39224-65-2|4,5-Dichloro-2-nitrophenol| Ambeed

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Quality Control of [ 39224-65-2 ] Purity: 97% SDS Specification

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Product Details of [ 39224-65-2 ]

CAS No. :	39224-65-2
Formula :	C₆H₃Cl₂NO₃
M.W :	208.00
SMILES Code :	OC1=C(C=C(Cl)C(Cl)=C1)[N+]([O-])=O
MDL No. :	MFCD09836170
InChI Key :	CEFFUJIHZMPDID-UHFFFAOYSA-N
Pubchem ID :	38248

Safety of [ 39224-65-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H315-H317-H318-H410
Precautionary Statements:	P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Computational Chemistry of [ 39224-65-2 ] 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	3.0
Num. H-bond donors	1.0
Molar Refractivity	47.31
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.58
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	3.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.61
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.	1.48
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	0.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.36
Solubility	0.0918 mg/ml ; 0.000441 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.	-4.1
Solubility	0.0164 mg/ml ; 0.0000788 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	-2.44
Solubility	0.752 mg/ml ; 0.00361 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.	-5.4 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	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)	1.93

Application In Synthesis of [ 39224-65-2 ]

* 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 [ 39224-65-2 ]

[ 39224-65-2 ] Synthesis Path-Downstream 1~35

1
[ 39224-65-2 ]
[ 28443-57-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron; acetic acid; In water; at 50℃; for 2.0h;	2-Amino-4,5-dichlorophenol To a stirred solution of <strong>[39224-65-2]4,5-dichloro-2-nitrophenol</strong> (15 g, 72 mmol) in acetic acid (150 mL) and water (450 mL), iron powder (16 g, 285 mmol) was added in portions. The resulting mixture was stirred at 50 C. for 2 h. The mixture was allowed to cool to room temperature, filtered, and the cake was rinsed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was washed with water, NaHCO3 (aq.) and brine, dried over Na2SO4 and concentrated in vacuo to afford the desired product (10 g, 78%).
54%	With iron; ammonium chloride; In ethanol; water; at 90℃; for 2.0h;	To a solution of <strong>[39224-65-2]4,5-dichloro-2-nitrophenol</strong> (1.5g, 7.2lmmol) in EtOH (2OmL) were added NH4CI (1.93g, 36.lmmol), Fe powder (2.Og, 36.lmmol) and H20 (5.OmL). The reaction mixture was stirred at 90 00 for 2h. The TLC showed reaction to be complete. Reaction mixture was cooled to room temperature and filtered through a celite bed. The filtrate was concentrated, diluted with H20 (25mL) and extracted with EtOAc (3x5OmL). The organics were dried (Na2504), filtered and concentrated under reduced pressure The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 25% EtOAc in hexane to afford 2-amino-4,5- dichlorophenol as yellow solid. Yield: 700 mg (54%); (MS (ESI-) for CHNOS m/z 176.13 [M-H].1H NMR (400 MHz, DMSO-d6): 9.73 (bs, 1H), 6.71-6.74 (m, 2H),4.95 (bs, 2H).
	With ammonium hydroxide; In water;	106 g of 9A was suspended in 636 ml of water. 233 ml of ammonium hydroxide was added. 239.2 g of sodium dithionite was added over a period of about two hours at such a rate that the temperature of the reaction mixture was kept at about 50 C. The mixture was stirred at room temperature for two hours. The solid product was filtered, and extracted with methanol. Evaporation of the solvent from the extract gave 3,4-dichloro-6-aminophenol (9B).

References: [1]Journal of Organic Chemistry,1996,vol. 61,p. 3289 - 3297.
[2]Patent: US2014/288045,2014,A1 .Location in patent: Paragraph 0456.
[3]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119.
[4]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 81.
[5]Journal of the Chemical Society,1956,p. 4727,4730.
[6]Journal of Biological Chemistry,1952,vol. 194,p. 729,734.
[7]Patent: US4180572,1979,A .

2
[ 39224-65-2 ]
[ 98141-37-8 ]

References: [1]Nippon Kagaku Zasshi,1958,vol. 79,p. 1323,1325.
Chem.Abstr.,1961,p. 434.

3
[ 6306-39-4 ]
[ 39224-65-2 ]

References: [1]Journal of the Brazilian Chemical Society,2013,vol. 24,p. 1146 - 1159.
[2]Journal of Biological Chemistry,1952,vol. 194,p. 729,734.

