34074-22-1|2,6-Dichloro-4-iodophenol| Ambeed

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Quality Control of [ 34074-22-1 ] Purity: 98% SDS Specification

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Product Details of [ 34074-22-1 ]

CAS No. :	34074-22-1
Formula :	C₆H₃Cl₂IO
M.W :	288.90
SMILES Code :	OC1=C(Cl)C=C(I)C=C1Cl
MDL No. :	MFCD00466446
Boiling Point :	No data available
InChI Key :	AIGWECICLKWOIR-UHFFFAOYSA-N
Pubchem ID :	4493083

Safety of [ 34074-22-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 34074-22-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
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	51.2
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.	2.15
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	3.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.3
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.	3.56
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	3.63
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.22

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.26
Solubility	0.0158 mg/ml ; 0.0000548 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.58
Solubility	0.0765 mg/ml ; 0.000265 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	-4.0
Solubility	0.029 mg/ml ; 0.0001 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.	-5.6 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)	2.21

Application In Synthesis of [ 34074-22-1 ]

* 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 [ 34074-22-1 ]

[ 34074-22-1 ] Synthesis Path-Downstream 1~35

1
[ 34074-22-1 ]
[ 946-31-6 ]

References: [1]Journal of the Chemical Society,1912,vol. 101,p. 973.

2
[ 34074-22-1 ]
2,6-dichloro-4-dichloroiodanyl-phenol [ No CAS ]

References: [1]Journal of the Chemical Society,1912,vol. 101,p. 973.

3
2-chloro-4-dichloroiodanyl-phenol [ No CAS ]
[ 34074-22-1 ]

References: [1]Journal of the Chemical Society,1912,vol. 101,p. 973.
[2]Journal of the Chemical Society,1912,vol. 101,p. 973.

4
[ 34074-22-1 ]
[ 77-78-1 ]
[ 71742-42-2 ]

References: [1]Journal of the Chemical Society,1931,p. 1103,1108.
[2]Journal of the Chemical Society. Perkin transactions I,1982,p. 2299 - 2316.

5
[ 87-65-0 ]
[ 34074-22-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dihydrogen peroxide; iodine; In water; for 0.75h;Sonication;	General procedure: General Procedure for Ultrasound-Promoted Iodination of Aromaticand Heteroaromatic Compounds: Hydrogen peroxide 30% (m/v) (4-8 mmol) was added to a suspension of theappropriate aromatic or heteroaromatic compound (1a-q) (2 mmol) and moleculariodine (2-4 mmol) in distilled water (10 mL). The mixture was sonicated and the progressof reaction was monitored by thin-layer chromatography (TLC). Afterward, asaturated sodium thiosulfate aqueous solution (10 mL) was added to the mixture,which was extracted with ethyl acetate (320mL). The organic phase was dried overMgSO4. After filtration, the solvent was evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel using an appropriate eluent,affording the desired product (2a-q).
59%	With N-iodo-succinimide; In methanol; at 20℃; for 1h;	A solution of 2,6-dichlorophenol (10 g, 61.35 mmol, 1.00 equiv) and NIS (27.6 g, 245.33 mmol, 2.00 equiv) in methanol (100 mL) was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was redissolved in 50 mL of ethyl acetate and washed with 3*30 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with petroleum ether (100%) to give 10.5 g (59%) of 2,6-dichloro-4-iodophenol as a yellow solid. 1H-NMR (300 MHz, CDCl3): delta 9.83 (s, 1H), 7.27 (s, 2H) ppm.

References: [1]Patent: WO2006/100026,2006,A1 .Location in patent: Page/Page column 121.
[2]Synthetic Communications,2014,vol. 44,p. 2094 - 2102.
[3]Journal of the Brazilian Chemical Society,2010,vol. 21,p. 770 - 774.
[4]Synthetic Communications,2012,vol. 42,p. 2407 - 2414.
[5]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2936 - 2941.
[6]Journal of Organic Chemistry,2019,vol. 84,p. 4149 - 4164.
[7]Helvetica Chimica Acta,1993,vol. 76,p. 877 - 883.
[8]Patent: US2014/323537,2014,A1 .Location in patent: Paragraph 0339.
[9]Journal of the Chemical Society. Perkin transactions I,1982,p. 2299 - 2316.
[10]Journal of the American Chemical Society,2003,vol. 125,p. 9032 - 9034.
[11]Journal of Organic Chemistry,2009,vol. 74,p. 1124 - 1129.

6
[ 34074-22-1 ]
[ 98033-85-3 ]
[ 107311-60-4 ]

References: [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1306 - 1311.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 4628 - 4633.

7
[ 34074-22-1 ]
[ 148902-82-3 ]
[ 148902-83-4 ]

References: [1]Helvetica Chimica Acta,1993,vol. 76,p. 877 - 883.

8
[ 34074-22-1 ]
[ 120517-43-3 ]
[ 148902-79-8 ]

References: [1]Helvetica Chimica Acta,1993,vol. 76,p. 877 - 883.

9
[ 34074-22-1 ]
[ 54904-42-6 ]
[ 100-02-7 ]
C₁₂H₇Cl₂HgIO [ No CAS ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1975,vol. 24,p. 2334 - 2339.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1975,vol. 24,p. 2447 - 2453.

11
[ 34074-22-1 ]
[ 7697-37-2 ]
[ 946-31-6 ]

References: [1]Journal of the Chemical Society,1912,vol. 101,p. 973.

12
[ 553-90-2 ]
[ 34074-22-1 ]
[ 586413-77-6 ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 9032 - 9034.

13
[ 540-38-5 ]
[ 34074-22-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With diisobutylamine; sulfuryl dichloride; In toluene; at 20 - 70℃; for 1h;Inert atmosphere;	To a solution of 4-iodophenol (5.50 g, 25 mmol) in dry toluene (90 mL) at room temperature was added diisobutylamine (35 muL, 0.2 mmol) under argon atmosphere. The resulting solution was warmed up to 70 C., then SO2Cl2 (6.05 mL, 75 mmol) was slowly added in via a syringe (gas escapes to a balloon). The reaction mixture was stirred at 70 C. for 1 h and allowed to cool to room temperature. Then the reaction mixture was diluted with Et2O and washed with saturated NaHCO3 solution and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The target compound HJ-3-93 [34074-22-1] was isolated as a white solid by flash chromatography on silica gel by using EtOAc:Hexane (1:99) as an eluent. Yield: 7.20 g (99%). 1H NMR (400 MHz, CDCl3) delta 7.53 (s, 2H), 5.81 (brs, 1H); 13C NMR (100 MHz, CDCl3) delta 148.0, 136.4, 122.1, 80.5.

References: [1]Patent: US2016/312033,2016,A1 .Location in patent: Paragraph 0089; 0090.
[2]Organic Letters,2006,vol. 8,p. 4251 - 4254.
[3]Journal of the Chemical Society,1912,vol. 101,p. 973.

14
[ 34074-22-1 ]
[ 5407-04-5 ]
[ 913171-32-1 ]