76439-45-7|3-Chloro-4-nitropyridine N-oxide| Ambeed

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Quality Control of [ 76439-45-7 ] Purity: 95% SDS Specification

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Product Details of [ 76439-45-7 ]

CAS No. :	76439-45-7
Formula :	C₅H₃ClN₂O₃
M.W :	174.54
SMILES Code :	O=[N+](C1=CC=[N+]([O-])C=C1Cl)[O-]
MDL No. :	MFCD00233948
Boiling Point :	No data available
InChI Key :	MBHLTDWOVIYXEW-UHFFFAOYSA-N
Pubchem ID :	599817

Safety of [ 76439-45-7 ]

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

Computational Chemistry of [ 76439-45-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	41.44
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.28 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.24
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	0.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.88
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.	0.93
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	-1.35
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.46
Solubility	6.12 mg/ml ; 0.0351 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.37
Solubility	7.45 mg/ml ; 0.0427 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.62
Solubility	41.7 mg/ml ; 0.239 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.	-7.14 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)	2.09

Application In Synthesis of [ 76439-45-7 ]

* 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 [ 76439-45-7 ]

[ 76439-45-7 ] Synthesis Path-Downstream 1~35

1
[ 626-60-8 ]
[ 76439-45-7 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 785 - 791.
[2]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 989 - 992.

2
[ 1851-22-5 ]
[ 76439-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid; In sulfuric acid;	EXAMPLE 141B 4-nitro-3-chloropyridine-N-oxide Example 141B was processed as in Caldwell and Martin (J. Heterocyclic Chem., 1980, 17, 989). Example 141A (16.8 g, 130 mmol) in sulfuric acid (25 mL, 98%), fuming sulfuric acid (30% SO3, 10 mL), and nitric acid (60 mL, 90%) was heated at 120 C. for 2 hours, cooled to room temperature, poured into ice water (200 mL), solid ammonium carbonate was added to bring the solution to pH=9, and extracted with methylene chloride (4*100 mL). The extracts were dried (Na2SO4) and concentrated. The residue was recrystallized from ethyl acetate-hexanes to provide a clean first crop of the title compound. Second crop recrystallizations provided mixtures of title compound and side products. MS (DCI/NH3) m/z 194 (37Cl)/192 (35Cl), (M+NH4)+; 177 (37Cl)/175 (35Cl), (M+H)+; 1H NMR (CDCl3, 300 MHz) delta 8.01 (d, 1H), 8.14 (dd, 1H), 8.32 (d, 1H).
	With sulfuric acid; nitric acid; at 0 - 120℃; for 4h;	Example 10 3-ETHYL-2- [2-(3-FLUORO-PHENYL)-IMIDAZOL-1-YLMETHYL] -3H-IMIDAZO[4,5-C] PYRIDINE [0212] [CHEMMOL-00024] 1. Preparation of 3-Chloro-4-nitro-pyridine-1-oxide [0213] Aqueous 30% H2O2 (60 mL) was added dropwise to a magnetically stirred solution of 3-chloro-pyridine (12 g, 105 mmol) in acetic anhydride (60 mL) under cold conditions (0 to 10 C.). The resulting mixture is allowed to warm to room temperature slowly and stirred overnight. The reaction mixture is quenched with water (50 mL), diluted with toluene and concentrated to obtain crude N-oxide as an oil that is used without further purification. [0214] Fuming H2SO4 (25 mL) is added dropwise to a solution of crude 3-chloro-pyridine-1-oxide in concentrated H2SO4 (25 mL) with cooling (0 C.) and stirring. HNO3 (fuming, 90%, 60 mL) is added carefully to the above mixture with caution to keep the offset of any exotherm under control, and then allowed to warm up to room temperature slowly. The resulting mixture is then heated at 120 C. for 4 hours with stirring, cooled, and poured into ice-cold water, and extracted with CHCl3. The combined organic phase is washed successively with saturated aqueous NaHCO3, water, brine, dried over Na2SO4, and concentrated in vacuo to afford 3-chloro-4-nitro-pyridine-1-oxide as an yellow solid (10 g) ; 1H NMR (300 MHz, CDCl3): 1H NMR (300 MHz, CDCl3): delta 8.31 (d, J=1.5 Hz, 1H) , 8.13 (dd, J=1.5, 5.4 Hz, 1H) 7.95 (d, J=7.2 Hz, 1H)

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 989 - 992.
[2]Patent: US6232320,2001,B1 .
[3]Patent: WO2007/20877,2007,A1 .Location in patent: Page/Page column 33.
[4]Patent: US2004/14780,2004,A1 .Location in patent: Page 18.

3
[ 23003-22-7 ]
[ 76439-45-7 ]
[ 110919-66-9 ]
[ 110919-65-8 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 211 - 213.
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 211 - 213.

4
[ 76439-45-7 ]
[ 69212-29-9 ]
[ 113372-48-8 ]
[ 113372-47-7 ]

References: [1]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1357 - 1362.

5
[ 76439-45-7 ]
[ 496-74-2 ]
[ 106835-15-8 ]
[ 106835-14-7 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 785 - 791.
[2]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 785 - 791.

6
[ 76439-45-7 ]
[ 35180-64-4 ]
[ 76451-84-8 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 989 - 992.

7
[ 76439-45-7 ]
[ 109681-74-5 ]
[ 115855-40-8 ]
[ 115855-39-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2839 - 2844.

8
[ 76439-45-7 ]
[ 19798-77-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1988,vol. 330,p. 154 - 158.

9
[ 76439-45-7 ]
[ 17534-15-5 ]
[ 106835-12-5 ]

References: [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 785 - 791.

10
[ 76439-45-7 ]
[ 74-89-5 ]
[ 1796-82-3 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 563 - 566.

11
[ 76439-45-7 ]
[ 173278-51-8 ]
[ 173278-52-9 ]