16582-38-0|1-Chloro-3-methyl-5-nitrobenzene| Ambeed

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Quality Control of [ 16582-38-0 ] Purity: 98% SDS Specification

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Product Details of [ 16582-38-0 ]

CAS No. :	16582-38-0
Formula :	C₇H₆ClNO₂
M.W :	171.58
SMILES Code :	O=[N+](C1=CC(C)=CC(Cl)=C1)[O-]
MDL No. :	MFCD09955417
Boiling Point :	No data available
InChI Key :	IYHHGLULQDOFGC-UHFFFAOYSA-N
Pubchem ID :	297887

Safety of [ 16582-38-0 ]

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

Computational Chemistry of [ 16582-38-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	45.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.76
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	3.19
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.56
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.	2.61
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	0.76
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.25
Solubility	0.0962 mg/ml ; 0.000561 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.	-3.82
Solubility	0.0258 mg/ml ; 0.00015 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	-2.78
Solubility	0.287 mg/ml ; 0.00167 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	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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.08 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	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)	1.73

Application In Synthesis of [ 16582-38-0 ]

* 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 [ 16582-38-0 ]

[ 16582-38-0 ] Synthesis Path-Downstream 1~35

1
[ 16582-38-0 ]
bis-(3-chloro-5-methyl-phenyl)-diazene [ No CAS ]

References: [1]Helvetica Chimica Acta,1944,vol. 27,p. 1080,1097.

2
[ 16582-38-0 ]
N,N'-bis-(3-chloro-5-methyl-phenyl)-hydrazine [ No CAS ]

References: [1]Helvetica Chimica Acta,1944,vol. 27,p. 1080,1097.

3
[ 16582-38-0 ]
[ 29027-20-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With tin(II) chloride dihdyrate; In ethanol; for 3.0h;Reflux;	3-Chloro-5-methyl-phenylamine. An ethanol solution (75 mL) containing <strong>[16582-38-0]1-chloro-3-methyl-5-nitro-benzene</strong> (5.0 g, 29 mmol) are added with SnCl2.2H2O (32.8 g, 146 mmol). The reaction mixture was reflux for 3.0 h. The solution was concentrated under vacuum, and the residue was re-dissolved in aqueous NaOH, filtered, and extracted with EtOAc. The organic layer was collected, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 3-chloro-5-methyl-phenylamine (4.0 g) as light yellow solids in 97% yield: 1H NMR (500 MHz, CDCl3) delta 6.56 (s, 1H), 6.48 (s, 1H), 6.36 (s, 1H), 3.66 (bs, 2H), 2.23 (s, 3H); ESI-MS: m/z 141.7 (M+H)+.
97%	With tin(II) chloride dihdyrate; ethanol; for 3.0h;Reflux;	An ethanol solution (75 mL) containing <strong>[16582-38-0]1-chloro-3-methyl-5-nitro-benzene</strong> (5.0 g, 29 mmol) were mixed with SnCl2.2H2O (32.8 g, 146 mmol). The reaction mixture was refluxed for 3.0 h. The solution was concentrated under vacuum, and the residue was re-dissolved in aqueous NaOH, filtered, and extracted with EtOA.c. The organic layer was collected, washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 3-chloro-5- methyl-phenylamine (4.0 g) as light yellow solids in 97% yield: 1H NMR (500 MHz, CDCl3) delta 6.56 (s, 1 H), 6.48 (s, 1 H), 6.36 (s, 1 ), 3.66 (s, 2 H), 2.23 (s, 3 H); ESI-MS: m/z 141.7 (M + H)+.
80%		3-Chloro-5-nitrotoluene (45 g, 0.241 mol) and ethanol (500 ml) were mixed in a 2 litter four-neck flask. The mixture was cooled to about 4 &deg C. A solution of tin chloride monohydrate (217.67 g, 0.965 mol) in 200 ml of ethanol was added dropwise to the mixture over 2 hours, while the reaction mixture was maintained at 10 &deg C. or lower. Then the reaction product mixture was stirred at room temperature for 2 hours and poured into 2500 ml of iced water. It was neutralized with sodium hydroxide and filtered with a nutsche filled with sellaite. The residue was washed with ethyl acetate. The intended product was obtained with ethyl acetate from the filtrate liquid. Then the extract liquid and the washing liquid were jointed. The mixture was washed with water and then a saturated salt water and dried with magnesium sulfate. Concentrated, it was treated by distillation at a reduced pressure to obtain 28.0 g of a yellow liquid (production yield 80%). B.p.: 85-92 &deg C./0.4 kPa or lower (3 Torr or lower) 1H-NMR, 500 MHz, in CDCl3 (delta) 6.56 (bs, 1H), 6.48 (dd, JI, J2=1.3 Hz, 1H), 6.36 (bs, 1H), 3.64 (bs, 2H), 2.22 (s, 3H)

