28177-52-8|2-Chloro-6-iodophenol| Ambeed

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Quality Control of [ 28177-52-8 ] Purity: 95% SDS Specification

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Product Details of [ 28177-52-8 ]

CAS No. :	28177-52-8
Formula :	C₆H₄ClIO
M.W :	254.45
SMILES Code :	OC1=C(Cl)C=CC=C1I
MDL No. :	MFCD15833001
Boiling Point :	No data available
InChI Key :	FQFHAEFUBKAIAH-UHFFFAOYSA-N
Pubchem ID :	11470820

Safety of [ 28177-52-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 28177-52-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
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	46.19
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.05
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	3.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.65
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.	2.99
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	2.99
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.86
Solubility	0.0353 mg/ml ; 0.000139 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.	-3.18
Solubility	0.167 mg/ml ; 0.000657 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	-3.39
Solubility	0.103 mg/ml ; 0.000405 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	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.	-5.66 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)	2.0

Application In Synthesis of [ 28177-52-8 ]

* 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 [ 28177-52-8 ]

[ 28177-52-8 ] Synthesis Path-Downstream 1~25

1
[ 95-57-8 ]
[ 28177-52-8 ]
[ 116130-33-7 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 2664 - 2667.
[2]Journal of Organic Chemistry,1988,vol. 53,p. 5281 - 5287.
[3]Tetrahedron Letters,2004,vol. 45,p. 8015 - 8018.
[4]Synthetic Communications,2008,vol. 38,p. 3894 - 3902.
[5]Monatshefte fur Chemie,2012,vol. 143,p. 1039 - 1044.

2
[ 533-58-4 ]
[ 28177-52-8 ]

Yield	Reaction Conditions	Operation 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.

References: [1]ACS Catalysis,2018,vol. 8,p. 4033 - 4043.
[2]Canadian Journal of Chemistry,1965,vol. 43,p. 650 - 658.
[3]Patent: WO2009/158467,2009,A2 .Location in patent: Page/Page column 79-80.

3
[ 61370-55-6 ]
[ 95-57-8 ]
[ 28177-52-8 ]

References: [1]Australian Journal of Chemistry,1997,vol. 50,p. 767 - 769.

4
[ 197243-45-1 ]
[ 95-57-8 ]
[ 28177-52-8 ]

References: [1]Australian Journal of Chemistry,1997,vol. 50,p. 767 - 769.

6
[ 417698-23-8 ]
[ 28177-52-8 ]

References: [1]Canadian Journal of Chemistry,2001,vol. 79,p. 1736 - 1746.

7
[ 95-57-8 ]
[ 28177-52-8 ]

References: [1]Canadian Journal of Chemistry,2001,vol. 79,p. 1736 - 1746.

8
[ 13792-07-9 ]
[ 28177-52-8 ]

References: [1]Canadian Journal of Chemistry,2001,vol. 79,p. 1736 - 1746.

9
[ 342600-91-3 ]
[ 28177-52-8 ]
(αR,γS,2S)-4-[(7-chlorobenzofuran-2-yl)methyl]-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-γ-hydroxy-α-(3-pyridinylmethyl)-2-[[(2,2,2-trifluoroethyl)-amino]carbonyl]-1-piperazinepentanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; copper(I) oxide; for 1.5h;Heating / reflux;	(alphaR,gammaS,2S)-4-[(7-chlorobenzofuran-2-yl)methyl]-N-((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)-gamma-hydroxy-alpha-(3-pyridinylmethyl)-2-[[(2,2,2-trifluoroethyl)amino]carbonyl]-1-piperazinepentanamide; [00934] To a solution of the intermediate prepared in Step A (37.4 mg, 0.0620 mmol) in pyridine (1 mL) was added the intermediate prepared in Step D (18.3 mg, 0.0744 mmol), followed by Cu2O (13.3 mg, 0.093 mmol). The mixture was heated to reflux for 1.5 hours, then cooled to ambient temperature and diluted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous NaHCO3 (30 mL), dried (Na2SO4), and concentrated in vacuo. Purification by flash chromatography (10% methanol in ethyl acetate) afforded the title compound as a white solid.

References: [1]Patent: US6642237,2003,B1 .Location in patent: Page/Page column 149.

10
C₁₂H₁₈ClIO₃Si [ No CAS ]
[ 28177-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.0h;Heating / reflux;	To a solution of the intermediate prepared in Step C (2.60 g, 6.76 mmol) in THF (20 mL) was added tetrabutylammonium fluoride (13.5 mL of a 1.0 M solution in THF, 13.5 mmol). The reaction was heated to reflux for 2 hours, then cooled to ambient temperature and poured onto ethyl acetate (100 mL). The resulting suspension was filtered through celite. The liquid was then washed with water (100 mL×2) and brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (2% ethyl acetate in hexane) afforded the title compound.

References: [1]Patent: US6642237,2003,B1 .Location in patent: Page/Page column 148-149.

