936247-35-7|5-Chloro-2-nitropyridin-3-ol| Ambeed

Structure of 936247-35-7

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Quality Control of [ 936247-35-7 ] Purity: 97% SDS Specification

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Product Details of [ 936247-35-7 ]

CAS No. :	936247-35-7
Formula :	C₅H₃ClN₂O₃
M.W :	174.54
SMILES Code :	OC1=CC(Cl)=CN=C1[N+]([O-])=O
MDL No. :	MFCD18259798
InChI Key :	XRSYKYYBXLVPAJ-UHFFFAOYSA-N
Pubchem ID :	18765698

Safety of [ 936247-35-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 936247-35-7 ] 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	4.0
Num. H-bond donors	1.0
Molar Refractivity	40.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.88
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	1.84
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.35
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.	0.12
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	-0.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.42
Solubility	0.665 mg/ml ; 0.00381 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.	-3.12
Solubility	0.133 mg/ml ; 0.000762 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	-1.44
Solubility	6.29 mg/ml ; 0.0361 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.	-6.06 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)	2.09

Application In Synthesis of [ 936247-35-7 ]

* 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 [ 936247-35-7 ]

[ 936247-35-7 ] Synthesis Path-Downstream 1~35

1
[ 936247-35-7 ]
[ 100-39-0 ]
[ 936247-05-1 ]

Yield	Reaction Conditions	Operation in experiment
91.0%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step A: Preparation of 3-fbenzyloxy)-5-chloro-2-mtropyridine:; l-(Bromomethyl)benzene (7.905 ml, 66.46 mmol) was added to a mixture of cesium carbonate (21.65 g, 66.46 mmol) and <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (11.6 g, 66.46 mmol) in DMF (50 mL). The reaction mixture was stirred overnight at ambient temperature, then partitioned between ethyl acetate and water, washed with water and brine, dried, and concentrated to afford 3-(benzyloxy)-5-chloro- 2-nitropyridine (16.0 g, 91.0% yield) as a light yellow powder. 1H NMR (CDCl3) delta 5.25 (s, 2H), 7.41 (m, 5H), 7.53 (s, IH), 8.04 (s, IH).

References: [1]Patent: WO2007/53345,2007,A1 .Location in patent: Page/Page column 150.

2
[ 936247-35-7 ]
[ 6482-24-2 ]
[ 1144110-06-4 ]

Yield	Reaction Conditions	Operation in experiment
60%		5-Chloro-2-nitro-pyridine-3-ol (1.15 mmol) is dissolved in DMF (2 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added and the suspension is stirred 45 min at room temperature. 1-Bromo-2-methoxy- ethane (1 eq.) is added and the reaction suspension is heated to 100 0C for 24 hours. The reaction solution is pored into water and extracted with dichloromethane. The combined organic layers are washed with brine, <n="62"/>dried over MgSO4 and the solvent is removed in vacuo. 5-Chloro-3-(2- methoxy-ethoxy)-2-nitro-pyridine is obtained after column chromatography as beige solid in a yield of 60 %; mp. 71.5-72.5; HPLC (method C): 1.63 min; LC-MS (method A): 1.36 min, 232.95 (M+H+).

References: [1]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 60-61.

3
[ 936247-35-7 ]
[ 3637-61-4 ]
[ 1144110-24-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃; for 5h;	5-Chloro-2-nitro-pyridine-3-ol (5.7 mmol) is dissolved in THF (35 ml) and triphenylphosphin (2 eq.) and cyclopentylmethanol (1 eq.) is added at 0 C. After addition of di-tert.-butylazodicarboxylate (1.5 eq) in THF (10 *5 ml), the reaction is stirred five hours at 0 0C. The solvent is removed in vacuo. delta-Chloro-S-cyclopentylmethoxy^-nitro-pyridine is obtained after column chromatography (heptane / ethylacetate) as yellow solid in a yield of 74 %. HPLC (method C): 2.23 min; LC-MS (method A): 2.27 min,0 257.05 (MH+).

