123158-75-8|4-Chloro-2-iodo-6-nitroaniline| Ambeed

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Quality Control of [ 123158-75-8 ] Purity: 95% SDS Specification

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Product Details of [ 123158-75-8 ]

CAS No. :	123158-75-8
Formula :	C₆H₄ClIN₂O₂
M.W :	298.47
SMILES Code :	NC1=C([N+]([O-])=O)C=C(Cl)C=C1I
MDL No. :	MFCD23115369
InChI Key :	WDQPNLNIJFQQRL-UHFFFAOYSA-N
Pubchem ID :	12143564

Safety of [ 123158-75-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 123158-75-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	57.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.62
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	2.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.44
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.	1.8
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	0.63
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.88

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.82
Solubility	0.045 mg/ml ; 0.000151 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.	-4.07
Solubility	0.0255 mg/ml ; 0.0000853 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-2.98
Solubility	0.316 mg/ml ; 0.00106 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	Yes
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.	-6.06 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.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	4.0 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)	2.56

Application In Synthesis of [ 123158-75-8 ]

* 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 [ 123158-75-8 ]

[ 123158-75-8 ] Synthesis Path-Downstream 1~31

1
[ 123158-75-8 ]
[ 123158-76-9 ]

References: [1]Journal of the Chemical Society,1928,p. 783.
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

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[ 123158-75-8 ]
[ 108-24-7 ]
[ 64-19-7 ]
acetic acid-(4-chloro-2-iodo-6-nitro-anilide) [ No CAS ]

References: [1]Journal of the Chemical Society,1928,p. 783.

3
[ 89-63-4 ]
[ 123158-75-8 ]

Yield	Reaction Conditions	Operation in experiment
69%	With iodine; silver nitrate; In ethanol; at 20℃; for 8h;	(Step 1)Commercially available 4-chloro-2-nitro-phenylamine (17.4 g, 131.5 mmol) was dissolved in ethanol (300 mL), and thereto silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added. The mixture was stirred for 8 hours at room temperature. At the end of reaction, the mixture was filtered using celite and washed with 100 ml of ethylacetate and concentrated. To the concentrate, added water and extracted with ethylacetate. The organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate to give 2-amino-5-chloro-3-nitro-phenyliodide (27.4 g, Yield 69%).1H-NMR (500 MHz, CDCl3); delta 7.94 (s, 1H), 7.75 (s, 1H), 6.48 (br s, 2H), 2.23 (s, 3H)
28%	With Iodine monochloride; In glacial AcOH;	A. Synthesis of 4-chloro-2-iodo-6-nitroaniline: The procedure of Leeson, P. D. et al. (J. Med. Chem. 34:1243-1252 (1991)) was adapted. To a solution of 4-chloro-2-nitroaniline (2.15 g, 12.45 mMol, Aldrich, used as received) in glacial AcOH (16 mL) was added iodine monochloride (2.114 g, 12.90 mMol, Aldrich). The mixture was heated at 120 C. for 5 h, then cooled and poured into ice water (30 g). The precipitate was collected and washed with 10% sodium sulfite solution (20 mL), then it was crystallized from MeOH to give 4-chloro-2-iodo-6-nitroaniline (1.05 g, 28%), as long brown needles, m.p. 134-5 C. NMR (1 H, CDCl3): delta6.660 (s, 2H); 7.906 (d, 1H, J=2.1 Hz); 8.188 (d, 1H, J=1.8 Hz).
	With Iodine monochloride; In acetic acid;	a) A solution of 4-chloro-2-nitroaniline (34.5 g) in acetic acid (500 ml) was refluxed with iodine monochloride (65.0 g) for 7 h with stirring, then was cooled and added to excess water. The precipitate was filtered off, washed with aqueous sodium sulphite and after column chromatography yielded 4-chloro-2-iodo-6-nitroaniline (8.5 g). delta (360 MHz, DMSO-d6) 7.13 (2H, bs, NH2), 8.08 (1H, d, 3-H) and 8.13 (1H, d, 5-H).

References: [1]Chemistry - A European Journal,2003,vol. 9,p. 5323 - 5331.
[2]Patent: US2010/291533,2010,A1 .Location in patent: Page/Page column 57.
[3]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.
[4]Patent: US5514680,1996,A .
[5]Journal of the Chemical Society,1928,p. 783.
[6]Tetrahedron Letters,2009,vol. 50,p. 4423 - 4426.
[7]Journal of Organic Chemistry,2015,vol. 80,p. 10806 - 10816.
[8]Patent: US5270309,1993,A .

4
[ 64-17-5 ]
[ 123158-75-8 ]
[ 110-46-3 ]
[ 123158-76-9 ]

References: [1]Journal of the Chemical Society,1928,p. 783.

5
[ 64-19-7 ]
[ 89-63-4 ]
p-toluenesulfonylacid dichloroamide [ No CAS ]
sodium iodide [ No CAS ]
[ 123158-75-8 ]

References: [1]Journal of the Chemical Society,1928,p. 783.

6
[ 123158-75-8 ]
[ 4637-24-5 ]
N'-(4-chloro-2-iodo-6-nitrophenyl)-N,N-dimethylimidoformamide [ No CAS ]

References: [1]Chemistry - A European Journal,2003,vol. 9,p. 5323 - 5331.

7
[ 123158-75-8 ]
N-(6-chloro-4-iodo-1H-benzimidazol-2-yl)-N,N-dimethylamine [ No CAS ]

References: [1]Chemistry - A European Journal,2003,vol. 9,p. 5323 - 5331.

