[ CAS No. 18368-73-5 ]

Name: 18368-73-5|3-Methyl-2-nitropyridine|98%
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Quality Control of [ 18368-73-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18368-73-5 ]

SDS Specification

Alternatived Products of [ 18368-73-5 ]

Product Details of [ 18368-73-5 ]

CAS No. :	18368-73-5	MDL No. :	MFCD00971950
Formula :	C₆H₆N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NNHSGPKSSZLCGT-UHFFFAOYSA-N
M.W :	138.12	Pubchem ID :	564205
Synonyms :

Calculated chemistry of [ 18368-73-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.02
TPSA :	58.71 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.24
Log Po/w (XLOGP3) :	1.38
Log Po/w (WLOGP) :	1.3
Log Po/w (MLOGP) :	0.41
Log Po/w (SILICOS-IT) :	-0.35
Consensus Log Po/w :	0.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.94
Solubility :	1.57 mg/ml ; 0.0114 mol/l
Class :	Very soluble
Log S (Ali) :	-2.22
Solubility :	0.84 mg/ml ; 0.00608 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.76
Solubility :	2.38 mg/ml ; 0.0172 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 18368-73-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18368-73-5 ]

* 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 [ 18368-73-5 ]
Downstream synthetic route of [ 18368-73-5 ]

[ 18368-73-5 ] Synthesis Path-Upstream 1~1

1
[ 18368-73-5 ]
[ 33225-72-8 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 3167

[ 18368-73-5 ] Synthesis Path-Downstream 1~22

1
[ 1603-40-3 ]
[ 18368-73-5 ]

Yield	Reaction Conditions	Operation in experiment
89%		Example 1; Synthesis of 3-amino-1-hydroxy-3,4-dihydro-1,8-naphthyridin-2(1H)-one, trifluoroacetate salt (8); 3-Methyl-2-nitropyridine (2); To a solution of H2O2 (120 g, 1.1 mol) in fuming sulfuric acid (250 mL) was added a solution of 3-methylpyridin-2-amine (1) (16 g, 0.15 mol) in concentrated sulfuric acid (50 mL) drop-wise, while keeping the reaction temperature at 0 C. After stirring for 3 h at 10-25 C., the reaction mixture was brought to pH=11-12 by adding an aqueous 40% NaOH solution at 0-5 C. The resulting mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over Na2SO4 and filtered. The solvent was removed in vacuo to give the desired compound (18.2 g, 89%) as a yellow oil.
13.13%	With sulfuric acid; dihydrogen peroxide; at 20℃; for 29.0h;Cooling with ice;	Hydrogen peroxide (187.5 g, 1.72 mol) was dissolved in 390 mL fuming sulfuric acid,2-amino-3-methylpyridine (25 g, 0.23 mmol) was dissolved in 80 mL of concentrated sulfuric acid under stirring,And dropping into the solution dropwise under ice-cooling,In the ice bath conditions for 5h,Returned to room temperature for 24 h.With 40% sodium hydroxide aqueous solution to adjust the pH to neutral, with ethyl acetate(700 mL X 3). The extract was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated to a crude product,The crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:10) to give 2-nitro-2-methylpyridine (4.2 g, 13.13%).

Reference： [1]Patent: US2010/324043,2010,A1 .Location in patent: Page/Page column 25
[2]Advanced Synthesis and Catalysis,1997,vol. 339,p. 335 - 339
[3]Patent: CN106749045,2017,A .Location in patent: Paragraph 0298-0299
[4]Journal of the American Chemical Society,1951,vol. 73,p. 494
[5]Organic Letters,2012,vol. 14,p. 5618 - 5620

2
[ 18368-73-5 ]
[ 33225-72-8 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 3167

3
[ 100047-38-9 ]
[ 67-66-3 ]
[ 7719-12-2 ]
[ 18368-73-5 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 3565

4
[ 1603-40-3 ]
[ 7722-84-1 ]
H2SO4 <SO3 containing> [ No CAS ]
[ 18368-73-5 ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 494

5
[ 18368-73-5 ]
[ 15936-06-8 ]

Yield	Reaction Conditions	Operation in experiment
44.14%	With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide; at 100℃; for 48.0h;	2-nitro 2-methylpyridine (4.2 g, 30.66 mmol) was dissolved in 100 mL of carbon tetrachloride,N-bromosuccinimide (5.5 g, 30.66 mmol) was added,Add the catalyst amount of the photoinitiator dibenzoyl peroxide, heat up to 100 C and reflux for 48 h.The reaction solution was returned to room temperature, the solvent was removed by distillation under reduced pressure, 50 mL of ice water was added,Extracted with ethyl acetate (40 mL X3). The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to a crude product. The crude product was purified by silica gel column chromatography (ethyl acetateEster: petroleum ether = 1: 10) 3-Bromoethyl-2-nitropyridine (2.9 g, 44.14%).
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;Reflux;	3-(Bromomethyl)-2-nitropyridine (3); A solution of <strong>[18368-73-5]3-methyl-2-nitropyridine</strong> (2) (12.4 g, 90.0 mmol), NBS (16.0 g, 90.4 mmol) and AIBN (0.5 g, 3.0 mmol) in 0014 (50 mL) was refluxed overnight. TLC (Eluant: 20:1 petroleum ether/EtOAc) showed that most of the starting material had been consumed. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue (12.6 g), which was used in the next step without purification.

Reference： [1]Patent: CN106749045,2017,A .Location in patent: Paragraph 0300
[2]Patent: US2010/324043,2010,A1 .Location in patent: Page/Page column 25-26

6
[ 18368-73-5 ]
[ 33421-28-2 ]