[ CAS No. 19959-77-4 ] {[proInfo.proName]}

Name: 19959-77-4|2-(5-Methyl-1H-pyrazol-3-yl)pyridine|95%
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Quality Control of [ 19959-77-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19959-77-4 ]

SDS Specification

Alternatived Products of [ 19959-77-4 ]

Product Details of [ 19959-77-4 ]

CAS No. :	19959-77-4	MDL No. :	MFCD11840239
Formula :	C₉H₉N₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KFJQEHNCMPSEJG-UHFFFAOYSA-N
M.W :	159.19	Pubchem ID :	2755568
Synonyms :

Calculated chemistry of [ 19959-77-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.11
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.78
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.24
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	0.58
Log Po/w (SILICOS-IT) :	2.54
Consensus Log Po/w :	1.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.22
Solubility :	0.958 mg/ml ; 0.00602 mol/l
Class :	Soluble
Log S (Ali) :	-1.71
Solubility :	3.1 mg/ml ; 0.0195 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.75
Solubility :	0.028 mg/ml ; 0.000176 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.01

Safety of [ 19959-77-4 ]

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 [ 19959-77-4 ]

* 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 [ 19959-77-4 ]
Downstream synthetic route of [ 19959-77-4 ]

[ 19959-77-4 ] Synthesis Path-Upstream 1~5

1
[ 1031694-63-9 ]
[ 19959-77-4 ]

Reference： [1] Journal of the American Chemical Society, 1998, vol. 120, # 40, p. 10391 - 10396

2
[ 40614-52-6 ]
[ 19959-77-4 ]

Reference： [1] Journal of Chemical Research, 2009, # 2, p. 72 - 74
[2] Tetrahedron, 2005, vol. 61, # 52, p. 12377 - 12385

3
[ 2524-52-9 ]
[ 19959-77-4 ]

Reference： [1] Journal of the American Chemical Society, 1998, vol. 120, # 40, p. 10391 - 10396

4
[ 93-91-4 ]
[ 19959-77-4 ]

Reference： [1] Medicinal Chemistry letters, 2012, vol. 3, # 8, p. 678 - 682,5
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 8, p. 678 - 682

5
[ 1122-62-9 ]
[ 19959-77-4 ]

Reference： [1] Tetrahedron, 2005, vol. 61, # 52, p. 12377 - 12385

[ 19959-77-4 ] Synthesis Path-Downstream 1~34

1
[ 40614-52-6 ]
[ 19959-77-4 ]

Yield	Reaction Conditions	Operation in experiment
80.8%	With hydrazine hydrate for 13h; Heating;
	With hydrazine hydrate In ethanol for 5h; Heating; Yield given;
4 g	With hydrazine In ethanol for 2h; Heating;

	With hydrazine In ethanol for 5h; Reflux; Inert atmosphere;
	With hydrazine hydrate In methanol for 2h; Reflux;	18.3 (3) Preparation of 3-methyl-5-o-pyridyl-1-hydropyrazole Add a 100ml round bottom flask to the magnetizer. 1-o-pyridylbutane-1,3-dione (3.26 g, 20 mmol, 1.0 eq) and hydrazine hydrate (1.1 g, 20 mmol, 1.0 eq) were added inward, followed by methanol 50 ml, heated under reflux for 2 h, extracted with ethyl acetate Silica gel column chromatography gave 3-methyl-5-o-pyridyl-1-hydropyrazole
	With hydrazine hydrate In ethanol for 24h; Reflux;
	With hydrazine hydrate In ethanol for 24h; Reflux; Inert atmosphere;
	With hydrazine In ethanol Inert atmosphere;
	With hydrazine In ethanol at 80℃;

