858854-82-7|3-Chloro-2-iodophenol| Ambeed

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Quality Control of [ 858854-82-7 ] Purity: 97% SDS Specification

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Product Details of [ 858854-82-7 ]

CAS No. :	858854-82-7
Formula :	C₆H₄ClIO
M.W :	254.45
SMILES Code :	OC1=CC=CC(Cl)=C1I
MDL No. :	MFCD08166414
Boiling Point :	No data available
InChI Key :	CBGCAUCBOPFLFN-UHFFFAOYSA-N
Pubchem ID :	12175702

Safety of [ 858854-82-7 ]

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

Computational Chemistry of [ 858854-82-7 ] 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.	1.89
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	2.84
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	2.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.7
Solubility	0.0508 mg/ml ; 0.000199 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.	-2.92
Solubility	0.304 mg/ml ; 0.00119 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.	-5.84 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)	1.97

Application In Synthesis of [ 858854-82-7 ]

* 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 [ 858854-82-7 ]

[ 858854-82-7 ] Synthesis Path-Downstream 1~35

1
[ 56962-00-6 ]
[ 858854-82-7 ]

References: [1]Journal of the Chemical Society,1930,p. 1419,1423.

2
[ 858854-82-7 ]
4,6-dibromo-3-chloro-2-iodo-phenol [ No CAS ]

References: [1]Journal of the Chemical Society,1931,p. 2268,2271.

3
5-chloro-6-iodo-phenol-disulfonic acid-(2.4) [ No CAS ]
[ 858854-82-7 ]

References: [1]Journal of the Chemical Society,1930,p. 1419,1423.

4
[ 858854-82-7 ]
[ 7732-18-5 ]
[ 7726-95-6 ]
4,6-dibromo-3-chloro-2-iodo-phenol [ No CAS ]

References: [1]Journal of the Chemical Society,1931,p. 2268,2271.

5
[ 863870-77-3 ]
[ 858854-82-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ethanol; sodium hydroxide; at 25℃; for 2h;Inert atmosphere; Reflux;	(c) Step 3 Sodium hydroxide (32.0 g, 800 mmol) was added at 25 C. to 400 mL of an ethanol solution of 3-chloro-2-iodophenyl N,N-diethylcarbamate (57.0 g, 161 mmol), and the reaction solution was heated and refluxed for two hours. The ethanol was distilled off under reduced pressure, and the residue was dissolved in 400 mL of water and extracted by petroleum ether. The water layer was neutralized by 2N hydrochloric acid, and extracted by ethyl acetate. The combined organic layers were washed with (saturated) brine, dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3-chloro-2-iodophenol (41.0 g, quantitative). 1H NMR (400 MHz, CDCl3) delta 5.58 (brs, 1H), 6.90 (dd, J=1.2, 8.4 Hz, 1H), 7.06 (dd, J=1.2, 8.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H).
		Carbamate 185 (10 g, 28 mmol, 1 eq) was treated with sodium hydroxide (11 g, 283 mmol, 10 eq) in refluxing ethanol (140 mL). After 14 h, the solution was allowed to cool to rt, acidified with HCl 6N then extracted with DCM (3×60 mL). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (Hexane/DCM 0% to 100%) to obtain 186 an oil (3.75 g, 15 mmol). Yield 52%.

References: [1]Patent: US2017/145005,2017,A1 .Location in patent: Paragraph 0368; 0375; 0376; 0377.
[2]Journal of Organic Chemistry,2005,vol. 70,p. 6548 - 6551.
[3]Journal of Organic Chemistry,2007,vol. 72,p. 5113 - 5118.
[4]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3860 - 3864.
[5]Journal of Organic Chemistry,2011,vol. 76,p. 3416 - 3437.
[6]Patent: US2008/114167,2008,A1 .Location in patent: Page/Page column 172.

6
[ 858854-82-7 ]
[ 536-74-3 ]
[ 344562-15-8 ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 6548 - 6551.

7
[ 858854-82-7 ]
[ 693-02-7 ]
2-butyl-4-chlorobenzo[b]furan [ No CAS ]

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 6548 - 6551.

8
[ 5292-43-3 ]
[ 858854-82-7 ]
[ 945470-02-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In acetone; for 5h;Inert atmosphere; Reflux;	(d) Step 4 Potassium carbonate (26.7 g, 194 mmol) and tert-butyl bromoacetate (34.6 g, 177 mmol) were added to 400 mL of an acetone solution of <strong>[858854-82-7]3-chloro-2-iodophenol</strong> (41.0 g, 161 mmol), and heated and refluxed for five hours. The reaction solution was filtered, and the crude product obtained by concentrating the filtrate was purified by silica gel chromatography (ethyl acetate/petroleum ether), and tert-butyl 2-(3-chloro-2-iodophenoxy)acetate (58.0 g, 97%) was obtained. 1H NMR (400 MHz, CDCl3) delta 1.50 (s, 9H), 4.61 (s, 2H), 6.58 (dd, J=1.2, 8.0 Hz, 1H), 7.15 (dd, J=1.2, 8.0 Hz, 1H), 7.23 (t, J=8.0 Hz, 1H).

References: [1]Patent: US2017/145005,2017,A1 .Location in patent: Paragraph 0368; 0378; 0379; 0380.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 5113 - 5118.
[3]Journal of Medicinal Chemistry,2011,vol. 54,p. 7299 - 7317.

9
[ 13154-24-0 ]
[ 858854-82-7 ]
[ 945470-03-1 ]