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Chemical Structure| 466639-53-2 Chemical Structure| 466639-53-2
Chemical Structure| 466639-53-2

2-Bromo-1-iodo-4-methoxybenzene

CAS No.: 466639-53-2

4.5 *For Research Use Only !

Cat. No.: A235325 Purity: 97%

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Product Citations

Product Citations

Frey, Brandon L. ; Thai, Phong ; Patel, Lauv ; Powers, David C. ;

Abstract: The design and optimization of novel electrocatalysts requires robust structure-activity data to correlate catalyst structure with electrochem. behavior. Aryl iodides have been gaining attention as metal-free electrocatalysts but exptl. data are available for only a limited set of structures. Herein we report electrochem. data for a family of 70 aryl iodides. Half-peak potentials are utilized as proxies for reduction potentials and reveal that, despite differences in electrochem. reversibility, the potential for one-electron oxidation of 4-substituted aryl iodides to the corresponding iodanyl radicals is well-correlated with standard Hammett parameters. Addnl. data are presented for 3- and 2-substituted aryl iodides, including structures with potentially chelating 2-substituents that are commonly encountered in hypervalent iodine reagents. Finally, potential decomposition processes relevant to the (in)stability of iodanyl radicals are presented. We anticipate that the collected data will advance the design and application of aryl iodide electrocatalysis.

Keywords: hypervalent iodine ; electrochemistry ; linear free-energy relationships ; sustainable catalysis ; oxidation

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 466639-53-2 ]

CAS No. :466639-53-2
Formula : C7H6BrIO
M.W : 312.93
SMILES Code : COC1=CC(Br)=C(I)C=C1
MDL No. :MFCD12547848
InChI Key :DIQUDEJWQWDXHP-UHFFFAOYSA-N
Pubchem ID :49757975

Safety of [ 466639-53-2 ]

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

Calculated chemistry of [ 466639-53-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 53.35
TPSA ?

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

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.55
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

3.23
Log Po/w (WLOGP)?

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

3.06
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.

3.44
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

3.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.15

Water Solubility

Log S (ESOL):?

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

-4.19
Solubility 0.0201 mg/ml ; 0.0000641 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-3.1
Solubility 0.25 mg/ml ; 0.0008 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

-4.31
Solubility 0.0153 mg/ml ; 0.000049 mol/l
Class?

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

Moderately 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

Yes
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.

-5.92 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<0.0
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)

2.32

Application In Synthesis of [ 466639-53-2 ]

* 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 [ 466639-53-2 ]

[ 466639-53-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 466639-53-2 ]
  • [ 97308-23-1 ]
  • [ 1273546-88-5 ]
  • 2
  • [ 466639-53-2 ]
  • [ 256652-04-7 ]
  • C17H13BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 5h; (2) Synthesis of Intermediate 1-2 2.5 g (10.0 mmol) of Intermediate 1-1, 3.4 g (11.0 mmol) of 2-bromo-1-iodo-4-methoxy benzene, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 2.1 g (15.0 mmol) of K2CO3 were dissolved in 40 mL of a mixed solution of THF and H2O (2:1 by volume) and stirred at about 80 C. for about 5 hours. After the resulting reaction solution was cooled down to ambient temperature, 40 mL of water was added thereto, followed by extraction three times with 50 mL of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified by silica gel column chromatography to obtain 2.3 g of Intermediate 1-2 (Yield: 72%). This compound was identified by LC-MS. C17H13BrO M+ 313.1
  • 3
  • [ 466639-53-2 ]
  • [ 172732-52-4 ]
  • 2'-bromo-4'-methoxy-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]
 

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Technical Information

Categories

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[ 466639-53-2 ]

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