38469-84-0|5-Methoxy-2-nitrobenzonitrile| Ambeed

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Quality Control of [ 38469-84-0 ] Purity: 95% SDS Specification

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Product Details of [ 38469-84-0 ]

CAS No. :	38469-84-0
Formula :	C₈H₆N₂O₃
M.W :	178.15
SMILES Code :	C1=CC(=C(C#N)C=C1OC)[N+]([O-])=O
MDL No. :	MFCD09056823
InChI Key :	GCXTYFJQZDWUNU-UHFFFAOYSA-N
Pubchem ID :	319474

Safety of [ 38469-84-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332
Precautionary Statements:	P280

Computational Chemistry of [ 38469-84-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	46.47
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.2
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	1.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.48
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.	0.03
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	-0.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.23
Solubility	1.05 mg/ml ; 0.00587 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.	-2.98
Solubility	0.186 mg/ml ; 0.00104 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	-1.99
Solubility	1.82 mg/ml ; 0.0102 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	No
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.	-6.17 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)	1.81

Application In Synthesis of [ 38469-84-0 ]

* 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 [ 38469-84-0 ]

[ 38469-84-0 ] Synthesis Path-Downstream 1~18

1
[ 38469-84-0 ]
[ 1882-71-9 ]

References: [1]Bulletin de la Societe Chimique de France,1972,p. 2365,2372.

2
[ 38469-84-0 ]
[ 23842-82-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen;palladium 10% on activated carbon; In methanol; ethyl acetate; at 20℃; under 1292.9 Torr; for 0.333333h;	Step 2: A solution of the nitro compound from Step 1 (6.5 g, 36 mmol) in 4:1 EtOAc: MeOH (150 ml_) in a pressure vessel was degassed with by bubbling N2 through the solution for 10 min. To this solution was added 10% Pd/C (300 mg). The vessel was sealed and pressurized with H2 to 25 psi. The vessel was then shaken at RT for 20 min. Once the reaction was complete, the vessel was purged with N2. The mixture was filtered through Celite and concentrated. The crude product was purified via flash chromatography (SiO2: gradient elution, 100:0 to 60:40 hexanes: EtOAc) to afford the aniline (6.4 g, 100%) as a light yellow solid.
84%	With sodiumsulfide nonahydrate; acetic acid; In N,N-dimethyl-formamide; at 20℃; for 20h;Green chemistry;	General procedure: Condition B: An oven-dried pressure tube (10 mL) was charged with sodium sulfide nonahydrate (144 mg, 0.6 mmol), acetic acid (36 mg, 0.6 mmol), nitrobenzene (24.6 mg, 0.2 mmol), DMF (0.8 mL). The reaction vessel was closed under air and the resulting solution was stirred at room temperature for 20 h. Then the reaction mixture was filtered through a pad of silica gel and washed with 5 mL ethyl acetate for three times. The filtrate was removed under vacuum and the residue was purified by flash column chromatography (silica gel, petroleum ether/ethyl acetate = 4:1) to give the desired product.
	With sodium dithionite; water; In ethanol; for 1h;Reflux;	Step 3 2-Amino-5-methoxybenzonitrile A 100 mL round bottom flask was charged with <strong>[38469-84-0]5-methoxy-2-nitrobenzonitrile</strong> (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.

With sodium dithionite; water; In ethanol; for 1h;Reflux;

2-Amino-5-methoxybenzonitrile: [0441] A 100 mL round bottom flask was charged with 5-methoxy-2- nitrobenzonitrile (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2S04 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.

References: [1]Patent: WO2009/5646,2009,A2 .Location in patent: Page/Page column 186.
[2]Tetrahedron Letters,1984,vol. 25,p. 839 - 842.
[3]Organic Preparations and Procedures International,2009,vol. 41,p. 423 - 427.
[4]Chemical Papers,2019,vol. 73,p. 965 - 975.
[5]Chemistry - A European Journal,2004,vol. 10,p. 2487 - 2506.
[6]Australian Journal of Chemistry,1972,vol. 25,p. 2621 - 2629.
[7]Patent: US2010/120741,2010,A1 .Location in patent: Page/Page column 59.
[8]Patent: WO2011/112731,2011,A2 .Location in patent: Page/Page column 144.

3
[ 20357-24-8 ]
[ 38469-84-0 ]

References: [1]Organic Preparations and Procedures International,2009,vol. 41,p. 423 - 427.
[2]Chemistry - A European Journal,2004,vol. 10,p. 2487 - 2506.
[3]Australian Journal of Chemistry,1972,vol. 25,p. 2621 - 2629.

5
[ 42454-06-8 ]
[ 38469-84-0 ]