19337-60-1|3-Iodobenzene-1,2-diol| Ambeed

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Quality Control of [ 19337-60-1 ] Purity: 95+% SDS Specification

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Product Details of [ 19337-60-1 ]

CAS No. :	19337-60-1
Formula :	C₆H₅IO₂
M.W :	236.01
SMILES Code :	OC1=C(O)C(I)=CC=C1
MDL No. :	MFCD18072901
InChI Key :	HUMAHCJCCNMIGP-UHFFFAOYSA-N
Pubchem ID :	18615965

Safety of [ 19337-60-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 19337-60-1 ] 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	2.0
Num. H-bond donors	2.0
Molar Refractivity	43.21
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.46 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.37
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	1.86
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.7
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.	1.75
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	1.87
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.71

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.97
Solubility	0.254 mg/ml ; 0.00108 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.	-2.33
Solubility	1.1 mg/ml ; 0.00467 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	-2.2
Solubility	1.48 mg/ml ; 0.00625 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	No
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.42 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	0.0
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.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 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)	2.12

Application In Synthesis of [ 19337-60-1 ]

* 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 [ 19337-60-1 ]

[ 19337-60-1 ] Synthesis Path-Downstream 1~35

1
[ 138769-92-3 ]
[ 19337-60-1 ]

References: [1]Advanced Synthesis and Catalysis,2007,vol. 349,p. 727 - 739.

2
[ 766-96-1 ]
[ 19337-60-1 ]
[ 934330-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 50℃; for 2.5h;	Dichloropalladium bistriphenylphosphine (0.14 g) and copper (I) iodide (0.036 g) were added to a degassed solution of Intermediate 68 (0.89 g), bromophenyl acetylene (1.02 g) and triethylamine (2.11 mL) in THF (12 ml_). The mixture was heated at 5O0C under nitrogen for 2.5 h. The reaction was allowed to cool and was evaporated in vacuo. The residue was partitioned between DCM and water. The organics were separated using a hydrophobic frit and were evaporated in vacuo. The crude material was purified by ISCO Companion silica <n="64"/>chromatography, eluting with a gradient 0-70percent EtOAc in cyclohexane to give the title compound.1H NMR (d6-DMSO) delta 9.57 (1 H, s), 9.07 (1H, s), 7.61 (2H, d), 7.46 (2H, d), 6.83 (2H, dt),6.04 (1 H, t).

References: [1]Patent: WO2007/71434,2007,A1 .Location in patent: Page/Page column 62-63.

3
[ 25245-33-4 ]
[ 19337-60-1 ]

Yield	Reaction Conditions	Operation in experiment
22%	With boron tribromide; In dichloromethane; at 0 - 20℃; for 3.0h;	1-Iodo-2,3-dimethoxybenzene (0.62 g, 2.35 mmol) obtained in Step A was dissolved in DCM (23 mL) andcooled to 0-5°C. 1M BBr3 (0.276 mL, 7.05 mmol) was slowly added thereto, and the mixture was stirred at room temperaturefor 3 hours. After termination of the reaction, the reaction solution was cooled to -20°C and diluted by slowlyadding ethanol. The mixure was stirred at room temperature for 30 minutes, and saturated NaHCO3 aqueous solutionwas added thereto. The mixture was extracted with DCM. The organic layer was dried with MgSO4, concentrated underreduced pressure and purified by column chromatography (eluent, EtOAc/Hex = 1/4) to obtain the title compound (0.12g, 22 percent).1H NMR (500 MHz, CDCl3) delta 7.18(d, 1H), 6.87(d, 1H), 6.60(t, 1H), 5.64(s, br, 2H)
		To a stirred solution of 1-iodo-2,3-bis(methyloxy)benzene (1.01 g) in dry DCM (6 ml.) under nitrogen at -450C was added a solution of boron tribromide (1M in DCM, 4.24 ml_). After 0.5 h at -450C the cooling bath was removed and the mixture was allowed to stir at room temperature for 1 h. The mixture was then cooled to -90C and water was added dropwise with stirring. The organics were separated using a hydrophobic frit and the aqueous phase was extracted with DCM. The combined organics were evaporated in vacuo to give the title compound. MS calcd for (C6H5IO2 - H)": 235 MS found (electrospray): (M-H)" = 235

References: [1]Journal of Materials Chemistry,2008,vol. 18,p. 400 - 407.
[2]Patent: EP3239143,2017,A2 .Location in patent: Paragraph 0113; 0439.
[3]Patent: WO2007/71434,2007,A1 .Location in patent: Page/Page column 62.
[4]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

4
[ 4292-19-7 ]
[ 19337-60-1 ]
[ 1010685-17-2 ]

References: [1]Journal of Materials Chemistry,2008,vol. 18,p. 400 - 407.

5
[ 626-02-8 ]
[ 19337-60-1 ]
[ 1176877-24-9 ]
[ 132746-89-5 ]

References: [1]Chemical Communications,2009,p. 3633 - 3635.

6
[ 19337-60-1 ]
[ 1444011-09-9 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

7
[ 19337-60-1 ]
[ 1444011-10-2 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

8
[ 19337-60-1 ]
[ 1444011-13-5 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

9
[ 19337-60-1 ]
[ 1444011-03-3 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

10
[ 19337-60-1 ]
[ 1444011-04-4 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

11
[ 19337-60-1 ]
[ 100-39-0 ]
[ 1444011-07-7 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

12
[ 19337-60-1 ]
[ 122-51-0 ]
[ 1444011-08-8 ]

References: [1]Chemical Communications,2013,vol. 49,p. 6167 - 6169.

13
[ 591-50-4 ]
[ 19337-60-1 ]

References: [1]Organic Process Research and Development,2002,vol. 6,p. 525 - 532.

14
[ 19337-60-1 ]
[ 1607814-76-5 ]

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

15
[ 19337-60-1 ]
[ 1607814-79-8 ]

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

16
[ 19337-60-1 ]
[ 1607814-73-2 ]

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

17
[ 19337-60-1 ]
Frutinone C [ No CAS ]

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

18
[ 19337-60-1 ]
11-methoxy-6H,7H-<1>benzopyrano<4,3-b><1>benzopyran-6,7-dione [ No CAS ]

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

19
[ 110-87-2 ]
[ 19337-60-1 ]
[ 1607814-83-4 ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridinium p-toluenesulfonate; In dichloromethane; at 0℃; for 5.0h;Inert atmosphere;	To a solution of <strong>[19337-60-1]3-iodocatechol</strong> (1.22 g, 5.17 mmol, 1.00 equiv) in dry CH2Cl2 (15.5 mL, 3.00 mL/mmol) was added 3,4-dihydro-2H-pyran (567 muL, 6.20 mmol, 1.20 equiv) and pyridinium p-toluenesulfonate (131 mg, 517 mumol, 0.10 equiv) at 0 °C under argon. After being stirred at the same temperature for 5 h, the reaction mixture was quenched with triethylamine at 0 °C. The reaction mixture was concentrated in vacuo and then the resulting residue was purified by column chromatography on silica gel (eluted with hexane/ethyl acetate = 30/1) to THP ether S5 (1.08 g, 3.37 mmol, 65percent) as a colorless oil.

References: [1]Tetrahedron,2014,vol. 70,p. 3452 - 3458.

20
[ 19337-60-1 ]
[ 2411-83-8 ]