452-79-9|2-Fluoro-1-iodo-4-methylbenzene| Ambeed

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Quality Control of [ 452-79-9 ] Purity: 97% SDS Specification

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Product Details of [ 452-79-9 ]

CAS No. :	452-79-9
Formula :	C₇H₆FI
M.W :	236.03
SMILES Code :	CC1=CC=C(I)C(F)=C1
MDL No. :	MFCD00143162
InChI Key :	XVHYSMVSLDIUCM-UHFFFAOYSA-N
Pubchem ID :	2774524

Safety of [ 452-79-9 ]

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

Computational Chemistry of [ 452-79-9 ] Show Less

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	0.0
Molar Refractivity	44.08
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.29
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.04
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.16
Log P_o/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.	3.95
Log P_o/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	3.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.71
Solubility	0.0458 mg/ml ; 0.000194 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.	-2.71
Solubility	0.465 mg/ml ; 0.00197 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	-4.02
Solubility	0.0225 mg/ml ; 0.0000953 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	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.	-5.58 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)	1.86

Application In Synthesis of [ 452-79-9 ]

* 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 [ 452-79-9 ]

[ 452-79-9 ] Synthesis Path-Downstream 1~35

1
[ 352-70-5 ]
[ 452-79-9 ]
[ 66256-28-8 ]

References: [1]Journal of the Indian Chemical Society,1944,vol. 21,p. 112,114.

2
[ 452-79-9 ]
[ 10218-02-7 ]
[ 200001-75-8 ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 673 - 679.

3
[ 452-79-9 ]
[ 581101-42-0 ]

References: [1]Molecules,2004,vol. 9,p. 405 - 426.

4
[ 452-79-9 ]
[ 581101-44-2 ]

References: [1]Molecules,2004,vol. 9,p. 405 - 426.

5
[ 452-79-9 ]
[ 581101-45-3 ]

References: [1]Molecules,2004,vol. 9,p. 405 - 426.

6
[ 452-79-9 ]
(R)-3,3,3-Trifluoro-N-[(S)-2-(2-fluoro-4-methyl-phenyl)-1-hydroxymethyl-ethyl]-2-methoxy-2-phenyl-propionamide [ No CAS ]

References: [1]Molecules,2004,vol. 9,p. 405 - 426.

7
[ 452-79-9 ]
(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-acetylamino-3-(2-fluoro-4-methyl-phenyl)-propyl ester [ No CAS ]

References: [1]Molecules,2004,vol. 9,p. 405 - 426.

8
[ 452-79-9 ]
7-(2-Fluoro-4-methyl-phenyl)-7-phenyl-bicyclo[2.2.1]heptane [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 673 - 679.

9
[ 452-79-9 ]
7-(2-fluoro-4-methylphenyl)-7-(4-methoxyphenyl)norbornane [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 673 - 679.

11
(5R)-2-(trans-4-hydroxycyclohexyl)-2,7-diaza-spiro[4.5]decan-1-one [ No CAS ]
[ 452-79-9 ]
(5R)-7-(2-fluoro-4-methylphenyl)-2-(trans-4-hydroxycyclohexyl)-2,7-diaza-spiro[4.5]decan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 18-crown-6 ether; johnphos; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In tert-butyl alcohol; at 20℃;	Example 180 (5R)-7-(2-Fluoro-4-methylphenyl)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-l- one H A mixture of (5R)-2-(fralphar°-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-l-one (20 mg, 0.00007 mol, this compound was prepared by using procedures analogous to those described in example 1, steps 1-5), 4-methyl-2-fluoro-l-iodobenzene (21 mg, 0.00009 mol), sodium tert-bvAoxide (9.98 mg, 0.000104 mol), 1,4,7,10,13,16-hexaoxacyclooctadecane (27.4 mg, 0.000104 mol) , 2-(di- tert-butylphosphino)biphenyl (0.8 mg, 0.000003 mol) , tris(diben2ylideneacetone)dipalladium(0) (1 mg, 0.000001 mol), in tert-butyl alcohol (1.0 mL, 0.010 mol) was stirred at rt for 18. The crude product was purified by prep-HPLC to afford the desired product. . LC-MS: 361.1 (MfH)+.

References: [1]Patent: WO2006/53024,2006,A2 .Location in patent: Page/Page column 119.