80%		Example LII; 3-chloro-5-methyl-aniline; 2.4 g of <strong>[16582-38-0]3-chloro-5-nitro-toluene</strong> are dissolved in 35 ml of ethanol, combined with 15.8 g tin dichloride-dihydrate and refluxed for 3 hours. The solvent is eliminated in vacuo, the residue is taken up in 4 M sodium hydroxide solution and filtered through kieselguhr. The filter cake is washed thoroughly with ethyl acetate. The aqueous phase is extracted 3 times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution and dried on magnesium sulphate. The solvent is eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 81 :15 to 70:30). Yield: 1.59 g (80 % of theory) Mass spectrum (ESI+): m/z = 142 [M+H]+
		c. 3-Chloro-5-methylaniline Using a procedure similar to that described in Example 20a except starting with <strong>[16582-38-0]3-chloro-5-nitrotoluene</strong>, the title compound was obtained (85%)as a yellow solid; MS(CI): 142 (M+H). 300-MHz 1 H NMR (DMSO-d6): 6.56 (s, 1H), 6.48 (s, 1H), 6.36 (s, 1H), 3.65 (br s, 2H), 2.22 (s, 3H).
	With ethanol; tin(IV) chloride; at 85℃; for 2.0h;	To a solution of l-chloro-3-methyl-5 -nitrobenzene (1.61 g, 9.38 mmol) in EtOH (30 ml) was added tin chloride (8.90 g, 46.9 mmol). The reaction was heated at 85C for 2 h and was then quenched with INNaOH (50 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2x). The combined organic phase was washed with brine, dried over anhydrous MgS04, filtered and concentrated in vacuo. The residue was purified by chromatography on silica (Eluant: Hexane:EtOAc = 100:0 ~ 40:60) to afford the title compound 3-chloro-5-methylaniline. LCMS calc. = 142.03; found = 141.92 (M+H)+. 1H NMR (500 MHz, CDCI3): delta 6.56 (s, 1 H); 6.49 (s, 1 H); 6.37 (s, 1 H); 3.65 (brs, 2 H); 2.23 (s, 3 H).

References: [1]Patent: US2011/230486,2011,A1 .Location in patent: Page/Page column 31-32.
[2]Patent: WO2013/82324,2013,A1 .Location in patent: Paragraph 00358.
[3]Journal of Medicinal Chemistry,2000,vol. 43,p. 4726 - 4737.
[4]Patent: US2004/147776,2004,A1 .Location in patent: Page 2.
[5]Patent: WO2008/113760,2008,A2 .Location in patent: Page/Page column 137.
[6]Chemische Berichte,1887,vol. 20,p. 2419.
[7]Journal of the Chemical Society. Perkin transactions II,1980,p. 829 - 831.
[8]Chemische Berichte,1887,vol. 20,p. 2419.
[9]Patent: US5599814,1997,A .
[10],.
[11]Catalysis science and technology,2016,vol. 6,p. 4473 - 4477.
[12]Patent: WO2016/94260,2016,A1 .Location in patent: Page/Page column 41.

4
[ 69951-02-6 ]
[ 16582-38-0 ]

Yield	Reaction Conditions	Operation in experiment
90%		2-Chloro-4-nitro-6-methylaniline (55.0 g, 0.295 mol) and ethanol (500 ml) were mixed in a 2 litter four-neck flask. A conc. Sulfuric acid (120 ml) was added dropwise to the reaction mixture at a temperature being lower than room temperature. The reaction mixture was maintained at a temperature of 5 to 10 ° C. and an aqueous solution of sodium nitrite (26.44 g, 0.381 mol/40 ml) was added dropwise thereto over a period of 40 minutes. The reaction mixture was then stirred at room temperature. It was observed that the temperature elevated up to 45 ° C. by way of the reaction heat and then decreases down to lower than 40 ° C. and then the reaction mixture was stirred at a temperature of 40 to 45 ° C. until no foaming. The product mixture was cooled to room temperature and poured into 2500 ml of iced water to obtain precipitates. They were filtered and dried at a reduced pressure to obtain 45.95 g of a yellow solid (production yield 90%). 1H-NMR, 500 MHz, in CDCl3 (delta) 8.03 (bs, 1H), 7.94 (bs, 1H), 7.50 (bs, 1H), 2.46 (s, 3H)

