[ CAS No. 76439-45-7 ]

Name: 76439-45-7|3-Chloro-4-nitropyridine N-oxide|95%
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Product Details of [ 76439-45-7 ]

CAS No. :	76439-45-7	MDL No. :	MFCD00233948
Formula :	C₅H₃ClN₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MBHLTDWOVIYXEW-UHFFFAOYSA-N
M.W :	174.54 g/mol	Pubchem ID :	599817
Synonyms :

Calculated chemistry of [ 76439-45-7 ]

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 :	71.28 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.24
Log Po/w (XLOGP3) :	0.31
Log Po/w (WLOGP) :	0.88
Log Po/w (MLOGP) :	0.93
Log Po/w (SILICOS-IT) :	-1.35
Consensus Log Po/w :	0.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.46
Solubility :	6.12 mg/ml ; 0.0351 mol/l
Class :	Very soluble
Log S (Ali) :	-1.37
Solubility :	7.45 mg/ml ; 0.0427 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.62
Solubility :	41.7 mg/ml ; 0.239 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.09

Safety of [ 76439-45-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 76439-45-7 ]
Downstream synthetic route of [ 76439-45-7 ]

[ 76439-45-7 ] Synthesis Path-Upstream 1~6

1
[ 76439-45-7 ]
[ 19798-77-7 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1988, vol. 330, # 1, p. 154 - 158

2
[ 76439-45-7 ]
[ 52538-09-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 563 - 566

3
[ 1851-22-5 ]
[ 76439-45-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, 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

4
[ 626-60-8 ]
[ 1066-33-7 ]
[ 76439-45-7 ]

Reference： [1] Patent: US2003/69257, 2003, A1,

5
[ 626-60-8 ]
[ 1851-22-5 ]
[ 76439-45-7 ]

Reference： [1] Patent: US2003/69257, 2003, A1,

6
[ 626-60-8 ]
[ 76439-45-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 785 - 791
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 989 - 992

[ 76439-45-7 ] Synthesis Path-Downstream 1~46

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

Reference： [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)

Reference： [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 ]

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

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

Reference： [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 ]

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

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

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

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

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

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

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

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

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

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

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 662 - 665

14
[ 76439-45-7 ]
[ 109-76-2 ]
[ 944538-60-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

15
[ 76439-45-7 ]
[ 753483-42-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

16
[ 76439-45-7 ]
[ 753483-26-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

17
[ 76439-45-7 ]
[ 753483-25-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

18
[ 76439-45-7 ]
C₂₃H₂₆N₁₀O₅S₂*ClH [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

19
[ 76439-45-7 ]
C₄₁H₅₁N₁₀O₁₀S₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4211 - 4219

20
[ 76439-45-7 ]
2,6-diazaphenoxanthiine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 662 - 665

21
[ 76439-45-7 ]
[ 115857-55-1 ]

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

22
[ 76439-45-7 ]
[ 115855-41-9 ]

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

23
[ 76439-45-7 ]
[ 51520-77-5 ]

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

24
[ 76439-45-7 ]
[ 106835-13-6 ]

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

25
[ 76439-45-7 ]
[ 110919-67-0 ]

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

26
[ 76439-45-7 ]
[ 1796-73-2 ]

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

27
[ 76439-45-7 ]
[ 7322-04-5 ]

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

28
[ 76439-45-7 ]
[ 52538-09-7 ]

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

29
[ 76439-45-7 ]
[ 75-04-7 ]
[ 14043-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; acetonitrile; at 0 - 20℃;	2. Preparation of 3-Ethylamino-4-nitro-pyridine-1-oxide [0215] Anhydrous K2CO3 (19 g, 144.5 mmol) is suspended in a solution of <strong>[76439-45-7]3-chloro-4-nitro-pyridine-1-oxide</strong> (10 g, 57.8 mmol) in anhydrous acetonitrle (100 mL). Excess diethyl amine (2.0 M) in THF is added to the above suspension with ice-bath cooling. After complete addition of ethylamine, the reaction mixture is allowed to warm to room temperature and stir overnight. The reaction mixture is filtered to remove K2CO3 and the filtrate is evaporated under reduced pressure to remove volatile solvents. The organic residue is subjected to chromatography eluting with 30% EtOAc-hexanes to afford 3-ethylamino-4-nitro-pyridine-1-oxide as an orange solid (8.2 g) ; 1H NMR (300 MHz, CDCl3): 6 8.0 1 (d, J=7.5 Hz, 1H), 7.91(s, 1H), 7.8 (brs, NH), 7.44 (d, J=7.2 Hz, 1H) , 3.30 (t, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), m/z 184 [M+1]

Reference： [1]Patent: US2004/14780,2004,A1 .Location in patent: Page 18

30
[ 626-60-8 ]
[ 1066-33-7 ]
[ 76439-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; nitric acid; In sulfuric acid; water; acetic anhydride;	1. Preparation of 3-Chloro-4-nitropyridine N-oxide Aqueous hydrogen peroxide (30 mL of 30%) is added dropwise to an ice cold mixture of 3-chloropyridine (6.0 g, 53 mmol) in acetic anhydride (30 mL). The mixture is allowed to stir at ambient temperature for 24 h, water is then added and the mixture concentrated. The residue is taken up in concentrated sulfuric acid (10 mL) and fuming sulfuric acid (5 mL), and then cooled to 0 C. Concentrated nitric acid (24 mL) is added slowly, and the ice bath removed. The reaction is then heated at reflux for 2 h, icooled, and poured into ice water. Ammonium bicarbonate is added carefully until pH 8 is achieved, the solution is then extracted with dichloromethane. The organic layer is washed with water, dried (NaSO4), and concentrated to give 3-Chloro-4-nitropyridine N-oxide as a yellow solid. 1H NMR (CDCl3): delta 8.47 (d, J=4 Hz, H), 8.35 (dd, J=5, 12 Hz, 1H), 7.73 (ddd, J=4, 9, 12 Hz, 1H).