Reference： [1]Ferles, Miloslav; Kafka, Stanislav; Silhankova, Alexandra; Sputova, Michaela [Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1167 - 1172]
[2]Thiel, Werner R.; Eppinger, Joerg [Chemistry - A European Journal, 1997, vol. 3, # 5, p. 696 - 705]
[3]Yu, Wei-Shan; Cheng, Chung-Chih; Cheng, Yi-Ming; Wu, Pei-Chi; Song, Yi-Hwa; Chi, Yun; Chou, Pi-Tai [Journal of the American Chemical Society, 2003, vol. 125, # 36, p. 10800 - 10801]
[4]Muller, Keven; Sun, Yu; Heimermann, Andreas; Menges, Fabian; Niedner-Schatteburg, Gereon; Van Wuellen, Christoph; Thiel, Werner R. [Chemistry - A European Journal, 2013, vol. 19, # 24, p. 7825 - 7834]
[5]Current Patent Assignee: LANZHOU UNIVERSITY - CN108203408, 2018, A Location in patent: Paragraph 0030
[6]Su, Ning; Lu, Guang-Zhao; Zheng, You-Xuan [Journal of Materials Chemistry C, 2018, vol. 6, # 21, p. 5778 - 5784]
[7]Su, Ning; Wu, Zheng-Guang; Zheng, You-Xuan [Dalton Transactions, 2018, vol. 47, # 22, p. 7587 - 7593]
[8]Su, Ning; Zheng, You-Xuan [Journal of Organometallic Chemistry, 2018, vol. 876, p. 35 - 42]
[9]Li, Shuaibing; Qu, Junle; Song, Jun; Su, Ning; Yang, Kun; Zhou, Feifan; Zhou, Liang [Dyes and Pigments, 2021, vol. 195]

2
[ 1031694-63-9 ]
[ 19959-77-4 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 10391 - 10396

3
[ 40614-52-6 ]
[ 19959-77-4 ]

Reference： [1]Journal of Chemical Research,2009,p. 72 - 74
[2]Tetrahedron,2005,vol. 61,p. 12377 - 12385

4
[ 19959-77-4 ]
[ 629-27-6 ]
2-(5-methyl-2-octyl-2<i>H</i>-pyrazol-3-yl)-pyridine [ No CAS ]
2-(5-methyl-1-octyl-1H-pyrazol-3-yl)-pyridine [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 12377 - 12385

5
[ 19959-77-4 ]
[ 75-03-6 ]
2-(1-ethyl-5-methyl-1H-pyrazol-3-yl)-pyridine [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 12377 - 12385

6
[ 1122-62-9 ]
[ 19959-77-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 12377 - 12385

7
[ 2524-52-9 ]
[ 19959-77-4 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 10391 - 10396

8
[ 14104-20-2 ]
[ 19959-77-4 ]
bis(η3-allyl-μ-chloropalladium(II)) [ No CAS ]
[ 215323-63-0 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 10391 - 10396

9
N,N-dimethyl-(S)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine [ No CAS ]
[ 19959-77-4 ]
1-((S)-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethyl)-5-methyl-3-(2-pyridyl)-1H-pyrazole [ No CAS ]

Reference： [1]Organometallics,1995,vol. 14,p. 5415 - 5425

10
[ 13869-38-0 ]
[ 19959-77-4 ]
[ 842123-38-0 ]

Reference： [1]Inorganica Chimica Acta,2005,vol. 358,p. 617 - 622

11
[ 12107-56-1 ]
[ 19959-77-4 ]
[ 261921-49-7 ]

Reference： [1]Inorganica Chimica Acta,2005,vol. 358,p. 617 - 622

12
[ 21264-30-2 ]
[ 19959-77-4 ]
[ 261921-49-7 ]

Reference： [1]Inorganica Chimica Acta,2005,vol. 358,p. 617 - 622

13
[ 19959-77-4 ]
[ 855343-76-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	With N-chloro-succinimide; In acetonitrile; at 70℃; for 14.0h;	Synthesis of 2-(4-chloro-5-methyl-lH-pyrazol-3-yl)pyridine [00118] Preparation 2: A solution of 2-(5-methyl-lH-pyrazol-3-yl)pyridine (500mg, 3.15 mmol) in acetonitrile (912 mL) was treated with N-chlorosuccinimide in 6 portions and the resulting mixture stirred at 70 0C for 14 h. The mixture was cooled and then concentrated in vacuo to yield a residue. The residue was partitioned between EtOAc (8 mL) and H2O (3 mL). The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to yield a residue. The residue was purified by flash chromatography on silica gel using 20-80% EtOAc in hexanes to give the title compound (300 mg, 53 %).