References: [1]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 74.

4
[ 936247-35-7 ]
[ 107-98-2 ]
[ 1144110-19-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃; for 5h;	5-Chloro-3-pyridinol (382 mmol) is dissolved in concentrated H2SO4 (375 ml). At 5 0C concentrated nitric acid (25 ml) is added. The reaction is allowed to warm to room temperature over 3 hours. The reaction solution is pored onto ice water (5000 ml). The precipitate is filtered, washed with water and dried over night at 40 0C in vacuo. 5- Chloro-2-nitro-pyridine-3-ol is obtained as yellow powder in a yield of 74 %. Mp.: 97 0C; LC-MS (Method B): 1.35 min, 175.1 (MH+).

References: [1]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 72.

5
[ 936247-35-7 ]
[ 1556-18-9 ]
[ 1144110-10-0 ]

Yield	Reaction Conditions	Operation in experiment
60%		5-Chloro-2-nitro-pyridine-3-ol (3.4 mmol) is dissolved in DMF (2 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added and the <n="64"/>suspension is stirred 45 min at room temperature. Cyclopentyliodide (1 eq.) is added and the reaction suspension is heated to 100 0C for 24 hours. The reaction solution is pored into water and extracted with dichloromethane. The combined organic layers are washed with brine, 5 dried over MgSO4 and the solvent is removed in vacuo. 5-Chloro-3- cyclopentyloxy-2-nitro-pyridine is obtained after column chromatography as yellow oil in a yield of 60 %; HPLC (method C): 2.11 min; LC-MS (method A): 2.07 min, 243.10 (M+H+).

References: [1]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 62-63.

6
[ 936247-35-7 ]
[ 109-86-4 ]
[ 1144110-06-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 5h;	5-Chloro-2-nitro-pyridine-3-ol (86 mmol) is dissolved in THF (300 ml) and triphenylphosphin (2 eq.) and ethyleneglycolmonomethylether (1 eq.) is added at 0 0C. After addition of di-tert.-butylazodicarboxylate (2 eq) in THF (100 ml), the reaction is stirred five hours at room temperature. The solvent is removed in vacuo. 5-Chloro-3-(2-methoxy-ethoxy)-2-nitro- pyridine is obtained after column chromatography (heptane / ethyl acetate) as yellow solid in a yield of 90 %. HPLC (method C): 1.59 min; LC-MS (method A): 1.47 min, 233.1 (MH+).

References: [1]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 77.

7
[ 74115-12-1 ]
[ 936247-35-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sulfuric acid; nitric acid; at 20℃;	Example 15A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and, at 0 C., 24 ml of concentrated nitric acid were added slowly. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	Example 7A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and, at 0 C., 24 ml of concentrated nitric acid were added slowly. The reaction was warmed to RT and stirred overnight. The reaction mixture was stirred into an ice/water mixture and it was stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction. LC-MS (Method 2): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	Example 12A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and, at 0 C., 24 ml of concentrated nitric acid were added slowly. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound, which were used without further purification for the next reaction. LC-MS (Method 2): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).

