61019-03-2|5-Methoxy-1,3-dimethyl-2-nitrobenzene| Ambeed

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Quality Control of [ 61019-03-2 ] Purity: 97% SDS Specification

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Product Details of [ 61019-03-2 ]

CAS No. :	61019-03-2
Formula :	C₉H₁₁NO₃
M.W :	181.19
SMILES Code :	O=[N+](C1=C(C)C=C(OC)C=C1C)[O-]
MDL No. :	MFCD00506726
InChI Key :	IGRJLJWPPSJVTG-UHFFFAOYSA-N
Pubchem ID :	143760

Safety of [ 61019-03-2 ]

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

Computational Chemistry of [ 61019-03-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	51.69
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.99
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	2.45
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.22
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.	2.07
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	0.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.72
Solubility	0.348 mg/ml ; 0.00192 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.	-3.25
Solubility	0.102 mg/ml ; 0.000563 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	-2.68
Solubility	0.379 mg/ml ; 0.00209 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.	-5.67 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)	1.61

Application In Synthesis of [ 61019-03-2 ]

* 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 [ 61019-03-2 ]

[ 61019-03-2 ] Synthesis Path-Downstream 1~25

1
[ 75-52-5 ]
2,6-dimethyl-4-methoxypyrylium perchlorate [ No CAS ]
[ 61019-03-2 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 565 - 583.
[2]Bulletin of the Chemical Society of Japan,1959,vol. 32,p. 707,709.

2
[ 61019-03-2 ]
[ 34743-49-2 ]

Yield	Reaction Conditions	Operation in experiment
78%		To a solution of intermediate 34 (1.81 g, 10 mmoles) in ethanol (20 ml) was added tin (II) chloride dihydrate (11.51 g, 50 mmoles) and the mixture was refluxed overnight. Upon cooling, ice was added to the reaction mixture followed by basification with 2N NaOH. The mixture was filtered and the filtrate was concentrated under reduced pressure. The aqueous solution was extracted with dichloromethane (4 x 30 ml). The organic layers were combined and dried over anhydrous MGSO4 and the solvent was removed under reduced pressure. The residue was purified on a silica gel column chromatography (CH2CL2 as eluent). Yield: 1.18 g of intermediate 35 (78%).
78%	With tin(ll) chloride; In ethanol;Heating / reflux;	b) Preparation of intermediate 6; To a solution of intermediate 5 (1.81g, 10 mmoles) in ethanol (20 ml) was added tin (II) chloride dihydrate (11.51g, 50 mmoles) and the mixture was refluxed overnight. Upon cooling, ice was added to the reaction mixture followed by basification with 2N NaOH. The mixture was filtered and the filtrate was concentrated under reduced pressure. The aqueous solution was extracted with dichloromethane (4 x 30 ml). The organic layers were combined and dried over anhydrous MgSCu and the solvent was removed under reduced pressure. The residue was purified on a silica gel columnchromatography (CH2C12 as eluent). Yield : 1.18 g (78%) of intermediate 6 (CI-MS : 152 [M+H]+).

References: [1]Patent: WO2004/74266,2004,A1 .Location in patent: Page 54-55.
[2]Patent: WO2006/15985,2006,A1 .Location in patent: Page/Page column 55-56.
[3]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1062 - 1080.
[4]Recueil des Travaux Chimiques des Pays-Bas,1958,vol. 77,p. 746,747.
[5]Journal of Medicinal Chemistry,1990,vol. 33,p. 854 - 861.

3
[ 19447-00-8 ]
[ 61019-03-2 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862.

4
[ 61019-03-2 ]
[ 64-19-7 ]
[ 94521-98-9 ]

References: [1]Bulletin of the Chemical Society of Japan,1959,vol. 32,p. 707,709.

5
[ 5344-97-8 ]
[ 77-78-1 ]
[ 61019-03-2 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1958,vol. 77,p. 746,747.

6
[ 75-52-5 ]
2,6-dimethyl-4-methoxypyrylium perchlorate [ No CAS ]
[ 865-48-5 ]
[ 75-65-0 ]
[ 61019-03-2 ]

References: [1]Bulletin of the Chemical Society of Japan,1959,vol. 32,p. 707,709.