Reference： [1]Patent: US2003/69257,2003,A1

31
[ 626-60-8 ]
[ 1851-22-5 ]
[ 76439-45-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; nitric acid; In sulfuric acid; acetic anhydride;	1. Preparation of 3-Chloro-4-nitro-pyridine-1-oxide Aqueous 30% H2O2 (60 mL) is 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 up to room temperature slowly and then stirred overnight at room temperature. The reaction mixture is quenched with water (50 mL), diluted with toluene and concentrated to obtain the crude N-oxide as an oil in near quantitative yield. Fuming H2SO4 (25 mL) is added dropwise to a solution of crude 3-chloro-pyridine-1-oxide in concentrated H2SO4 (25 mL) under cold conditions (0 C.) with 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 to room temperature slowly. The resulting mixture is then heated at 120 C. for 4 h with stirring, cooled, 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. 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)

Reference： [1]Patent: US2003/69257,2003,A1

32
[ 76439-45-7 ]
[ 75-04-7 ]
3-ethylamino-4-nitro-3-pyridine N-oxide [ No CAS ]
[ 61719-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; ethanol;	2. Preparation of 3-Ethylamino-4-nitro-3-pyridine N-oxide To an ice cold solution of <strong>[76439-45-7]3-chloro-4-nitropyridine N-oxide</strong> (2.93 g, 16.8 mmol) in ethanol (30 mL) ethylamine (25 mL of 2M in THF) is added. The mixture is allowed to stir overnight at ambient temperature, then concentrated in vacuo to afford crude 3-Ethylamino-4-nitro-3-pyridine N-oxide as a yellow oil. 1H NMR (CDCl3): delta 8.01 (d, J=7 Hz, H), 7.91 (s, 1H), 7.45 (d, J=7 Hz, 1H), 3.31 (q, J=7 Hz, 2H), 1.40 (t, J=7 Hz, 3H) 3. Preparation of 3-Ethylamino-4-aminopyridine

Reference： [1]Patent: US2003/69257,2003,A1

33
N-{4-[4-(4-Aminopyrid-2-yl)piperazin-1-yl]phenyl}methanesulphonamide [ No CAS ]
[ 76439-45-7 ]
[ 112940-54-2 ]
[ 112940-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In water; butan-1-ol;	(i) N-{4-[4-(4-Nitro-1-oxidopyrid-3-yl)piperazin-1-yl]phenyl}methanesulphonamide A mixture of N-[(4-piperazin-1-yl)phenyl]methanesulphonamide hydrochloride (the product of Example 11, (iii) (0.59 g), <strong>[76439-45-7]3-chloro-4-nitropyridine-N-oxide</strong> (0.35 g) and sodium bicarbonate (0.50 g) in n-butanol (25 ml) was heated at 100 C. with stirring for 1.5 hours and then evaporated. The residue was stirred with water, filtered, and the solid was crystallized from methanol to give the title compound (0.55 g), m.p. 206-208 C. Found: C,48.77; H,4.91; N,17.52. C16 H19 N5 O5 S requires: C,48.84; H,4.87; N,17.80%.

Reference： [1]Patent: US4788196,1988,A

34
[ 110-85-0 ]
[ 76439-45-7 ]
[ 113049-46-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In butan-1-ol;	(i) 4-Nitro-3-(1-piperazinyl)pyridine-N-oxide STR54 A mixture of <strong>[76439-45-7]3-chloro-4-nitropyridine-N-oxide</strong> (3.00 g), piperazine (6.00 g) and potassium carbonate (3.00 g) in n-butanol (50 ml) was heated under reflux with stirring for 2 hours and then evaporated. The residue was partitioned between dichloromethane and 10% sodium carbonate solution. The aqueous layer was extracted several times with dichloromethane and the combined organic layers were dried (Na2 SO4) and evaporated to give the title compound, (3.0 g), pure enough for further reaction. A sample crystallized from ethanol/ethyl acetate had m.p. 167-169 C. Analysis %: Found: C, 48.36; H, 5.51; N, 24.77; C9 H12 N4 O3 requires: C, 48.21; H, 5.40; N, 24.99.

Reference： [1]Patent: US4806536,1989,A

35
[ 76439-45-7 ]
[ 904733-74-0 ]
[ 927205-43-4 ]

Reference： [1]Patent: WO2007/20877,2007,A1 .Location in patent: Page/Page column 33-34

36
[ 76439-45-7 ]
3-chloro-4-isopropoxypyridine-2-carbonitrile [ No CAS ]