12
[ 475058-41-4 ]
[ 452-79-9 ]
1-(2-fluoro-4-methylphenyl)piperidin-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium phosphate;copper(l) iodide; In ethylene glycol; butan-1-ol; at 100℃;	A mixture of (3S)-piperidin-3-ol hydrochloride (0.50 g, 0.0036 mol), 2-fluoro-l-iodo-4- methylbenzene (1.03 g, 0.00436 mol), copper(I) iodide (140 mg, 0.00073 mol), potassium phosphate (3.08 g, 0.0145 mol), and 1,2-ethanediol (0.810 mL, 0.0145 mol) in 1-butanol (7.28 mL, 0.0796 mol) <n="54"/>was heated at 100 0C under nitrogen for 2 nights. The reaction mixture was treated with water, and then extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was used directly in next step (519 mg, 69%). LCMS (M+H):210.2.

References: [1]Patent: WO2007/89683,2007,A1 .Location in patent: Page/Page column 52-53.

13
[ 452-79-9 ]
[ 1022931-83-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; for 20h;Heating / reflux;	A mixture of <strong>[452-79-9]3-fluoro-4-iodotoluene</strong> (2.26g, 9.58mmol), N-bromosuccinimide (2.03g, 11.49mmol) and benzoyl peroxide (5mol%, 116mg, 0.48mmol) in carbon tetrachloride (5ml) was stirred at reflux for 20 hours, cooled, diluted with dichloromethane and filtered. The purple coloured filtrate was washed with saturated sodium thiosulphate solution (aq) (20ml). The organic layer was separated, dried over sodium sulphate and the solvent removed by rotary evaporation to give the title compound as a yellow oil (2.58g, 86%).1 H-NMR (250MHz, CDCI3): 4.41 (2H, s), 6.94 (1 H, m), 7.11 (1 H, m), 7.72 (1 H, m).
86%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 20h;Reflux;	A mixture of <strong>[452-79-9]3-fluoro-4-iodotoluene</strong> (2.26 g, 9.58 mmol), N-bromosuccinimide (2.03 g, 11.49 mmol) and benzoyl peroxide (5 mol %, 116 mg, 0.48 mmol) in carbon tetrachloride (5 ml) was stirred at reflux for 20 hours, cooled, diluted with dichloromethane and filtered. The purple coloured filtrate was washed with saturated sodium thiosulphate solution (aq) (20 ml). The organic layer was separated, dried over sodium sulphate and the solvent removed by rotary evaporation to give the title compound as a yellow oil (2.58 g, 86%).1H-NMR (250 MHz, CDCl3): delta 7.72 (1H, m), 7.11 (1H, m), 6.94 (1H, m), 4.41 (2H, s).
86%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 20h;Reflux;	N-Bromosuccinimide (2.63g, 14.78mmol) and benzoylperoxide (0.20g, 0.62mmol) were added to a solution of <strong>[452-79-9]3-fluoro-4-iodotoluene</strong> (2.90g, 12.29mmol) in 7mL of tetrachloromethane. The resulting solution was refluxed for 20h. Thereafter, the reaction was allowed to cool to room temperature and was then diluted with 30mL of CH2Cl2. The solid phase was filtered off and the filtrate was washed with 30mL of a saturated solution of sodium thiosulphate. The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (AcOEt/PE 2:98), giving 3.45g (86%) of 8 as a white solid. Rf=0.76 (AcOEt/PE 5:95); mp=46-48C. 1H NMR (600MHz, CDCl3) delta 7.71 (m, 1H), 7.11 (m, 1H), 6.94 (m, 1H), 4.41 (s, 2H); 13C NMR (150MHz, CDCl3) delta 161.0 (J=246.5Hz), 140.6 (J=7.6Hz), 139.9 (J=1.3Hz), 126.4 (J=3.2Hz), 116.4 (J=24.5Hz), 81.3 (J=25.6Hz), 31.5; 19F (564MHz, CDCl3) delta -92.9 (t, J=7.3Hz). Anal. calcd for C7H5BrFI: C, 26.70; H, 1.60; found: C, 26.70; H, 1.58.

References: [1]Patent: WO2008/110566,2008,A1 .Location in patent: Page/Page column 31.
[2]Patent: US2010/137276,2010,A1 .Location in patent: Page/Page column 21.
[3]Journal of Fluorine Chemistry,2015,vol. 178,p. 202 - 207.

