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Chemical Structure| 348-52-7 Chemical Structure| 348-52-7

Structure of 1-Fluoro-2-iodobenzene
CAS No.: 348-52-7

Chemical Structure| 348-52-7

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Synonyms: o-Iodofluorobenzene

4.5 *For Research Use Only !

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Product Details of [ 348-52-7 ]

CAS No. :348-52-7
Formula : C6H4FI
M.W : 222.00
SMILES Code : FC1=CC=CC=C1I
Synonyms :
o-Iodofluorobenzene
MDL No. :MFCD00001031
InChI Key :TYHUGKGZNOULKD-UHFFFAOYSA-N
Pubchem ID :67673

Safety of [ 348-52-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H315-H318
Precautionary Statements:P210-P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P332+P313-P362+P364-P370+P378-P403+P235-P501
Class:9
UN#:3082
Packing Group:

Computational Chemistry of [ 348-52-7 ] 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 0.0
Molar Refractivity 39.12
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.02
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

3.1
Log Po/w (WLOGP)?

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

2.85
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.

3.64
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

3.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.98

Water Solubility

Log S (ESOL):?

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

-3.72
Solubility 0.0419 mg/ml ; 0.000189 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.

-2.77
Solubility 0.379 mg/ml ; 0.00171 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

-3.63
Solubility 0.0516 mg/ml ; 0.000232 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

Low
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.

-5.45 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)

2.2

Application In Synthesis of [ 348-52-7 ]

* 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.

  • Downstream synthetic route of [ 348-52-7 ]

[ 348-52-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 348-52-7 ]
  • [ 6277-17-4 ]
  • 1-fluoro-9-methyl-dibenzoiodolium; iodide [ No CAS ]
  • 2
  • [ 348-52-7 ]
  • [ 6277-17-4 ]
  • 2'-Fluoro-6-methyl-2-nitro-biphenyl [ No CAS ]
  • 4
  • [ 348-52-7 ]
  • [ 172732-52-4 ]
  • [ 400820-15-7 ]
  • 5
  • [ 348-52-7 ]
  • [ 172732-52-4 ]
  • [ 1514-18-7 ]
  • 6
  • [ 2622-63-1 ]
  • [ 348-52-7 ]
  • 2-(2'-fluorobiphenyl-2-yl)-1-methyl-1H-benzoimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium carbonate; triphenylphosphine; In benzene; at 150℃; for 24h;Sealed tube; General procedure: In a 30-mL sealed tube, <strong>[2622-63-1]1-methyl-2-phenylbenzimidazole</strong> (1, 0.25mmol), [RuCl2(p-cymene)]2 (0.0125 mmol), Ph3P (0.075 mmol),K2CO3 (0.50 mmol), and iodoarene (0.25 mmol) were combined inanhydrous benzene (2 mL) under air. The mixture was then stirredat 150 °C for 24 h. The mixture was cooled to r.t., diluted with EtOAc, and filtered through a small pad of Celite. The filtrate was concentrated in vacuo and purified by flash chromatography (silicagel, EtOAc?hexane) to give the analytically pure 2-(biphenyl-2-yl)benzimidazoles.
  • 7
  • [ 348-52-7 ]
  • [ 14135-38-7 ]
YieldReaction ConditionsOperation in experiment
69% With carbon disulfide; cycl-isopropylidene malonate; triethylamine; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; General procedure: A mixture of Meldrum?s acid (1 mmol) and Et3N (2 mmol) in DMF was stirred for 15 min at r.t. Then, CS2 (1 mmol) was added and stirred for 15 min. Then, the obtained mixture was added to a stirred solution of aryl halide (1 mmol) and CuCl (0.1 mmol) in DMF (2 ml), and heated at 100 C for 4h. When the reaction was completed (TLC), the mixture was extracted with CH2Cl2 (3 3ml) and H2O (3ml). The organic layer was separated and dried (Na2SO4) and the solvent was evaporated in vacuo to give the diaryl disulfide. The product was purified by column chromatography on silica gel (EtOAc / Petroleum ether, 1:4).
  • 8
  • [ 599-66-6 ]
  • [ 348-52-7 ]
  • 2-fluorophenyl 4-tolyl sulfide [ No CAS ]
  • 9
  • [ 348-52-7 ]
  • [ 907973-43-7 ]
  • 10
  • [ 348-52-7 ]
  • [ 79-10-7 ]
  • [ 18944-77-9 ]
YieldReaction ConditionsOperation in experiment
87% With triethylamine; In water; at 100℃; for 12h; General procedure: In a typical Heck coupling reaction between iodobenzene and acrylic acid, 10 mmol of iodobenzene and 30 mmol of acrylic acid were mixed with 50 mmol of triethylamine and 10 mL of distill water. The insoluble PdIPN catalyst (2.3 g) was added to the solution, and the reactants were heated in an oil bath at 100 C for 12 h under stirring. After the reaction, the catalysts were filtered, thoroughly washed with water and ethanol (at least three times) and dried in the air for the next round of use. The white product was precipitated out by adding 1 mol/L HCl solution, then separated by centrifugation and filtration, washed repeatedly with cold water, and dried in vacuum for 6 h. The yield from the reaction between iodobenzene and acrylic acid was 87%.
 

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