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[ CAS No. 133921-27-4 ] {[proInfo.proName]}

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Chemical Structure| 133921-27-4
Chemical Structure| 133921-27-4
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Product Details of [ 133921-27-4 ]

CAS No. :133921-27-4 MDL No. :MFCD09029708
Formula : C7H7IO Boiling Point : -
Linear Structure Formula :- InChI Key :IYKHMSCHNOEGSE-UHFFFAOYSA-N
M.W : 234.03 Pubchem ID :10421515
Synonyms :

Calculated chemistry of [ 133921-27-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.15
TPSA : 20.23 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.31
Log Po/w (MLOGP) : 2.72
Log Po/w (SILICOS-IT) : 2.79
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.37
Solubility : 0.0994 mg/ml ; 0.000425 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.6 mg/ml ; 0.00256 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.17
Solubility : 0.159 mg/ml ; 0.000681 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 133921-27-4 ]

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

Application In Synthesis of [ 133921-27-4 ]

* 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 [ 133921-27-4 ]
  • Downstream synthetic route of [ 133921-27-4 ]

[ 133921-27-4 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
61% at 80℃; for 5 h; 4.2 g (18 mmol) of 4-iodo-3-methylphenol are dissolved in 90 ml of anhydrous methanol and then placed in a steel reactor. 5 ml (35 mmol) of triethylamine and 400 mg (1.8 mmol) of palladium diacetate are added, the reaction medium is subjected to a carbon monoxide pressure of 3 bar and heated at 80° C. for 5 hours. The medium is then brought to ambient pressure and temperature and then dissolved in dichloromethane and filtered on celite. After evaporation, the residue is purified by chromatography on a silica column. An orange-coloured powder is obtained (m=1.8 g, Y=61 g).
Reference: [1] Patent: US6689922, 2004, B1, . Location in patent: Page column 85-86
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YieldReaction ConditionsOperation in experiment
47%
Stage #1: With hydrogenchloride; sodium nitrite In tetrahydrofuran; water at 0℃;
Stage #2: With potassium iodide In tetrahydrofuran; water at 0℃; for 0.25 h;
Example 25: Synthesis of(E)-4-((2-(4-((Z)-l-(4-hydroxyphenyl)-2-phenylbut-l-en-l-yl)-3- methylphenoxy)ethyl)amino)-N,N-dimethylbut-2-enamide Step-1: Synthesis of 4-iodo-3-methylphenol 3 M HCI/ J To a solution of 4-amino-3-methylphenol (10 g, 81 mmol) in THF (45 mL) was added 3M HC1 (35 mL) at 0 °C over a period of 10 min followed by NaN02 (6.1 g, 89 mmol). To the above reaction mixture, potassium iodide (53.89 g, 166 mmol) in water (140 mL) was added dropwise and stirred at 0 °C for 15 min. After completion of reaction, reaction mixture was extracted with EtOAc. Organic layer was washed water followed by brine, concentared under reduced pressure to obtain the crude compound. Crude material was purified by column chromatography over 230-400 mesh silica gel using 10percent EtOAc in n-hexane to give the title compound (9 g, 47percent).
15%
Stage #1: With sulfuric acid; sodium nitrite In water at 0℃; for 0.333333 h;
Stage #2: With copper(l) iodide; sulfuric acid; potassium iodide In water at 0℃; for 3 h; Heating / reflux
15 g (122 mol) of 4-hydroxy-2-methylaniline are dissolved in 180 ml of 20percent sulphuric acid and then the reaction medium is cooled to 0° C. A solution of sodium nitrite (11.3 g, 163 mmol) in 60 ml of water is then added dropwise and then the medium is stirred for 20 minutes. This solution is then slowly added to a solution at 0° C. of CuI (32.5 g, 170 mmol) and KI (31.9 g, 193 mmol) in 180 ml of 20percent sulphuric acid. The reaction medium is heated under reflux for 3 hours, poured into 1 l of water and extracted with ethyl ether. The organic phases are washed with a saturated sodium thiosulphate solution, of water, dried over magnesium sulphate and concentrated under reduced pressure. After purification on a silica column (ethyl acetate 30-heptane 70), a brown oil is obtained (m 4.2 g; Y=15percent).
Reference: [1] Patent: WO2016/196342, 2016, A1, . Location in patent: Page/Page column 129
[2] Patent: US6689922, 2004, B1, . Location in patent: Page column 85
[3] Journal of the Chemical Society, 1951, p. 1184,1186
[4] Patent: US6562823, 2003, B1,
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YieldReaction ConditionsOperation in experiment
75% With tetra-(n-butyl)ammonium iodide; isoquinolinium chlorochromate In water at 25 - 30℃; for 4 h; General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.
70% With potassium hydrogensulfate; potassium iodide; isoquinolinium chlorochromate In water at 50 - 60℃; General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines,or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4–5 h at 50–60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5percent sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure product.General
Reference: [1] Chinese Chemical Letters, 2012, vol. 23, # 3, p. 261 - 264
[2] Synthetic Communications, 2008, vol. 38, # 17, p. 2881 - 2888
[3] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 3, p. 258 - 261
[4] Catalysis Communications, 2017, vol. 93, p. 1 - 4
[5] Asian Journal of Chemistry, 2018, vol. 30, # 8, p. 1892 - 1896
[6] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2016, vol. 46, # 6, p. 832 - 837
[7] Tetrahedron Letters, 2010, vol. 51, # 16, p. 2170 - 2173
[8] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[9] Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 586 - 592
[10] Journal of Organic Chemistry, 1994, vol. 59, # 15, p. 4285 - 4296
[11] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1981, vol. 20, # 2, p. 133 - 135
[12] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6124 - 6128
[13] International Journal of Chemical Kinetics, 2013, vol. 45, # 11, p. 693 - 702
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Reference: [1] Synthetic Communications, 2008, vol. 38, # 22, p. 3894 - 3902
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Reference: [1] Monatshefte fur Chemie, 2012, vol. 143, # 7, p. 1039 - 1044
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  • [ 60577-32-4 ]
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Reference: [1] Russian Journal of Applied Chemistry, 2012, vol. 85, # 9, p. 1355 - 1365[2] Russ. J. Appl. Chem, 2012, vol. 85, # 9, p. 1355 - 1365,11
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