11
[ 95-57-8 ]
[ 28177-52-8 ]
[ 15459-49-1 ]
[ 116130-33-7 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 2664 - 2667.

12
[ 110-87-2 ]
[ 28177-52-8 ]
[ 1202677-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium p-toluenesulfonate; In dichloromethane; at 20.0℃;	2-(2-Chloro-6-iodophenoxy)tetrahydro-2H-pyran Error. Objects cannot be created from editing field codes.A solution of 2-chloro-6-iodo-phenol (4.46 g) and pyridinium/?-toluenesulfonate (47 mg) was stirred in 80 mL of dry dichloromethane and 3,4-dihydro-2H-pyran (1.89 g) was added dropwise at room temperature. The mixture was stirred at room temperature for 24 h. The solvent was removed and the residue was purified by silica gel flash chromatography eluting with 20% ethyl acetate in heptane to give 2-(2-chloro-6- iodophenoxy)tetrahydro-2H-pyran (1.78 g) as a white solid. 1H NMR (300 MHz, CDCl3/TMS) delta 7.69 (dd, J= 8.1, 1.5 Hz, IH), 7.34 (dd, J= 7.8, 1.8 Hz, IH), 7.64 (dd, J = 8.1, 7.8 Hz, IH), 5.44 (m, IH), 4.35 (m, IH), 3.61 (m, IH), 2.21-1.89 (m, 6H). 13C NMR (75 MHz, CDCI3/TMS) delta 153.92, 138.65, 131.26, 127.95, 126.35, 103.02, 93.34, 64.14, 30.89, 25.42, 19.30.

References: [1]Patent: WO2009/158467,2009,A2 .Location in patent: Page/Page column 80.

13
[ 533-58-4 ]
[ 28177-52-8 ]
[ 71643-66-8 ]

References: [1]Organic Letters,2016,vol. 18,p. 5476 - 5479.
[2]Organic Letters,2016,vol. 18,p. 5476 - 5479.

14
[ 4971-56-6 ]
[ 28177-52-8 ]
7-chloro-1H-2,8-dioxacyclopenta[a]inden-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With 1-butyl-3-methylimidazolium hydroxide; In water; at 20.0℃; for 7.0h;Green chemistry;	General procedure: A mixture of 2-iodophenol 1 (2.0 mmol), tetronic acid 2 (2.0 mmol), water 3 ml and [bmIm]OH (10 mol%) was stirred at room temperature for 5 h. After completion of reaction as indicated by TLC, 20 mL of water was added to the reaction mixture and stirred well. The product was extracted with EtOAc (3 * 20 mL). The combined organic layer were dried over anhydrous Na2SO4 to afford the crude product and recrystallized from ethanol to obtain analytically pure compound 4 (75-90%). After isolation of the product, the remaining aqueous layer containing the ionic liquid was washed with ether (2x10 mL) to remove organic impurity and filtered. The filtrate was extracted with dichloro methane (2 * 10 mL), dried over MgSO4 and evaporated under reduced pressure to afford [bmIm]OH, which was reused thrice in subsequent runs without further purification.

References: [1]Tetrahedron Letters,2017,vol. 58,p. 4169 - 4173.

15
[ 28177-52-8 ]
C₁₂H₆BrClO [ No CAS ]

References: [1]Patent: KR2018/10167,2018,A .

16
[ 28177-52-8 ]
C₂₀H₉ClN₂O [ No CAS ]

References: [1]Patent: KR2018/10167,2018,A .

17
(2-bromo-6-fluorophenyl)boronic acid [ No CAS ]
[ 28177-52-8 ]
C₁₂H₇BrClFO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12.0h;Reflux; Inert atmosphere;	In a nitrogen atmosphere,(2-bromo-6-fluorophenyl) boronic acid (30.0 g, 137 mmol,(30A) and <strong>[28177-52-8]6-chloro-2-iodophenol</strong> (43.6 g, 150 mmol, Formula 30B) were placed in 400 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (56.8 g, 411 mmol) was dissolved in 150 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (4.8 g, 4 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, and the organic layer and the water layer were separated, and the organic layer was distilled off under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. Then, the organic layer was dried and then placed in 200 ml of dimethylformamide, followed by stirring. Potassium carbonate (56 g, 140 mmol) was then added and refluxed. After 2 hours, the temperature was lowered to room temperature and the reaction solution was reprecipitated in water, followed by stirring for 1 hour and then filtration. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethanol. The resulting solid was filtered and dried to give Intermediate 1 (18 g, 50%).Formula 30A was purchased from alfa aesar, and 30B was purchased from Oakwood.

References: [1]Patent: KR2018/10167,2018,A .Location in patent: Paragraph 0370-0373.

18
[ 28177-52-8 ]
[ 1202677-80-2 ]

References: [1]Patent: WO2009/158467,2009,A2 .
[2]Patent: WO2009/158467,2009,A2 .

19
[ 28177-52-8 ]
[ 1202677-81-3 ]