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Chemical Structure| 533-58-4 Chemical Structure| 533-58-4

Structure of 533-58-4

Chemical Structure| 533-58-4

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Product Details of [ 533-58-4 ]

CAS No. :533-58-4
Formula : C6H5IO
M.W : 220.01
SMILES Code : OC1=C(I)C=CC=C1
MDL No. :MFCD00013963
InChI Key :KQDJTBPASNJQFQ-UHFFFAOYSA-N
Pubchem ID :10784

Safety of [ 533-58-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 533-58-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 41.18
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.73
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.65
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.0
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.41
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.39
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.23

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.43
Solubility 0.082 mg/ml ; 0.000373 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.73
Solubility 0.414 mg/ml ; 0.00188 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.78
Solubility 0.366 mg/ml ; 0.00166 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.76 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.85

Application In Synthesis of [ 533-58-4 ]

* 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.

  • Downstream synthetic route of [ 533-58-4 ]

[ 533-58-4 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 533-58-4 ]
  • [ 28177-52-8 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride; diisopropylamine; In toluene; at 70.0℃; Synthesis of 2-( ( 2 '-C hloro-6 '-( pyridin-4-yl)biphenyl-4-yloxy)methyl)alpha uinoline (Example 382)2-Chloro-6-iodophenol Error. Objects cannot be created from editing field codes. <n="81"/>To a solution of 2-iodophenol (5.0 g) in toluene (200 niL) was added diisopropylamine (32 muL) and sulfuryl chloride (3.07 g) dropwise at 7O0C. After the addition, the mixture was stirred for another hour at 7O0C, before it was quenched with 1 N HCl solution. The organic layer was separated, the aqueous layer was extracted with dichloromethane (3 x 50 mL), and dried over Na2SO4. The product was purified by silica gel flash chromatography eluting with 20% ethyl acetate in heptane to give 2-chloro-6- iodophenol(4.84 g) as an off-white solid. 1H NMR (300 MHz, CDC13/TMS) delta 7.60 (dd, J = 8.1, 1.2 Hz, IH), 7.30 (dd, J = 8.1, 1.5 Hz, IH), 6.62 (dd, J= 8.1, 7.8 Hz, IH), 5.96 (br, IH); 13C NMR (75 MHz, CDCI3/TMS) delta 151.01, 137.94, 129.85, 123.03, 119.44, 83.81.
  • 2
  • [ 533-58-4 ]
  • [ 1483-73-4 ]
  • [ 34883-46-0 ]
  • 3
  • [ 533-58-4 ]
  • [ 19231-06-2 ]
  • [ 836-07-7 ]
  • 4
  • [ 533-58-4 ]
  • [ 214360-60-8 ]
  • [ 108779-65-3 ]
  • 5
  • [ 110-86-1 ]
  • [ 533-58-4 ]
  • [ 33421-36-2 ]
  • [ 54168-07-9 ]
  • [ 86610-20-0 ]
  • 7
  • [ 50-00-0 ]
  • [ 533-58-4 ]
  • [ 38170-02-4 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; magnesium chloride; In acetonitrile; at 10 - 72℃; for 2h; 4-(nitrooxy)butyl (2R)-7-benzyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3- carboxylate; Step 1; Preparation of 2-hydroxy-4-iodobenzaldehyde; [0168] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 0C, followed by paraformaldehyde (28.6 g, 954 mmole) and TEA (76 mL, 545 mmole) producing a 15 C exotherm. The solution was heated to 72 0C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 mL). The combined organic phases were washed with aqueous NaHCO3 solution (2 X 150 mL), aqueous IN HCl solution (2 X 150 mL), and brine (2 X 150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% Ethyl acetate/ Hexane). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79%) as a yellow solid. This salicylaldehyde was of suitable purity to use without further purification.
79% With triethylamine; magnesium chloride; In acetonitrile; at 10 - 72℃; for 2h; [0232] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 C, followed by PARAFORMALDEHYDE (28.6 g, 954 mmole) and TEA (76 mL, 545 mmole) producing a 15 C exotherm. The solution was heated to 72 C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 mL). The combined organic phases were washed with aqueous NAHC03 solution (2 X 150 mL), aqueous 1N HCL solution (2 X 150 mL), and brine (2 X 150 mL), dried OVER NA2S04, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% Ethyl ACETATE/HEXANE). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79%) as a yellow solid. This salicylaldehyde was of suitable purity to use without FURTHER PURIFICATION. HNMR (DMSO-D6/400 MHz) 10.95 (s, 1H), 10.19 (s, 1H), 7.33 (m, 3H), 4.31 (m, 1H).