82%	With sulfuric acid; nitric acid; at 0 - 20℃;	With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The mixture was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H), 8.10 (d, 1H), 12.14 (br. 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 00 C. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 mm. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction.10524] LC-MS (Method 1): R=0.60 mm10525] MS (ESneg): mlz=172.9/174.9 (M-H)10526] ?H-NMR (400 MHz, DMSO-d5): oe=7.71 (d, 1H);8.10 (d, 1H); 12.14 (bt 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 2): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulfuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 Mhz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
82%	With sulfuric acid; nitric acid; at 0 - 20℃;	With ice cooling, 30 g of 5-chloropyridin-3-ol (232mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for 30 mm. The crystals were filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without thrther purification for the next reaction.10372] LC-MS (Method 2): R=0.60 mm10373] MS (ESneg): mlz=172.9/174.9 (M-H)j0374] ?H-NMR (400 MHz, DMSO-d5): oe=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (bt 1H).
74%	With sulfuric acid; nitric acid; In water; at 5 - 20℃; for 3 - 144h;Product distribution / selectivity;	5-Chloro-3-pyridinol (15.3 mmol) is dissolved in concentrated H2SO4 (15 ml). At 5 0C concentrated nitric acid (0.9 ml) is added. The reaction mixture is allowed to warm to room temperature over 6 days. The reaction solution is pored onto ice (50 ml) and diluted with water (200 ml). The precipitate is filtered, washed with water and dried at 40 0C in vacuo. 5-Chloro-2-nitro-pyridine-3-ol is obtained as yellow powder; mp. 97; LC- MS (method B): 1.35 min, 175.1 (M+H+).; 5-Chloro-3-pyridinol (382 mmol) is dissolved in concentrated H2SO4 (375 ml). At 5 0C concentrated nitric acid (25 ml) is added. The reaction is allowed to warm to room temperature over 3 hours. The reaction solution is pored onto ice water (5000 ml). The precipitate is filtered, washed with water and dried over night at 40 0C in vacuo. 5- Chloro-2-nitro-pyridine-3-ol is obtained as yellow powder in a yield of 74 %. Mp.: 97 0C; LC-MS (Method B): 1.35 min, 175.1 (MH+).
67%	With sulfuric acid; nitric acid; at 5 - 20℃; for 3h;	5-chloropyridin-3-ol(2.00 g, 15.4 mmol) was dissolved in concentrated H2SO4(15 mL) at 5 C. Concentrated nitric acid (1.0 mL) was then added. The reactionwas allowed to warm to room temperature over 3 hrs. The reaction solution waspoured onto ice water (25 mL). The resultant precipitate was filtered, washedwith water and dried overnight at 40 C in vacuo to afford was obtained as ayellow powder, (1.80g, 67%); H NMR (400 MHz, CDCI3) delta7.68 (d, 1H), 8.15 (d, 1H), 10.29 (s, 1H).
	With sulfuric acid; nitric acid; at 0 - 20℃;Cooling with ice;	Example 27A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, I equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT and stirred overnight. The mixture was stirred into an ice/water mixture and stirred for 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method D): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
33 g	With sulfuric acid; nitric acid; at 0 - 20℃;	Example 7A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H)- 1H-NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).
	With nitric acid;	Example 7A 5-Chloro-2-nitropyridin-3-ol With ice cooling, 30 g of 5-chloropyridin-3-ol (232 mmol, 1 equivalent) were dissolved in 228 ml of concentrated sulphuric acid, and 24 ml of concentrated nitric acid were added slowly at 0 C. The reaction was warmed to RT, stirred overnight and then stirred into an ice/water mixture and stirred for another 30 min. The solid was filtered off, washed with cold water and air-dried. This gave 33 g (82% of theory) of the title compound which was used without further purification for the next reaction. LC-MS (Method 1): Rt=0.60 min MS (ESneg): m/z=172.9/174.9 (M-H) 1H-NMR (400 MHz, DMSO-d6): delta=7.71 (d, 1H); 8.10 (d, 1H); 12.14 (br. 1H).

