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[ CAS No. 104253-44-3 ] {[proInfo.proName]}

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Chemical Structure| 104253-44-3
Chemical Structure| 104253-44-3
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Product Details of [ 104253-44-3 ]

CAS No. :104253-44-3 MDL No. :MFCD04117954
Formula : C8H7ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :BJZFMXJQJZUATE-UHFFFAOYSA-N
M.W : 186.59 Pubchem ID :13498830
Synonyms :

Calculated chemistry of [ 104253-44-3 ]

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 : 44.75
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) : -5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : 3.07
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 2.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.126 mg/ml ; 0.000678 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.036 mg/ml ; 0.000193 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.52
Solubility : 0.569 mg/ml ; 0.00305 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 104253-44-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104253-44-3 ]

* 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 [ 104253-44-3 ]
  • Downstream synthetic route of [ 104253-44-3 ]

[ 104253-44-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 67-56-1 ]
  • [ 56363-84-9 ]
  • [ 104253-44-3 ]
YieldReaction ConditionsOperation in experiment
100% for 12 h; Reflux SOCl2 (1.5 ml) was added to 2-chloro-4-hydroxy-benzoic acid (5 g, 0.03 mmol) in methanol (10 ml). The mixturewas slowly warmed from room temperature to reflux temperature and the reaction solution was refluxed for 12 hoursand concentrated under reduced pressure to give compound 132A (red solid, 5.4 g, the yield was 100percent).1H NMR (400MHz, DMSO-d6) δ: 10.71 (s, 1H), 7.84 - 7.71 (m, 1H), 6.91 (d, J=2.4 Hz, 1H), 6.82 (dd, J=2.4, 8.7 Hz, 1H),3.79 (s, 3H).
92% for 72 h; Heating / reflux A solution of 2-chloro-4-hydroxybenzoic acid (4.20 g) and concentrated sulfuric acid (2.5 mL) in methanol (50 mL) was heated under reflux for three days. The reaction mixture was neutralized with a saturated sodium hydrogen carbonate aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate and concentrated and dried under reduced pressure, and 4.18 g (92percent) of the title compound was obtained as a brown solid.1H NMR(400MHz,CDCl3):δ(ppm)=7.83(1H, d, J=8.6Hz), 6.94(1H, d, J=2.7Hz), 6.76(1H, dd, J=8.6 and 2.4Hz), 5.63(1H, s), 3.89(3H, s).
92.5% at 0 - 70℃; for 2 h; To a solution of 2-chloro-4-hydroxybenzoic acid (200.0 mg, 1.16 mmol) in methanol (5 mL) was added thionyl chloride (413.6 mg, 3.48 mmol) dropwise at 0 °C. The reaction mixture was stirred at 70 °C for 2 h and concentrated. The residue was diluted withwater (15 mL) and extracted with EtOAc (l5mL x 2). The organic layers were combined and washed with water (30 mL x 2) and brine (20 mL). The organic layers were separated, dried over Na2504 and concentrated to obtain methyl 2-chloro-4-hydroxy-benzoate (200 mg, 92.5percent yield) as a yellow solid which was used directly without further purification.
92.5% at 0 - 70℃; for 2 h; To a solution of 2-chloro-4-hydroxybenzoic acid (200.0 mg, 1.16 mmol) in methanol (5 mL) was added thionyl chloride (413.6 mg, 3.48 mmol) dropwise at 0 °C. The reaction mixture was stirred at 70°C for 2 h and concentrated. The residue was diluted withwater (15 mL) and extracted with EtOAc (15 mL x 2). The organic layers were combined and washed with water (30 mL x 2) and brine (20 mL). The organic layers were separated, dried over Na2504 and concentrated to obtain methyl 2-chloro-4-hydroxy-benzoate (200 mg, 92.5percent yield) as a yellow solid which was used directly without further purification.
81%
Stage #1: for 1.5 h; Reflux
Stage #2: Cooling
2-chloro-4-hydroxybenzoic acid (98.0 g, 46.4 mmol) was treated with concentrated H2SO4 (6.5 ml_, 122 mmol) in methanol (45 ml.) and stirred at reflux for 1.5 h. The reaction mixture was cooled in an ice bath. 1 N NaOH (122 ml.) was added dropwise with stirring and cooling and the resultant precipitate was filtered off, washed three times with water and air dried to give the title compound (7.05 g, 37.8 mmol, 81 percent) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.69 (s, 1 H), 7.77 (d, 1 H), 6.90 (d, 1 H), 6.81 (dd, 1 H), 3.79 (s, 3 H).

Reference: [1] Patent: EP3293177, 2018, A1, . Location in patent: Paragraph 0332; 0333
[2] Patent: EP1764360, 2007, A1, . Location in patent: Page/Page column 176-177
[3] Patent: WO2017/84629, 2017, A1, . Location in patent: Paragraph 00316
[4] Patent: WO2017/84630, 2017, A1, . Location in patent: Paragraph 00648
[5] Patent: WO2008/157330, 2008, A1, . Location in patent: Page/Page column 87
[6] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5755 - 5775
[7] ChemMedChem, 2014, vol. 9, # 1, p. 67 - 72
[8] Patent: WO2018/68295, 2018, A1, . Location in patent: Page/Page column 55; 56
  • 2
  • [ 2457-76-3 ]
  • [ 104253-44-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 26, p. 5755 - 5775
  • 3
  • [ 3336-16-1 ]
  • [ 104253-44-3 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 1, p. 67 - 72
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