc. H2SO4 (2-6 mL) was added dropwise while stirring.The reaction mixture was heated to reflux and stirred for 24 h. Thereaction mixture was quenched in a saturated aq NaHCO3 solution(100-200 mL) ensuring neutral to basic pH, and the aqueous phase was extracted with CH2Cl2 (4 x 50 mL). The combined organic phases were washed with saturated aq NaCl solution (25-50 mL),dried over anhydrous Na2SO4 and filtered. Concentration yielded the target compound in high yield and purity. Methyl 4-bromo-3-methoxybenzoate was prepared as described in Section 4.5, starting with 4-bromo-3-methoxybenzoic acid (845 mg, 3.67 mmol). The procedure yielded 808 mg(3.30 mmol, 90percent) of methyl 4-bromo-3-methoxybenzoate a white crystalline product;
69% at 0 - 20℃; for 16 h; Inert atmosphere Methyl 4-bromo-3-methoxybenzoate (0284) To a solution of 4-bromo-3-methoxybenzoic acid (10.0 g, 43.28 mmol) in methanol (400 mL) was added acetyl chloride (19 mL, 266.25 mmol) dropwise at 0° C. The resulting solution was then stirred for 16 h at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with ethyl aceate in hexane (0percent to 5percent gradient) to yield methyl 4-bromo-3-methoxybenzoate as white solid (7.3 g, 69percent). MS: m/z=245.0 [M+H]+.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 255 - 274
[2] Patent: US2016/376283, 2016, A1, . Location in patent: Paragraph 0283; 0284
  • 2
  • [ 56256-14-5 ]
  • [ 17100-64-0 ]
Reference: [1] Patent: US4707483, 1987, A,
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 819 - 823
  • 3
  • [ 17100-63-9 ]
  • [ 56256-14-5 ]
YieldReaction ConditionsOperation in experiment
66% With sodium hydroxide In methanol; water at 20℃; for 6 h; Aq. sodium hydroxide (2 M, 40 mL) was added to a solution of methyl 4-bromo-3-methoxy-benzoate (13, 6.52 g, 27.1 mmol) in methanol (200 mL) and the mixture was stirred for 6 h at room temp. Deionized water (100 mL) was added and methanol was distilled off in vacuo.The remaining aq. phase was washed with dichloromethane (3 x 100 mL) and acidified with hydrochloric acid (6 M). The precipitate was filtered off and was washed thoroughly with water yielding a colourless solid. Yield: 4.10 g (17.8 mmol, 66percent)(ref[5]: 89percent). M. p.: 220 °C.1H NMR (500 MHz, DMSO-d6): δ = 13.21 (br. s, 1H,CO2H), 7.71 (d, 1H,3J = 8.2 Hz, Ar-H-5), 7.54 (d, 1H,4J = 1.8 Hz, Ar-H-2), 7.46 (dd,1H,3J = 8.2 Hz,4J = 1.8 Hz, Ar-H-6), 3.91 (s, 3H, OCH3) ppm.13C NMR (125 MHz,DMSO-d6): δ = 167.1 (s, CO2H), 155.9 (s, Ar-C-3), 133.6 (d, Ar-C-5), 132.1 (s, Ar-C-1), 123.2 (d, Ar-C-6), 116.5 (s, Ar-C-4), 113.0 (d, Ar-C-2), 56.8 (q, OCH3) ppm. MS(EI, 70 eV): m/z = 230/232 (100/98) [M]+·.
56% With hydrogenchloride; lithium hydroxide In tetrahydrofuran; methanol To a solution of 4-bromo-3-methoxy-benzoic acid methyl ester (6.875 mmol, 1.676 mL) in a mixture 1:1 of THF/MeOH (15 ML), lithium hydroxide (7.553 mmol, 0.180 g) was added, and the reaction was stirred at RT overnight before distillation of volatiles.
The residue was diluted with water, acidified with a solution of HCl (1N), and stirred for 1 hour.
The formed precipitate was filtered off, and washed with water and petroleum ether to give 4-bromo-3-methoxy-benzoic acid. Yield: 56percent.
10.1 g With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1 h; To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification. 1H-NMR (300MHz, DMSO-d6): δ [ppm] = 3.87 (s, 3H), 7.42 (dd, 1 H), 7.50 (d, 1 H), 7.68 (d, 1 H), 13.21 (br. s., 1 H).
10.1 g With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 1 h; To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed in vacuum. Water was added and I N hydrochloric acid was added with ice bath cooling until pH 4 was reached. The precipitated solid was collected by filtration, washed with waterand dried in vacuum to give 10.1 g of the title compound, that was used without further purification.1H-NMR (300MHz, DMSO-d6): a [ppm] = 3.87 (5, 3H), 7.42 (dd, 1H), 7.50 (d, 1H),7.68 (d, 1H), 13.21 (br. s., 1H).
10.1 g With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 1 h; To a stirred solution of methyl 4-bromo-3-methoxybenzoate (11.2 g) in THF (130 mL), methanol (45 mL) and water (45 mL) was added a 1 M solution of lithium hydroxide in water (140 mL).
The mixture was stirred at room temperature for 1 h.
The solvent was removed in vacuum.
Water was added and 1 N hydrochloric acid was added with ice bath cooling until pH 4 was reached.
The precipitated solid was collected by filtration, washed with water and dried in vacuum to give 10.1 g of the title compound, that was used without further purification.
1H-NMR (300 MHz, DMSO-d6): δ [ppm]=3.87 (s, 3H), 7.42 (dd, 1H), 7.50 (d, 1H), 7.68 (d, 1H), 13.21 (br. s., 1H).

Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Patent: US2003/45557, 2003, A1,
[3] Patent: WO2011/64328, 2011, A1, . Location in patent: Page/Page column 79-80
[4] Patent: WO2012/143329, 2012, A1, . Location in patent: Page/Page column 89
[5] Patent: WO2013/87579, 2013, A1, . Location in patent: Page/Page column 96; 97
[6] Patent: WO2014/9219, 2014, A1, . Location in patent: Page/Page column 71
[7] Patent: WO2014/195276, 2014, A1, . Location in patent: Page/Page column 99
[8] Patent: WO2014/198594, 2014, A1, . Location in patent: Page/Page column 94; 95
[9] Patent: US2015/148542, 2015, A1, . Location in patent: Paragraph 0341-0343
  • 4
  • [ 2486-69-3 ]
  • [ 56256-14-5 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 26, p. 5963 - 5966
[2] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1518 - 1523
  • 5
  • [ 586-38-9 ]
  • [ 56256-14-5 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 12, p. 2445 - 2448
[2] Journal of Organic Chemistry, 2007, vol. 72, # 9, p. 3419 - 3429
  • 6
  • [ 106291-80-9 ]
  • [ 56256-14-5 ]
Reference: [1] Patent: WO2011/64328, 2011, A1,
[2] Patent: WO2012/143329, 2012, A1,
[3] Patent: WO2013/87579, 2013, A1,
[4] Patent: WO2014/9219, 2014, A1,
[5] Patent: WO2014/198594, 2014, A1,
[6] Patent: US2015/148542, 2015, A1,
  • 7
  • [ 99-06-9 ]
  • [ 56256-14-5 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
  • 8
  • [ 14348-38-0 ]
  • [ 56256-14-5 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
  • 9
  • [ 775-62-2 ]
  • [ 56256-14-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2202 - 2204
  • 10
  • [ 50870-44-5 ]
  • [ 56256-14-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973, p. 2202 - 2204
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