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[ CAS No. 882-09-7 ] {[proInfo.proName]}

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Chemical Structure| 882-09-7
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Product Details of [ 882-09-7 ]

CAS No. :882-09-7 MDL No. :MFCD00004192
Formula : C10H11ClO3 Boiling Point : -
Linear Structure Formula :ClC6H4OC(CH3)2COOH InChI Key :TXCGAZHTZHNUAI-UHFFFAOYSA-N
M.W : 214.65 Pubchem ID :2797
Synonyms :
Chlorofibrinic acid;NSC 1149;CCRIS9254 Chlorfibrinic acid;CCRIS 9254;BRN 1874067
Chemical Name :2-(4-Chlorophenoxy)-2-methylpropanoic acid

Calculated chemistry of [ 882-09-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.17
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) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.57
Log Po/w (WLOGP) : 2.58
Log Po/w (MLOGP) : 2.23
Log Po/w (SILICOS-IT) : 2.11
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.265 mg/ml ; 0.00123 mol/l
Class : Soluble
Log S (Ali) : -3.2
Solubility : 0.137 mg/ml ; 0.000638 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.236 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 882-09-7 ]

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

Application In Synthesis of [ 882-09-7 ]

* 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 [ 882-09-7 ]
  • Downstream synthetic route of [ 882-09-7 ]