14
[ 1161838-12-5 ]
[ 452-79-9 ]
[ 1161838-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; tetrabutyl ammonium fluoride; bis[2-(diphenylphosphino)phenyl] ether;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; toluene; at 100℃;	Step 7: The product from the previous step was dissolved in dry toluene (8mL) under argon. A portion of this stock solution (ImL) was added to a reaction-vial in a Mettler-Toledo Bohdan block using an atmosphere of argon to exclude air. 2-Fluoro-l-iodo-4-methyl-benzene (0.33mmol; prepared from 2-fluoro-4-methyl-phenylamine according to a general literature procedure [S. E. Tunney and J. K. Stille, J. Org. Chem., 52, 748-53 (1987)]) was added as a toluene solution (ImL) followed by 0.5mL of a freshly prepared toluene stock of solution of <n="18"/>tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) and bis[(2-diphenyl- phosphanyl)phenyl] ether DPEphos (corresponding to 0.3 equivalents palladium and 0.6 equivalents DPEphos). Potassium t°t-butoxide (0.66mmol) was added followed by tetra-n- butyl ammonium fluoride (TBAF; 1.0M in THF; 80 microliter). The mixture was stirred at 1000C overnight under argon. Next morning, the volatiles were removed using a Genevac instrument. The residue was dissolved in methanol (4mL) and loaded onto a VacMaster SCX- column (activated with 10% acetic acid in methanol). The product was eluted with acetonitrile. The volatiles were removed in vacuo. The residue was dissolved in methanol (1.5mL) and 4M HCl in diethyl ether (1.5mL) was added. The mixture was shaken at room temperature over the weekend before the volatiles were removed in vacuo. The residue was dissolved in dimethyl sulfoxide (0.18mL) and filtered. A few drops of 20% acetonitrile in water were added, and the mixture was filtered again. The product was isolated by preparative LC/MS as described, concentrated in vacuo, and the product was dissolved in dimethyl sulfoxide (0.78mL) to give a 1OmM solution. LC/MS-data: Method 14, retention time (UV) 2.152 min; UV-purity 79.5%; ELS-purity 100%; mass observed 337.407.

References: [1]Patent: WO2009/76961,2009,A1 .Location in patent: Page/Page column 16; 17.

15
[ 1161838-24-9 ]
[ 452-79-9 ]
C₂₁H₂₂F₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; bis[2-(diphenylphosphino)phenyl] ether;tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 0℃; for 3h;Heating / reflux;	Step 7: The product from the previous step was added to an ice-cooled suspension of potassium tert-butoxide (95.4g) in toluene (2.8L) over ~2h. Then l-bromo-2-fiuoro-4-methyl- benzene (12Ig), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3;1.7g) and bis(2-diphenyl- phosphanyl)ether (DPEphos; 2.48g) were added, and the mixture was refiuxed for ~lh. The crude mixture was cooled to room temperature and filtered through silica gel, and concentrated in vacuo to give the crude product (24Og).

References: [1]Patent: WO2009/76961,2009,A1 .Location in patent: Page/Page column 19.

16
[ 452-79-9 ]
[ 107-18-6 ]
2-fluoro-4-methyl-cinnamaldehyde [ No CAS ]

References: [1]Chemical Communications,2010,vol. 46,p. 415 - 417.

17
[ 452-79-9 ]
[ 108-95-2 ]
[ 1448550-00-2 ]

References: [1]RSC Advances,2013,vol. 3,p. 1890 - 1895.

18
[ 452-74-4 ]
[ 452-79-9 ]

Yield	Reaction Conditions	Operation in experiment
13 g		j0167] (13-i) Under dry nitrogen, a solution prepared by dissolving 4-bromo-3-fluorotoluene (10 g) in THF (50 mE) was cooled to -72 C. Then, a 1.6 mol/E n-butyl lithium hexane solution (35 mE) was added at -72 C. to the solution such a rate that the inside temperature was not more than -65 C., followed by thrther stirring at -72 C. for 1 hour. A solution prepared by dissolving iodine (14.8 g) in THF (30 mE) was added at -72 C. to the resultant mixture such a rate that the inside temperature was not more than -60 C., and the temperature was slowly increased to room temperature. Then, a saturated aqueous ammonium chloride solution and hexane were added at room temperature to separate an organic layer, and the organic layer was washed with a 10% aqueous sodium sulfite solution two times and saturated brine in that order, and then dried with sodium sulfate. The sodium sulfate was filtered off, and the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to yield 13.0 g of 3-fluoro-4-iodotoluene as a yellow liquid.

References: [1]Patent: US2014/275577,2014,A1 .Location in patent: Paragraph 0166; 0167.

19
[ 452-79-9 ]
4-(3,4,5-trifluorophenyl)-3-fluorobenzyl bromide [ No CAS ]

References: [1]Patent: US2014/275577,2014,A1 .

20
[ 452-79-9 ]
5-fluoro-4-(3,4,5-trifluorophenyl)phenyl-[2,6-difluoro-4-(4-propylcyclohexyl)phenyloxy]methane [ No CAS ]

References: [1]Patent: US2014/275577,2014,A1 .

21
[ 452-79-9 ]
[ 143418-49-9 ]
4-(3,4,5-trifluorophenyl)-3-fluorotoluene [ No CAS ]