References: [1]Patent: US2014/128386,2014,A1 .Location in patent: Paragraph 1052; 1053; 1054; 1056.
[2]Patent: US2014/128425,2014,A1 .Location in patent: Paragraph 0393-0397.
[3]Patent: US2014/128372,2014,A1 .Location in patent: Paragraph 0414; 0415; 0416; 0417; 0418.
[4]Patent: US2016/122341,2016,A1 .Location in patent: Paragraph 0545; 0546; 0547; 0548; 0549.
[5]Patent: US2016/347770,2016,A1 .Location in patent: Paragraph 0522; 0523; 0524; 0525; 0526.
[6]Patent: US2017/57958,2017,A1 .Location in patent: Paragraph 0197-0201.
[7]Patent: US2017/304278,2017,A1 .Location in patent: Paragraph 0696; 0697; 0698; 0699; 0700.
[8]Patent: US2016/362408,2016,A1 .Location in patent: Paragraph 0370; 0371; 0372; 0373; 374.
[9]Patent: WO2009/46784,2009,A1 .Location in patent: Page/Page column 60; 71.
[10]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 69.
[11]Patent: US2017/50961,2017,A1 .Location in patent: Paragraph 0929; 0930; 0931; 0932; 0933.
[12]Patent: US2017/57954,2017,A1 .Location in patent: Paragraph 0542; 0543; 0544l 0545; 0546.
[13]Patent: US2017/217954,2017,A1 .

8
[ 936247-35-7 ]
[ 85118-00-9 ]
[ 534-17-8 ]
[ 1609082-28-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 8A 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine 33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 7A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).

References: [1]Patent: US2017/217954,2017,A1 .

9
[ 936247-35-7 ]
[ 1609082-30-5 ]

References: [1]Patent: US2014/128386,2014,A1 .
[2]Patent: US2014/128425,2014,A1 .
[3]Patent: US2014/128372,2014,A1 .
[4]Patent: US2016/122341,2016,A1 .
[5]Patent: US2017/57954,2017,A1 .
[6]Patent: US2016/347770,2016,A1 .
[7]Patent: US2017/57958,2017,A1 .
[8]Patent: US2017/217954,2017,A1 .
[9]Patent: US2016/362408,2016,A1 .

10
[ 936247-35-7 ]
[ 1609082-31-6 ]

11
[ 936247-35-7 ]
[ 1609166-13-3 ]

References: [1]Patent: US2014/128386,2014,A1 .
[2]Patent: US2017/50961,2017,A1 .
[3]Patent: US2017/304278,2017,A1 .

12
[ 936247-35-7 ]
[ 1609166-14-4 ]

References: [1]Patent: US2014/128386,2014,A1 .
[2]Patent: US2017/50961,2017,A1 .
[3]Patent: US2017/304278,2017,A1 .

13
[ 936247-35-7 ]
[ 1609235-99-5 ]

References: [1]Patent: US2014/128386,2014,A1 .
[2]Patent: US2017/50961,2017,A1 .
[3]Patent: US2017/304278,2017,A1 .

14
[ 936247-35-7 ]
[ 1609082-29-2 ]

15
[ 936247-35-7 ]
[ 1609345-76-7 ]

References: [1]Patent: US2014/128372,2014,A1 .

16
[ 936247-35-7 ]
[ 1609348-37-9 ]

References: [1]Patent: US2014/128372,2014,A1 .

17
[ 936247-35-7 ]
[ 1609340-83-1 ]

References: [1]Patent: US2014/128372,2014,A1 .

18
[ 936247-35-7 ]
[ 1609341-14-1 ]

References: [1]Patent: US2014/128372,2014,A1 .

19
[ 936247-35-7 ]
N-[(3S)-3-aminobutan-2-yl]-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

References: [1]Patent: US2014/128372,2014,A1 .

