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[ CAS No. 588-22-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 588-22-7
Chemical Structure| 588-22-7
Chemical Structure| 588-22-7
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Product Details of [ 588-22-7 ]

CAS No. :588-22-7 MDL No. :MFCD00004303
Formula : C8H6Cl2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SNYRXHULAWEECU-UHFFFAOYSA-N
M.W : 221.04 Pubchem ID :11495
Synonyms :

Calculated chemistry of [ 588-22-7 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.53
TPSA : 46.53 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) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 2.81
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 2.21
Log Po/w (SILICOS-IT) : 2.38
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.12
Solubility : 0.166 mg/ml ; 0.000751 mol/l
Class : Soluble
Log S (Ali) : -3.44
Solubility : 0.0795 mg/ml ; 0.00036 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.16
Solubility : 0.154 mg/ml ; 0.000698 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 588-22-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 588-22-7 ]

* 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 [ 588-22-7 ]
  • Downstream synthetic route of [ 588-22-7 ]

[ 588-22-7 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 62855-72-5 ]
  • [ 588-22-7 ]
YieldReaction ConditionsOperation in experiment
97% With sodium hydroxide In methanol at 20℃; for 1 h; General procedure: To a stirred solution of 4j (2.5 g, 9.8 mmol) in MeOH (30 mL) was added 3N NaOH solution (13.1 mL, 39.3 mmol). After being stirred at room temperature for 1 h, the mixture was diluted with water (100 mL), acidified with 3N HCl, and extracted with dichloromethane (100 mL × 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title compound (2.12 g, 97percent yield) . 1H NMR (300MHz, DMSO-d6) δ 7.49(d, J = 8.8 Hz, 1H), 7.21 (s, 1H), 6.92 (d, J = 8.8 Hz, 1H),4.73 (s, 2H).
75% With lithium hydroxide monohydrate In tetrahydrofuran; water at 0 - 20℃; for 1 h; To a solution of ethyl 2-(3, 4-dichlorophenoxy) acetate (1 .5g 6.04mmol, 1 equiv) in THF (15 mL), water (5 mL) at 0 °C was added UOH.H20 (0.62 g, 15.1 mmol 2.5 equiv) and the reaction mixture was stirred at room temperature for 1 h. After consumption of the starting material (TLC, 5 percent Methanol in DCM), THF was removed under vacuum and the reaction mixture was diluted with water (10 mL) followed by extraction with Et20 (20 mL). The aqueous layer was acidified with 1 N HCI upto pH 3 and the precipitated product was filtered through a cintered funnel, washed with ice-cold water (10 mL) and dried under high vacuum to give 2-(3,4-dichlorophenoxy)acetic acid (1 g, 75percent yield) as white solid. LCMS (ES) m/z = 220.0 [M+H]+. NMR (400 MHz, DMSO- de) δ ppm 4.72 (s, 2 H), 6.92 - 6.95 (m, 1 H), 7.21 (d, J = 8.8 Hz, 1 H), 7.51 (d, J = 9.6 Hz, 1 H), 13.05 (bs, 1 H).
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 10, p. 2549 - 2552
[2] Patent: WO2017/212423, 2017, A1, . Location in patent: Page/Page column 97; 98
  • 2
  • [ 95-77-2 ]
  • [ 588-22-7 ]
Reference: [1] Bot. Gaz., 1951, vol. 112, p. 250,252, 253
[2] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 10, p. 2549 - 2552
[3] Patent: WO2017/212423, 2017, A1,
  • 3
  • [ 95-77-2 ]
  • [ 105-36-2 ]
  • [ 588-22-7 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 47, p. 8986 - 8993
  • 4
  • [ 32026-08-7 ]
  • [ 588-22-7 ]
Reference: [1] Bot. Gaz., 1951, vol. 112, p. 250,252, 253
  • 5
  • [ 39975-26-3 ]
  • [ 105-36-2 ]
  • [ 588-22-7 ]
Reference: [1] Contributions from Boyce Thompson Institute, 1945, vol. 14, p. 91,95, 96[2] Chem.Abstr., 1946, p. 1473
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