References: [1]Patent: US2004/147776,2004,A1 .Location in patent: Page 2.
[2]Chemical news and journal of industrial science,1895,vol. 72,p. 58.
Chemisches Zentralblatt,1895,vol. 66,p. 530.
[3],.

5
[ 618-61-1 ]
[ 16582-38-0 ]

References: [1]Chemische Berichte,1887,vol. 20,p. 2419.
[2]Journal of the Chemical Society. Perkin transactions II,1980,p. 829 - 831.

6
[ 16582-38-0 ]
[ 22233-54-1 ]

References: [1]Bulletin de la Societe Chimique de France,1969,p. 624 - 628.

7
[ 16582-38-0 ]
C₇H₄Br₂ClNO₂ [ No CAS ]
1-(bromomethyl)-3-chloro-5-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	5-Chloro-3-nitrotoluene (synthesized following Journal ofMedicinal Chenaistry, 2000, 43, 4733) (0.33 g, 1.9 mmol) and NBS (0. 34 g, 1.9 mmol) were dissolved in 9 mL of CC14 and 10 mg of benzoylperoxide were added. The reaction was refluxed over night and the cooled to room temperature. The reaction mixture was filtered and the solvent evaporated after which the residue was dissolved in dichloromethane and was filtered through a plug of silica. The solvent was again evaporated to give 0.55 g crude product containing starting material the monobrominated and the dibrominated benzyl compound. Purification on silica (diethyl ether/heptane 9: 1) gave 0.13 g (27% yield) of 5-chloro-3-nitrobenzylbromide.
27%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Heating / reflux;	5-Chloro-3-nitrotoluene (synthesized following Journal of Medicinal Chemislry, 2000, 43, 4733) (0.33g, 1. 9 mmol) and NBS (0.34 g, 1.9 mmol) were dissolved in 9 mL of CC14 and 10 mg of benzoylperoxide were added. The reaction was refluxed over night and then cooled to room temperature. The reaction mixture was filtered and the solvent evaporated after which the residue was dissolved in dichloromethane and was filtered through a plug of silica. The solvent was again evaporated to give 0.55 g crude product containing starting material the monobrominated and the dibrominated benzyl compound. Purification on silica (diethylether/heptane 9 : 1) gave 0. 13 g (27% yield) of 5-chloro-3-nitrobenzylbromide.

References: [1]Patent: WO2005/92316,2005,A1 .Location in patent: Page/Page column 49.
[2]Patent: WO2005/92317,2005,A1 .Location in patent: Page/Page column 66.

10
[ 5465-33-8 ]
[ 16582-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium nitrite; In ethanol; water;	b. 3-Chloro-5-nitrotoluene To a stirred mixture of 2-chloro-4-methyl-6-nitroaniline (7.39 g, 39.7 mM) and concentrated sulfuric acid (6.2 mL) in absolute ethanol (50 mL) at 0-5 C. was slowly added a solution of sodium nitrite (6.85 g, 99.3 mM) in water (6 mL). The temperature of the reaction mixture was not allowed to exceed 5 C. during the addition. After the addition was completed, the reaction mixture was stirred at room temperature for 0.5 hr and then at reflux until the evolution of gas from the reaction mixture ceased. The reaction mixture was allowed to cool and was concentrated. The residue was slurried with ether and then filtered to remove the solids. The liltrate was concentrated and the residue chromatographed (eluant: diethyl ether/hexane; 1/9) to provide (6.25 g, 92%) the title compound as a yellow crystalline solid, mp 60.5-61 C.; MS(CI): 172 (M+H). Analysis for C7 H6 ClNO2 Calculated: C, 49.00; H, 3.52; N, 8.16 Found; C, 49.05; H, 3.53; N, 8.16

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4726 - 4737.
[2]Patent: US5599814,1997,A .

11
[ 16582-38-0 ]
[ 321853-32-1 ]