20
[ 936247-35-7 ]
[ 149489-32-7 ]
[ 1609166-12-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃;	Example 126A 5-Chloro-3-[(3-fluoropyridin-2-yl)methoxy]-2-nitropyridine 20.0 g (114.6 mmol) of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong>e from Example 15A and 56.0 g (171.9 mmol) of caesium carbonate were initially charged in 319 ml of DMF. 17.51 g (120.3 mmol) of 2-(chloromethyl)-3-fluoropyridine (commercially available; additionally described in: K. Weidmann et al. Journal of Medicinal Chemistry 1992, 35, 438-450; U.S. Pat. No. 5,593,993, 1997; WO2007/2181 A2, 2007) were added, and the reaction mixture was stirred at RT overnight. 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine were added, and the mixture was stirred at RT for 24 h. Another 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine and 5.0 g (15.3 mmol) of caesium carbonate were then added, and the mixture was stirred at 60 C. for 12 h. The reaction mixture was added carefully to 2.3 l of 0.5 M aqueous hydrochloric acid. The mixture was extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases were washed with 500 ml of saturated aqueous sodium chloride solution, dried and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (mobile phase: cyclohexane/ethyl acetate gradient: 9/1 to 7/3). This gave 29.8 g (92% of theory) of the target compound. LC-MS (Method 1): Rt=0.94 min. MS (ESIpos): m/z=284 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta=5.59 (d, 2H), 7.53-7.60 (m, 1H), 7.80-7.87 (m, 1H), 8.26 (d, 1H), 8.40-8.47 (m, 2H).
92%	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃;	20.0 g (114.6 mmol) of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> from Example 38A and 56.0 g (171.9 mmol) of caesium carbonate were initially charged in 319 ml of DMF. 17.51 g (120.3 mmol) of 2-(chloromethyl)-3-fluoropyridine (commercially available; additionally described in: K. Weidmann et al. Journal of Medicinal Chemistry 1992, 35, 438-450; U.S. Pat. No. 5,593,993, 1997; WO2007/2181 A2, 2007) were added and the reaction mixture was stirred at RT overnight. 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine were added and the mixture was stirred at RT for 24 h. Subsequently, another 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine and 5.0 g (15.3 mmol) of caesium carbonate were added and the mixture was stirred at 60 C. for 12 h. The reaction mixture was added carefully to 2.3 l of 0.5 M of aqueous hydrochloric acid. The mixture was extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases were washed with 500 ml of saturated aqueous sodium chloride solution, dried and concentrated under reduced pressure. The crude product was purified by means of silica gel chromatography (mobile phase: cyclohexane/ethyl acetate gradient: 9/1 to 7/3). This gave 29.8 g (92% of theory) of the target compound. LC-MS (Method 1): Rt=0.94 min. MS (ESIpos): m/z=284 (M+H)+. 1H-NMR (400 Mhz, DMSO-d6): delta=5.59 (d, 2H), 7.53-7.60 (m, 1H), 7.80-7.87 (m, 1H), 8.26 (d, 1H), 8.40-8.47 (m, 2H).
29.8 g	With caesium carbonate; In N,N-dimethyl-formamide; at 20 - 60℃;	Example 28A 5-Chloro-3-[(3-fluoropyridin-2-yl)methoxy]-2-nitropyridine 20.0 g (114.6 mmol) of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> from Example 27A and 56.0 g (171.9 mmol) of caesium carbonate were initially charged in 319 ml of DMF. 17.51 g (120.3 mmol) of 2-(chloromethyl)-3-fluoropyridine (commercially available; additionally described in: K. Weidmann et al. Journal of Medicinal Chemistry 1992, 35, 438-450; U.S. Pat. No. 5,593,993, 1997; WO2007/2181 A2, 2007) were added and the reaction mixture was stirred at RT overnight. 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine were added and the mixture was stirred at RT for 24 h. Subsequently, another 6.0 g (41.2 mmol) of 2-(chloromethyl)-3-fluoropyridine and 5.0 g (15.3 mmol) of caesium carbonate were added and the mixture was stirred at 60 C. for 12 h. The reaction mixture was added carefully to 2.3 l of 0.5 M aqueous hydrochloric acid. The mixture was extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases were washed with 500 ml of saturated aqueous sodium chloride solution, dried and concentrated under reduced pressure. The crude product was purified by means of silica gel chromatography (mobile phase: cyclohexane/ethyl acetate gradient: 9/1 to 7/3). This gave 29.8 g (92% of theory) of the target compound. LC-MS (Method D): Rt=0.94 min. MS (ESIpos): m/z=284 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta=5.59 (d, 2H), 7.53-7.60 (m, 1H), 7.80-7.87 (m, 1H), 8.26 (d, 1H), 8.40-8.47 (m, 2H).