7
[ 5344-97-8 ]
[ 74-88-4 ]
[ 61019-03-2 ]

References: [1]Journal of the Society of Chemical Industry,1930,vol. 49,p. 469 T, 472 T.

8
[ 874-63-5 ]
[ 18102-38-0 ]
[ 61019-03-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1981,p. 94 - 99.
[2]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1062 - 1080.

10
[ 19447-00-8 ]
[ 7697-37-2 ]
[ 61019-03-2 ]
4-methoxy-2,6-dimethyl-3-nitro-benzoic acid [ No CAS ]
[ 857590-05-7 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862.

11
[ 61019-03-2 ]
N,N'-bis-(4-methoxy-2,6-dimethyl-phenyl)-isophthalamide [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1062 - 1080.

12
[ 61019-03-2 ]
2,6-difluoro-N-(4-methoxy-2,6-dimethylphenyl)benzamide [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1062 - 1080.

13
[ 108-68-9 ]
[ 61019-03-2 ]

References: [1]Journal of the Society of Chemical Industry,1930,vol. 49,p. 469 T, 472 T.
[2]Journal of the American Chemical Society,1946,vol. 68,p. 1862.

14
[ 61019-03-2 ]
[ 391201-51-7 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1958,vol. 77,p. 746,747.

15
[ 70547-87-4 ]
[ 61019-03-2 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1862.

16
[ 874-63-5 ]
[ 61019-03-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	With sulfuric acid; nitric acid; In acetic acid; at 70.0℃; for 0.25h;	L-METHOXY-3, 5-DIMETHYLBENZENE (4.12 g, 30 mmoles) was dissolved in acetic acid (20 ml). To this solution was added dropwise a mixture of nitric acid (1.26 ml, 30 mmoles) and concentrated sulfuric acid (1.9 ML, 35 mmoles). The mixture was heated at 70 C for 15 minutes. After cooling, water was added and the mixture was extracted with dichloromethane. The organic extract was dry and evaporated. The resulting residue was purified by column chromatography (30% heptane in CH2CI2). Yield: 1.91 g of intermediate 34 (35%).
35%	With sulfuric acid; nitric acid; In acetic acid; at 70.0℃; for 0.25h;	Example A3; a) Preparation of intermediate 5; l-methoxy-3,5-dimethylbenzene (4.12g, 30 mmoles) was dissolved in acetic acid (20 ml). To this solution was added dropwise a mixture of nitric acid fuming (1.26 ml, 30 mmoles) and concentrated sulfuric acid (1.9 ml, 35 mmoles). The mixture was heated at 70 C for 15 minutes. After cooling, water was added and the mixture was extracted with dichloromethane. The organic extract was dried and evaporated. The resulting residue was purified by column chromatography (30% heptane in CH2CI2). Yield : 1.91g (35%) of intermediate 5 (CI-MS : 182 [M+H]+).

References: [1]Patent: WO2004/74266,2004,A1 .Location in patent: Page 54.
[2]Patent: WO2006/15985,2006,A1 .Location in patent: Page/Page column 55.
[3]Chemistry - A European Journal,2018,vol. 24,p. 7671 - 7682.

17
[ 5344-97-8 ]
[ 584-08-7 ]
[ 80-48-8 ]
[ 61019-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; acetone;	Step I 3,5-dimethyl-4-nitroanisole 3,5-dimethyl-4-nitrophenol (33.43 g), methyl p-toluene sulfonate (40.97 g) and K2 CO3 (31.79 g) are stirred at reflux in 200 ml of acetone for four and one half hours and then stirred at R.T. overnight. The reaction mixture is filtered to give a dark amber filtrate. The filtrate is concentrated in vacuo to a yellowish brown solid which is dissolved in ethyl acetate washed with saturated aqueous sodium chloride, dried and concentrated in vacuo. The concentrate is distilled (87-104 C./0.10 mm) to give a yellow waxy looking solid. The solid is dissolved in hot ethanol and recrystallized, M.P. 50-52 C.

References: [1]Patent: US4564640,1986,A .

18
[ 1336-21-6 ]
[ 60-29-7 ]
[ 61019-03-2 ]
[ 102440-03-9 ]
[ 142-04-1 ]