8
[ 123158-75-8 ]
[ 83171-49-7 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

9
[ 123158-75-8 ]
[ 123157-61-9 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

10
[ 123158-75-8 ]
[ 123157-60-8 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

11
[ 123158-75-8 ]
[ 123158-45-2 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

12
[ 123158-75-8 ]
[ 123158-44-1 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1243 - 1252.

13
[ 88-74-4 ]
[ 123158-75-8 ]

References: [1]Journal of the Chemical Society,1928,p. 783.

14
[ 71-23-8 ]
[ 123158-75-8 ]
[ 153505-43-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;Pb-CaCO3; In tetrahydrofuran;	Example B4 Preparation of 4-chloro-6-iodo-1.2-phenylenediamine 1.5 g of <strong>[123158-75-8]4-chloro-2-iodo-6-nitroaniline</strong> together with 50 ml of tetrahydrofuran and 10 ml of 1-propanol are initially introduced into a stirred autoclave. 5 mg of FeCl2.4H2 O and 0.3 g Pt/Pb-CaCO3 catalyst are added to the solution, and hydrogenation is carried out at 130 C. and 20 bar of hydrogen. After the hydrogenation has come to a standstill, the reaction mixture is cooled to room temperature, the reactor is rendered inert with nitrogen and the catalyst is filtered off. After filtration, the solvent is removed by distillation to give 1.3 g of 4-chloro-6-iodo-1,2-phenylenediamine as a crude product. 1 H-NMR (CDCI3, 300MHz) 3.56 ppm (s, 2H, broad); 3.77 ppm (s, 2H, broad); 6.68 ppm (s, 1H); 7.18 ppm (s, 1H).

References: [1]Patent: US5877340,1999,A .

Yield	Reaction Conditions	Operation in experiment
	With iodine; silver nitrate; In ethanol; at 20℃; for 8h;	General procedure: Commercially available 4-methyl-2-nitro-phenylamine (20 g, 131.5 mmol) was dissolved in ethanol (300 mL), silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. After completion of the reaction, the reaction mixture was filtered through a cellite, washed with 100 mL of ethyl acetate, and concentrated. Water was added to the residue, which was then extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound (29 g, Yield 69%).
	With iodine; silver nitrate; In ethanol; at 20℃; for 8h;	General procedure: Commercially available 4-methyl-2-nitro - phenylamine (20g, 131.5mmol) was dissolved in ethanol (300mL), was added silver nitrate (27g, 157.7mmol) and iodine (40g, 157.7mmol), in It was stirred at room temperature for 8 hours. After completion of the reaction, the Cellite filtration, washing with ethyl acetate 100mL was concentrated. After addition of water and extracted with ethyl acetate. After washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the harvest of the title compound (29g, yield 69%).
	With iodine; silver nitrate; In ethanol; at 20℃; for 8h;	General procedure: Commercially available 4-methyl-2-nitro-phenylamine (20 g, 131.5 mmol) was dissolved in ethanol (300 ml), to which were added silver nitrate (27 g, 157.7 mmol) and iodine (40 g, 157.7 mmol), and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the mixture was filtered through Cellite, washed with ethyl acetate (100 ml), and concentrated. The reactant was added with water, extracted with ethyl acetate, washed with saturated sodium chloride solution, and dried with anhydrous magnesium sulfate to give the title compound (29 g, Yield 69%).

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[ 123158-75-8 ]
[ 2170-06-1 ]
[ 1120334-15-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h;	<strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in <n="51"/>Preparation 19 and l-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 rnL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100C . After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%). 1H-NMR (400HMz, CDCl3); delta 9.78(br s, IH), 8.15(s, IH), 7.78(s, IH),7.38~7.48(m, 5H), 0.26(s, 9H)
87%	With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h;	Preparation 41: 5-Chloro-3-phenyl-7-nitro-1H-indoleStep A: 5-Chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole; <strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78(br s, 1H), 8.15(s, 1H), 7.78(s, 1H), 7.387.48(m, 5H), 0.26(s, 9H)
87%	With triethylamine; lithium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h;	(Step 2)<strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) obtained in Step 1 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL), and thereto palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added. The mixture was heated under stirring for 3 hours at 100 C. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give 5-chloro-7-nitro-3-phenyl-2-trimethylsilyl-1H-indole (1.05 g, Yield 87%).1H-NMR (400 MHz, CDCl3); delta 9.78 (br s, 1H), 8.15 (s, 1H), 7.78 (s, 1H), 7.387.48 (m, 5H), 0.26 (s, 9H)

87%

With palladium diacetate; triethylamine; lithium chloride; In N,N-dimethyl-formamide; at 100℃; for 3h;

<strong>[123158-75-8]2-Amino-5-chloro-3-nitro-phenyliodide</strong> (1.5 g, 4.90 mmol) prepared in Preparation 19 and 1-phenyl-2-trimethylsilylacetylene (4.3 g, 24.50 mmol) were dissolved in DMF (50 mL). Palladium acetate (0.11 g, 0.5 mmol), lithium chloride (0.21 g, 4.90 mmol) and triethylamine (2.48 g, 24.50 mmol) were added thereto, and the mixture was stirred under heating for 3 h to 100 C. After completion of the reaction, water was added to the reaction mixture, which was then extracted with ethyl acetate, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (1.05 g, Yield 87%).

References: [1]Patent: WO2009/25478,2009,A1 .Location in patent: Page/Page column 49-50.
[2]Patent: US2010/197673,2010,A1 .Location in patent: Page/Page column 14.
[3]Patent: US2010/291533,2010,A1 .Location in patent: Page/Page column 57-58.
[4]Patent: KR101511771,2015,B1 .Location in patent: Paragraph 0386-0388.

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[ 931-49-7 ]
[ 123158-75-8 ]
[ 1180556-79-9 ]