References: [1]Patent: US2014/128386,2014,A1 .Location in patent: Paragraph 1463; 1464; 1465; 1466; 1467.
[2]Patent: US2017/304278,2017,A1 .Location in patent: Paragraph 0701; 0702; 0703; 0704; 0705.
[3]Patent: US2017/50961,2017,A1 .Location in patent: Paragraph 0934; 0935; 0936; 0937; 0938.

21
[ 936247-35-7 ]
[ 85118-00-9 ]
[ 1609082-28-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 16A 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine 33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 15A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1N aqueous hydrochloric acid and the solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (quint., 1H); 8.28 (d, 1H); 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 8A 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine 33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 12A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into a water/1N aqueous hydrochloric acid mixture. The solid obtained was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 13A 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine 33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 12A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).

97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 7A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H), 7.22 (t, 2H), 7.58 (q, 1H), 8.28 (d, 1H), 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	Example 8A 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine 33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 7A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1 N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 4A;189 mmol, 1 equivalent) and 61.6 g of caesium carbonate(189 mmol, 1 equivalent) were initially charged in 528 ml ofDMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1equivalent) were added and the mixture was stirred at RTovernight. The reaction mixture was stirred into water/iNaqueous hydrochloric acid. The solid was filtered off,washed with water and air-dried. This gave 54.9 g (97% oftheory) of the title compound. ?H-NMR (400 MHz, DMSO-d5): oe=5.46 (s, 2H);7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example 1A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into water/1N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound. 1H-NMR (400 MHz, DMSO-d6): delta=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (q, 1H); 8.28 (d, 1H); 8.47 (d, 1H).
97%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;	33 g of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (Example12A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into a mixture of water/iN hydrochloric acid, and the crystals were filtered off with suction, washed with water and air-dried. 54.9 g (97% of theory) of the title compound were obtained. j0377] ?H-NMR (400 MHz, DMSO-d5): oe=5.46 (s, 2H); 7.22 (t, 2H); 7.58 (quint., 1H); 8.28 (d, 1H); 8.47 (d, 1H).

References: [1]Patent: US2014/128386,2014,A1 .Location in patent: Paragraph 1057; 1058; 1059.
[2]Patent: US2014/128425,2014,A1 .Location in patent: Paragraph 0389-0400.
[3]Patent: US2014/128372,2014,A1 .Location in patent: Paragraph 0419; 0420; 0421.
[4]Patent: US2016/122341,2016,A1 .Location in patent: Paragraph 0550; 0551; 0552.
[5]Patent: US2017/57954,2017,A1 .Location in patent: Paragraph 0547; 0548; 0549.
[6]Patent: US2016/347770,2016,A1 .Location in patent: Paragraph 0527; 0528; 0529.
[7]Patent: US2017/57958,2017,A1 .Location in patent: Paragraph 0202-0204.
[8]Patent: US2016/362408,2016,A1 .Location in patent: Paragraph 0375; 0376; 0377.

22
[ 936247-35-7 ]
[ 1609164-89-7 ]

References: [1]Patent: US2014/128386,2014,A1 .

23
[ 936247-35-7 ]
[ 1609165-45-8 ]

References: [1]Patent: US2014/128386,2014,A1 .

24
[ 936247-35-7 ]
[ 1609165-51-6 ]

References: [1]Patent: US2014/128386,2014,A1 .

25
[ 936247-35-7 ]
[ 1609348-02-8 ]
[ 1609348-03-9 ]

References: [1]Patent: US2014/128372,2014,A1 .

26
[ 936247-35-7 ]
[ 1609341-91-4 ]
[ 1609341-92-5 ]

References: [1]Patent: US2014/128372,2014,A1 .

27
[ 936247-35-7 ]
tert-butyl {4-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}-carbonyl)amino]-2-methylbutan-2-yl}carbamate trifluoroacetate [ No CAS ]

References: [1]Patent: US2014/128372,2014,A1 .