79% With triethylamine; magnesium chloride; In acetonitrile; at 10 - 72℃; for 2h; EXAMPLE 14; (2R)-6-chIoro-5-(3,3-dimethylbutyl)-2-(trifluoromethyl)-l,7b- dihydrocyclopropa[c]chromene-la(2H)-carboxylic acid; Step 1. Preparation of 2-hydroxy-4-iodobenzaldehyde.; [0185] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 0C, followed by paraformaldehyde (28.6 g, 954 mmole) and TEA (76 niL, 545 mmole) producing a 15 C exotherm. The solution was heated to 72 0C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 niL). The combined organic phases were washed with aqueous NaHCO3 solution (2 X 150 mL), aqueous IN HCl solution (2 X 150 mL), and brine (2 X 150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5% Ethyl acetate/ Hexane). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79%) as a yellow solid. This salicylaldehyde was of suitable purity to use without further purification. 1HNMR (DMSO-J6/400 MHz) 10.95 (s, IH), 10.19 (s, IH), 7.33 (m, 3H), 4.31 (m, IH).
  • 8
  • [ 533-58-4 ]
  • [ 197007-87-7 ]
  • [ 1037830-79-7 ]
  • 9
  • [ 533-58-4 ]
  • pyridin-2-ylzinc(II) bromide [ No CAS ]
  • [ 33421-36-2 ]
  • 10
  • [ 591-87-7 ]
  • [ 533-58-4 ]
  • [ 4265-25-2 ]
  • 12
  • [ 533-58-4 ]
  • [ 2914-69-4 ]
  • [ 1393670-93-3 ]
  • 13
  • [ 533-58-4 ]
  • [ 1459793-02-2 ]
  • 14
  • [ 533-58-4 ]
  • [ 26638-43-7 ]
  • [ 136883-85-7 ]
YieldReaction ConditionsOperation in experiment
75% With pyridine; dmap; at 20℃; for 72h; General procedure: Typically to a stirred solution of the arylsulfonyl chloride (2.7 mmol) and 4-DMAP (28mg, 0.23 mmol) in pyridine (20 mL) at room temperature was added 2-iodophenol (0.50g, 2.3 mmol), and the reaction mixture stirred for 3 days at room temperature. The reaction mixture was concentrated, dissolved in toluene (ca. 10 mL) and the resulting solution evaporated in vacuo to azeotropically remove the pyridine. The residue was partitioned between CH2Cl2 and water, the organic layer separated, and the aqueous phase re-extracted twice with more CH2Cl2. The combined organic extract was washed with brine, dried over MgSO4 and evaporated in vacuo. Purification of the residue by column chromatography on silica gel furnished the corresponding sulfonate.
  • 15
  • [ 533-58-4 ]
  • [ 26638-43-7 ]
  • [ 2005-10-9 ]
  • [ 136859-40-0 ]
  • 16
  • [ 533-58-4 ]
  • [ 51012-64-7 ]
  • C15H13IO2 [ No CAS ]
  • 17
  • [ 533-58-4 ]
  • [ 456-14-4 ]
  • [ 397-54-6 ]
  • 18
  • [ 533-58-4 ]
  • [ 57297-29-7 ]
  • [ 63359-58-0 ]
  • 19
  • [ 533-58-4 ]
  • [ 28177-52-8 ]
  • [ 71643-66-8 ]
  • 20
  • [ 533-58-4 ]
  • [ 149968-10-5 ]
  • (E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-hydroxyphenyl)propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With N-Methyldicyclohexylamine; t-BuXPhos palladacycle Gen 2; In toluene; at 100℃; for 1h;Inert atmosphere; General procedure: To a flask were added 1-phenylprop-2-en-1-ol (5) (1.196 mL, 9.09 mmol), 2-iodophenol (6) (1 g, 4.55 mmol) and tBuXPhos Pd G2 precatalyst (0.156 g, 0.227 mmol). Then toluene (18 mL) was added to the flask and the solvent was degassed by bubbling N2 through the solution for 15 min. Cy2NMe (2.420 mL, 11.36 mmol) was then added to the flask and the solvent was degassed by bubbling N2 through the solution for an additional 5 min. The reaction mixture was heated to 100 C for 1 h, cooled to r.t. and concentrated to 1/3 volume. The residue was purified by silica gel chromatography to give 0.91 g (88%) of compound 7 as a colorless oil. The spectroscopic data obtained for this compound are in accordance with the previously prepared material.7
  • 21
  • diphenyl(trifluoromethanesulfonato)-λ3-iodane [ No CAS ]
  • [ 533-58-4 ]
  • [ 34883-46-0 ]
  • 22
  • [ 533-58-4 ]
  • [ 4265-25-2 ]
  • 23
  • [ 533-58-4 ]
  • [ 83790-87-8 ]
  • 24
  • [ 533-58-4 ]
  • [ 160976-02-3 ]
  • C18H10BrI3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 135℃; for 12h;Inert atmosphere; In a nitrogen atmosphere, add 2.6-difluoro-p-bromoiodobenzene (0.32 g, 1.01 mmol),o-iodophenol (0.88g, 4.00mmol) and potassium carbonate (0.552mg, 4.00mmol),Then 15 mL of NMP (N-methylpyrrolidone) was added, and the reaction was carried out at 135 C for 12 hours;After the reaction was completed, it was filtered and washed three times with petroleum ether. The organic solutions were combined and concentrated;The crude product was purified with a silica gel column, the eluent was petroleum ether, and the final product was 0.31 g of a white solid with a yield of 43%;
  • 25
  • [ 381-98-6 ]
  • [ 533-58-4 ]
  • 3-(trifluoromethyl)-2H-1-benzopyran-2-one [ No CAS ]
  • 26
  • [ 533-58-4 ]
  • [ 104190-22-9 ]
  • 1-(2-((2-hydroxyphenyl)ethynyl)phenyl)ethan-1-one [ No CAS ]
 

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