[ 882-09-7 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 54504-70-0 ]
  • [ 882-09-7 ]
  • [ 519-37-9 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 116, p. 2045 - 2053
  • 2
  • [ 637-07-0 ]
  • [ 882-09-7 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 16 h;
Stage #2: With hydrogenchloride In tetrahydrofuran
Step 2:; Synthesis of 2-(4-chloro-phenoxy)-2-methyl-propionic acid; To a solution of 2-(4-chloro-phenoxy)-2-methyl-propionic acid ethyl ester (2.0 g, 8.24 mmol) in tetrahydrofuran (16 rnL) at room temperature is added water (4 mL) followed by lithium hydroxide monohydrate (0.69 g, 16.4 mmol). The reaction is stirred for 16 h at room temperature. After this time, the mixture is diluted with water and washed with DCM. The aqueous phase is separated, acidified to pH ~2 with IM aqueous HCl solution and then extracted with DCM (x2). The combined organic extracts are washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give the title compound as a white solid (1.45 g, 82percent). IH NMR (400 MHz, CHLOROFORM-d): δ ppm 1.62 (6H, s), 6.89 (2H, d, J=9.0 Hz), 7.24 (2H, d, J=9.0 Hz).
20%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 20℃; for 12 h;
Stage #2: With hydrogenchloride; water In ethyl acetate at 0℃;
2-(4-Chloro-phenoxy)-2-methyl-propionic acid (Al-II):To a solution of 2-(4-Chloro-phenoxy)-2-methyl-propionic acid ethyl ester ( 6 g, 24.79 mmol) in THF (20 ml) was added a solution of LiOH ( 3 g, 74.38 mmol) in H2O ( 4 mil). The resulting solution was stirred at room temperature for 12 hours. After evaporation of the solvent, the residue was diluted with ethyl acetate (100 ml); cool to OoC, acidified with IN HCl (PH- 3-4). The organic phase were washed with, brine (20 ml) and dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:1 hexanes/ EtOAc) to give 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (1.1 g, 20 percent). 1H NMR (400 MHz, CDCl3): δ 1.60 (s, 6H), 6.85 (d, J=8.7 Hz, 2H), 7.22 (d, J=8.7 Hz, 2H). MS (EI) mlz: 215.5 (M + 1).
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 681 - 694
[2] Patent: WO2009/105509, 2009, A1, . Location in patent: Page/Page column 36-37
[3] Journal of Pharmaceutical Sciences, 1980, vol. 69, # 1, p. 92 - 93
[4] Patent: WO2008/104994, 2008, A2, . Location in patent: Page/Page column 32-33
[5] Patent: US2009/197959, 2009, A1, . Location in patent: Page/Page column 18
  • 3
  • [ 60-35-5 ]
  • [ 36637-30-6 ]
  • [ 882-09-7 ]
YieldReaction ConditionsOperation in experiment
85% With sodium sulfite In hexane at 65℃; for 2.16667 h; Reflux In a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 70 mass percent p-chlorfenoxamine solution (2)0.62mol, hexane 300ml, sodium sulfite solution 500ml, mass fraction 60percent acetamide solution (3) 0.73mol, control the stirring speed 160rpm,The temperature of the solution was raised to 65 ° C, and the mass fraction of the solution (4) 0.79 mol of 45percent 1-bromo-methylenediamine was added dropwise. After the addition,Adding 30percent oxalic acid to adjust the solution to pH 5, reducing the temperature of the solution to 7 DEG C, precipitating the solid, filtering, washing with ammonium bromide solution,The results showed that the scavenging activity of the active alumina was 97percent, the mass fraction was 86percent, the ethylenediamine was washed, the active alumina was dehydrated, and the mass fraction was 97percent nitromethane.Crystal, the crystal of chlorophenoxyisobutyric acid 113.31g, yield 85percent.
Reference: [1] Patent: CN105503564, 2016, A, . Location in patent: Paragraph 0005; 0013; 0014
  • 4
  • [ 2052-01-9 ]
  • [ 106-48-9 ]
  • [ 882-09-7 ]
Reference: [1] Synthesis, 2004, # 12, p. 1959 - 1962
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 11, p. 1712 - 1719
[3] Journal of the Chinese Chemical Society, 2007, vol. 54, # 3, p. 575 - 578
[4] Journal of the American Chemical Society, 2013, vol. 135, # 20, p. 7567 - 7571
  • 5
  • [ 31637-97-5 ]
  • [ 59-67-6 ]
  • [ 882-09-7 ]
  • [ 107-21-1 ]
Reference: [1] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2008, vol. 70, # 5, p. 1231 - 1237
  • 6
  • [ 106-48-9 ]
  • [ 57-15-8 ]
  • [ 882-09-7 ]
Reference: [1] Canadian Journal of Chemistry, 1989, vol. 67, p. 1472 - 1479
  • 7
  • [ 616-91-1 ]
  • [ 882-09-7 ]
Reference: [1] Chemical Research in Toxicology, 2001, vol. 14, # 8, p. 1033 - 1040
  • 8
  • [ 67-66-3 ]
  • [ 106-48-9 ]
  • [ 67-64-1 ]
  • [ 882-09-7 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 17, p. 3011 - 3013
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 168 - 170
[3] Medicinal Chemistry, 2012, vol. 8, # 2, p. 293 - 298
[4] European Journal of Organic Chemistry, 2017, vol. 2017, # 15, p. 2154 - 2163
  • 9
  • [ 106-48-9 ]
  • [ 882-09-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 681 - 694
  • 10
  • [ 600-00-0 ]
  • [ 1193-00-6 ]
  • [ 882-09-7 ]
Reference: [1] Annals of Applied Biology, 1955, vol. 43, p. 342,343, 344[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1959, vol. 150, p. 95,96, 100
[3] Bulletin de la Societe Chimique de France, 1956, p. 776,780, 781
  • 11
  • [ 106-48-9 ]
  • [ 67-64-1 ]
  • [ 882-09-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1947, vol. 77, p. 431,435
  • 12
  • [ 637-07-0 ]
  • [ 64-17-5 ]
  • [ 882-09-7 ]
Reference: [1] Journal of pharmaceutical sciences, 1982, vol. 71, # 1, p. 14 - 25
  • 13
  • [ 31637-97-5 ]
  • [ 3612-80-4 ]
  • [ 882-09-7 ]
Reference: [1] Journal of pharmaceutical sciences, 1982, vol. 71, # 1, p. 14 - 25
  • 14
  • [ 63394-05-8 ]
  • [ 882-09-7 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 10 A, p. 1786 - 1790
  • 15
  • [ 31637-97-5 ]
  • [ 59-67-6 ]
  • [ 3612-80-4 ]
  • [ 882-09-7 ]
  • [ 31637-96-4 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 3, p. 295 - 299
  • 16
  • [ 54504-70-0 ]
  • [ 882-09-7 ]
  • [ 519-37-9 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 116, p. 2045 - 2053
  • 17
  • [ 56-23-5 ]
  • [ 67-66-3 ]
  • [ 106-48-9 ]
  • [ 67-64-1 ]
  • [ 882-09-7 ]
Reference: [1] Gazzetta Chimica Italiana, 1947, vol. 77, p. 431,435
  • 18
  • [ 882-09-7 ]
  • [ 637-07-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1956, p. 776,780, 781
[2] Synthetic Communications, 2003, vol. 33, # 16, p. 2885 - 2890
[3] Bulletin de la Societe Chimique de France, 1956, p. 776,780, 781
  • 19
  • [ 64-17-5 ]
  • [ 882-09-7 ]
  • [ 637-07-0 ]
Reference: [1] Journal of Pharmaceutical Sciences, 1993, vol. 82, # 2, p. 214 - 219
  • 20
  • [ 882-09-7 ]
  • [ 943-45-3 ]
Reference: [1] Patent: US5192785, 1993, A,
[2] Patent: US5194446, 1993, A,
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