28
[ 936247-35-7 ]
[ 106-95-6 ]
5-chloro-2-nitro-3-(prop-2-en-1-yloxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		Toa solution of <strong>[936247-35-7]5-chloro-2-nitropyridin-3-ol</strong> (1.5 g, 8.59 mmol) in acetonitrile(30 mL) was added K2CO3 (2.38 g, 17.2 mmol) and themixture stirred for 15 mins followed by dropwise addition of 3-bromoprop-l-ene(1.25 g, 10.31 mmol). The reaction mixture was re fluxed for 16 hrs, cooled andfiltered. The filtrate was concentrated and the residue purified by flashsilica chromatography (eluent 1 :9 EtOAc) to afford the title compound as ayellow solid (1.40 g, 76%); H NMR (400 MHz, CDC13) delta4.72 (dt, 2H), 5.45 (m, 2H), 6.01 (m, 1H), 7.50 (d, 1H), 8.04 (d,lH).

References: [1]Patent: WO2014/184234,2014,A1 .Location in patent: Page/Page column 69.

29
[ 936247-35-7 ]
N-(5-chloro-3-hydroxypyridin-2-yl)-1-(3,5-dimethoxyphenyl)methanesulfonamide [ No CAS ]

References: [1]Patent: WO2014/184234,2014,A1 .

30
[ 936247-35-7 ]
5-chloro-3-(prop-2-en-1-yloxy)pyridin-2-amine [ No CAS ]

References: [1]Patent: WO2014/184234,2014,A1 .

31
[ 936247-35-7 ]
N-[5-chloro-3-(prop-2-en-1-yloxy)pyridin-2-yl]-1-(3,5-dimethoxyphenyl)methanesulfonamide [ No CAS ]

References: [1]Patent: WO2014/184234,2014,A1 .

32
[ 936247-35-7 ]
tert-butyl 4-{4-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-3-methylphenyl}piperazine-1-carboxylate [ No CAS ]

References: [1]Patent: US2016/362408,2016,A1 .

33
[ 936247-35-7 ]
tert-butyl {2-[({6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]benzyl}carbamate trifluoroacetate [ No CAS ]

References: [1]Patent: US2016/362408,2016,A1 .

34
[ 936247-35-7 ]
6-chloro-8-[(2,6-difluorobenzyl)oxy]-N-(3,5-dimethyl-1,2-oxazol-4-yl)-2-methylimidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

References: [1]Patent: US2016/362408,2016,A1 .

35
[ 936247-35-7 ]
6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(5-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]
6-chloro-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(3-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide [ No CAS ]

References: [1]Patent: US2016/362408,2016,A1 .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Jones Oxidation • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Martin's Sulfurane Dehydrating Reagent • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Preparation of Alcohols • Preparation of Amines • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation

Related Functional Groups of
[ 936247-35-7 ]

Chlorides

A345583 [52092-47-4]

5-Chloro-2-nitropyridine

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Alcohols

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Similarity: 0.75

Nitroes

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Related Parent Nucleus of
[ 936247-35-7 ]

Pyridines

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2-Nitropyridin-3-ol

Similarity: 0.86

A361015 [20265-37-6]

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P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 936247-35-7

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CAS No.: 936247-35-7

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[ 936247-35-7 ]

Chlorides

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Pyridines

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{[proInfo.proName]}

CAS No.: 936247-35-7

{[proInfo.proName]}

CAS No.: 936247-35-7

Alternative Products

Product Details of [ 936247-35-7 ]

Safety of [ 936247-35-7 ]

Computational Chemistry of [ 936247-35-7 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 936247-35-7 ]

[ 936247-35-7 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 936247-35-7 ]

Chlorides

Alcohols

Nitroes

Related Parent Nucleus of [ 936247-35-7 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 936247-35-7 ]

Related Parent Nucleus of
[ 936247-35-7 ]