109466-84-4|2-Amino-4-nitrobenzaldehyde| Ambeed

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Quality Control of [ 109466-84-4 ] Purity: 95% SDS Specification

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Product Details of [ 109466-84-4 ]

CAS No. :	109466-84-4
Formula :	C₇H₆N₂O₃
M.W :	166.13
SMILES Code :	O=CC1=CC=C([N+]([O-])=O)C=C1N
MDL No. :	MFCD09264065
InChI Key :	DKVANZONLCMNBC-UHFFFAOYSA-N
Pubchem ID :	13891180

Safety of [ 109466-84-4 ]

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

Computational Chemistry of [ 109466-84-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	45.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	88.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.55
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	1.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.0
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.	-0.31
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	-0.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.1
Solubility	1.33 mg/ml ; 0.008 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.	-3.05
Solubility	0.149 mg/ml ; 0.000896 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	-1.36
Solubility	7.25 mg/ml ; 0.0437 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	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	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.	-6.2 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	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<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)	1.77

Application In Synthesis of [ 109466-84-4 ]

* 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.

Upstream synthesis route of [ 109466-84-4 ]
Downstream synthetic route of [ 109466-84-4 ]

[ 109466-84-4 ] Synthesis Path-Upstream 1~6

1
[ 78468-34-5 ]
[ 109466-84-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With manganese(IV) oxide In dichloromethane at 20℃; for 23 h; Inert atmosphere	5.1.133 6,7-Didehydro-17-methyl-7'-nitroquinolino[2',3':6,7]morphinan-3,14β-diol hydrochloride (SYK-71) SYK-71 was prepared from compound 29c according to the procedure used to prepare SYK-27. Yield, 98percent; a yellow amorphous solid. Mp 247-249 °C (dec). Anal. Calcd for C₂₄H₂₃N₃O₄·1.0HCl·1.2H₂O: C, 60.62; H, 5.60; N, 8.84. Found: C, 60.69; H, 5.61; N, 8.85.
86%	With manganese(IV) oxide In tetrahydrofuran; dichloromethane at 20℃; for 2 h;	A mixture of(2-amino-4-nitrophenyl)methanol (650 mg, 3.87 mmol) and manganese dioxide (1680 mg, 19.33 mmol) in THF (5 mL) and dichloromethane (25 mL) was stirred at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (40percent —* 50percent ethyl acetate in hexanes; 25g column) to afford 2-amino-4-nitrobenzaldehyde (550 mg, 86percent yield) as an orange solid: ‘H NMR (400MHz, DMSO-d6) ö 9.99 (s, 1H), 7.85 (d, J=8.6 Hz, 1H), 7.63 (d, J=2.3 Hz, 1H), 7.55 (br. s., 2H), 7.35 (dd, J=8.6, 2.3 Hz, 1H).

References: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831.
[2] Patent: WO2015/6100, 2015, A1, . Location in patent: Page/Page column 113.
[3] Patent: EP2128157, 2009, A1, . Location in patent: Page/Page column 103.
[4] Patent: WO2015/95795, 2015, A1, . Location in patent: Paragraph 0586.

2
[ 528-75-6 ]
[ 109466-84-4 ]

Yield	Reaction Conditions	Operation in experiment
98 %Chromat.	With hydrogen In methanol at 100℃; for 6 h; Autoclave	General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15molpercent Co/C–N–X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC–MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

References: [1] Chemische Berichte, 1904, vol. 37, p. 1873.
[2] Recueil des Travaux Chimiques des Pays-Bas, 1920, vol. 39, p. 581.
[3] Journal of Molecular Catalysis A: Chemical, 2016, vol. 420, p. 56 - 65.

3
[ 619-17-0 ]
[ 109466-84-4 ]

References: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831.
[2] Patent: WO2015/6100, 2015, A1, .
[3] Patent: WO2015/95795, 2015, A1, .

4
[ 52785-71-4 ]
[ 109466-84-4 ]

References: [1] Journal of Photochemistry and Photobiology A: Chemistry, 2010, vol. 214, # 2-3, p. 188 - 193.

5
[ 121-14-2 ]
[ 71-43-2 ]
[ 92-52-4 ]
[ 109466-84-4 ]
[ 99-09-2 ]
[ 619-17-0 ]

References: [1] Journal of Organic Chemistry, 1991, vol. 56, # 10, p. 3306 - 3314.

6
[ 61599-67-5 ]
[ 71-43-2 ]
[ 121-14-2 ]
[ 109466-84-4 ]

References: [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1086,1094.

[ 109466-84-4 ] Synthesis Path-Downstream 1~37

1
[ 108-86-1 ]
[ 109466-84-4 ]
2-anilino-4-nitro-benzaldehyde [ No CAS ]

References: [1]Chemische Berichte,1938,vol. 71,p. 808,813.

2
[ 528-75-6 ]
[ 109466-84-4 ]

Yield	Reaction Conditions	Operation in experiment
98%Chromat.	With hydrogen; In methanol; at 100.0℃; under 7500.75 Torr; for 6.0h;Autoclave;	General procedure: The hydrogenation of nitroarenes was carried out in a Teflon-lined stainless steel autoclave equipped with a pressure gauge anda magnetic stirrer. Typically, a mixture of 0.5 mmol nitroarene, 15mol% Co/C-N-X catalyst, 100 L n-hexadecane and 2 mL solventwas introduced into the reactor at room temperature. Air in theautoclave was purged several times with H2. Then, the reactionbegan by starting the agitation (600 r/min) when hydrogen was reg-ulated to 1 MPa after the reaction temperature was reached. Afterreaction, the solid was isolated from the solution by centrifuga-tion. The products in the solution were quantified and identifiedby GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a0.25 mm × 30 m DB-WAX capillary column).1H NMR and13C NMRdata were obtained on Bruker Avance III 400 spectrometer usingCDCl3or DMSO-d6 as solvent and tetrmethylsilane (TMS) as aninternal standard. The pure product in the scale-up experimentwas obtained by flash column chromatography (petroleum ether and ethyl acetate).

References: [1]Chemische Berichte,1904,vol. 37,p. 1873.
[2]Recueil des Travaux Chimiques des Pays-Bas,1920,vol. 39,p. 581.
[3]Journal of Molecular Catalysis A: Chemical,2016,vol. 420,p. 56 - 65.

3
[ 109466-84-4 ]
[ 102978-40-5 ]
[ 109581-96-6 ]