4
[ 95-77-2 ]
[ 39224-65-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sulfuric acid; nitric acid; In dichloromethane; at -15 - 0℃; for 1.33h;	4,5-Dichloro-2-nitrophenol To a solution of 3,4-dichlorophenol (30 g, 185 mmol) in DCM (300 mL) at -15 C., sulfuric acid (24 g, 278 mmol) was added. To this mixture, nitric acid (19 g, 194 mmol) was added dropwise (over 20 min) and the temperature was controlled between -15 C. to -5 C. The resulting mixture was stirred at 0 C. for 1 h. The mixture was poured into ice and extracted with ethyl acetate. The combined organic layer was washed with water, saturate NaHCO3 aqueous solution and brine, dried over Na2SO4 and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=100:1) to afford the desired product (16 g, 42% yield) as a solid.
39%	With sulfuric acid; nitric acid; In dichloromethane; at 0℃; for 0.5h;	To a solution of 3,4-dichiorophenol (3g, 18.4lmmol) and concentrated H2S04 (1.56 mL, 27.6mmol) in DCM (50 mL) at 0 00 was added fuming HNO3 (1.2mL, 18.4lmmol) dropwise. The reaction mixture was stirred at 0 00 for 30 minutes. The TLC showed reaction to be complete. Reaction was cooled to room temperature, quenched with ice-cold water (25mL) and extracted with DCM (3x25mL). The organics were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel (100-200 mesh), eluting with 2% EtOAc in hexane to afford 4,5-dichloro-2-nitrophenol as yellow solid. Yield: 1.5g (39%); (MS (ESI-) for CHNOS m/z 205.9 [M-H].1H NMR (400 MHz, CDCI3): 10.46 (bs, 1H), 8.23 (5, 1H), 7.33 (5, 1H).
38%	With nitric acid; acetic acid; at 20 - 40℃; for 1.0h;	General procedure: An appropriate phenol (3) (150 mmol) was dissolved in glacial acetic acid (50 mL), and the solution was stirred and maintained at 40 C. Then, a solution containing 11 mL of 65% HNO3 and 30 mL of glacial acetic acid was added drop wise over 15 min. The mixture was stirred at r.t. for 45 min and poured into ice-water (400 mL). The aqueous mixture was extracted four times with CHCl3 (100 mL). Next, the organic phases were collected, dried with Na2SO4, evaporated and purified by column chromatography (4a, 4c, 4e) or crystallisation from ethanol (4b). Compound 4d was used for the next step without further purification [17].

With sulfuric acid; nitric acid; In dichloromethane; at 0 - 5℃; for 0.5h;

A 250 mL roundbottom flask charged with 3, 4-dichlorophenol (3.053 g, 18.7 mmol) in 50 mL CH2Cl2 was cooled to 0C in an ice bath. To the stirred solution was added concentrated H2SO4 (1.56 mL, 28.1 mmol). The solution became turbid. EPO <DP n="77"/>To this mixture was added concentrated HNO3 (1.2 mL, 18.7 mmol) , dropwise and carefully to maintain a temperature below 5C. The reaction was stirred for 30 min at O0C, then cooled with an ice bath and quenched with 150 mL H2O. The layers were separated and the aqueous layer was extracted once with 35 mL CH2Cl2. The combined organics . were dried over anhydrous Na2SO4, concentrated under vacuum and purified using flash chromatrography (10% EtOAc/hexanes as eluent) to yield the desired nitrophenol as a bright yellow solid (1.793 g) .

References: [1]Patent: US2014/288045,2014,A1 .Location in patent: Paragraph 0455.
[2]Synthesis,2004,p. 3043 - 3046.
[3]Journal of Organic Chemistry,1996,vol. 61,p. 3289 - 3297.
[4]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 81.
[5]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119.
[6]Patent: WO2006/105262,2006,A1 .Location in patent: Page/Page column 75; 76.

5
[ 99-54-7 ]
[ 619-08-9 ]
[ 39224-65-2 ]
[ 28165-60-8 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 4199 - 4208.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 24 6,7-Dichlorothieno[3,4-b](1,5]benzoxazepine-10(9H)-one A 16.3 g. portion of 3,4-dichlorophenol is dissolved in 75 ml. of acetic acid, then 5.0 ml. of concentrated nitric acid is added dropwise while the temperature of the solution is maintained between 10-18 C. The solution is stirred an additional 1/2 hour at 10 C., then is poured into 300 ml. of ice water and stirred for 1/2 hour. The product is collected by filtration and dried in vacuo at 50 C. to a melt. The product is extracted with methylene chloride then is concentrated to an oil. The oil is allowed to stand overnight to form brown crystals. The crystals are treated with 250 ml. of water and steam distilled with the addition of 3 additional 250 ml. portions of water. The distillate is extracted with methylene chloride, dried over anhydrous sodium sulfate and concentrated to provide a yellow solid which is recrystallized from 75 ml. of 70% aqueous ethanol to yield 5.47 g. of 2-nitro-4,5-dichlorophenol in 2crops.

7
[ 39224-65-2 ]
[ 16420-13-6 ]
dimethyl-thiocarbamic acid O-(4,5-dichloro-2-nitro-phenyl) ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2589 - 2591.

8
[ 39224-65-2 ]
[ 100-39-0 ]
[ 842117-32-2 ]

References: [1]Synthesis,2004,p. 3043 - 3046.

9
[ 109-01-3 ]
[ 39224-65-2 ]
4-chloro-5-(4-methyl-piperazin-1-yl)-2-nitro-phenol [ No CAS ]