Reference： [1]Patent: WO2008/42925,2008,A1 .Location in patent: Page/Page column 54

14
[ 19959-77-4 ]
[ 105-36-2 ]
[ 1187755-93-6 ]
[ 1187755-92-5 ]

Reference： [1]Journal of Chemical Research,2009,p. 72 - 74

15
[ 22840-91-1 ]
[ 19959-77-4 ]
[ 1239344-60-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: methyl-3(5) α-pyridyl-5(3) pyrazole With sodium hydride In tetrahydrofuran at 20℃; for 1.5h; Stage #2: trans-[dichloroplatinum(II)bis(N,N-dimethylsulfoxide)] In tetrahydrofuran for 12h; Heating / reflux;	4 Synthesis of Pt(mppz)2 (4) To the suspension of NaH (15 mg, 0.63 mmol) in 15 mL of THF was added 3-methyl-5-(2-pyridyl) pyrazole (mppzH, 83 mg, 0.52 mmol) slowly at room temperature. After being stirred for 1.5 hour, the solution was filtered and transferred into a reaction flask loaded with 100 mg of Pt(DMSO)2Cl2 (0.24 mmol) and 10 mL of THF. The solution was refluxed for 12 hours. After then, the solvent was evaporated under vacuum and 60 mL of CH2Cl2 was added to extract the product. The extract was then washed with water, dried with anhydrous Na2SO4, giving a yellowish green material after removal of all solvent. Further purification was conducted using vacuum sublimation (160° C., 220 mtorr), affording 80 mg of Pt(mppz)2 as bright green solid (0.16 mmol, 65%).Spectra data of (4): MS (EI, 70 eV), observed m/z (actual) [assignment]: 511 (511) [M+]. 1H NMR (500 MHz, CDCl3, 294 K): δ 10.64 (d, 3JHH=6.0 Hz, 2H), 7.86 (t, 3JHH=8.0 Hz, 3JHH=8.0 Hz, 2H), 7.55 (d, 3JHH=8.0 Hz, 2H), 7.28 (t, 3JHH=6.0 Hz, 3JHH=6.0 Hz, 2H), 6.43 (s, 2H), 2.45 (s, 6H). 13C NMR (125 MHz, CDCl3, 294K): δ 154.7 (Cpy), 152.5 (Cpz), 150.3 (CHpy), 147.6 (Cpz), 139.1 (CHpy), 121.6 (CHpy), 118.2 (CHpy), 103.0 (CHpz), 14.0 (CH3). Anal. Calcd. for C18H16N6Pt: C, 42.27; N, 16.43; H, 3.15. Found: C, 42.08; N, 16.38; H, 3.49.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - US7002013, 2006, B1 Location in patent: Page/Page column 17

16
[ 19959-77-4 ]
[ 1257268-30-6 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 8772 - 8777

17
1-(2-pyridyl)-1-buten-3-one [ No CAS ]
[ 19959-77-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; toluene-4-sulfonic acid hydrazide; sodium hydroxide; In water; at 80℃; for 10.0h;Air atmosphere;	General procedure: A Schlenk tube with a magnetic stir bar charged with alpha,beta-unsaturated carbonyl compounds (0.5 mmol, 1 equiv), tosyl hydrazide (0.6 mmol, 1.2 equiv), NaOH (1.5 equiv), (n-Bu)4NBr (1.5 equiv). The reaction vessel was placed in an 80 C oil bath, and then stirring at this temperature for 10 h. The reaction mixture was then allowed to cool to ambient temperature, and diluted with 20 mL of ethyl acetate, and washed with brine (15 mL), water (15 mL), and then the organic layer was dried over Na2SO4. After concentrated in vacuo, the crude product was purified by column chromatography. The identity and purity of the known product was confirmed by 1H NMR, 13C NMR, and GC-MS.

Reference： [1]Tetrahedron,2011,vol. 67,p. 9618 - 9621

18
[ 19959-77-4 ]
[ 24424-99-5 ]
C₁₄H₁₇N₃O₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 678 - 682,5

19
[ 19959-77-4 ]
[ 24424-99-5 ]
C₁₄H₁₆BrN₃O₂ [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 678 - 682,5

20
[ 93-91-4 ]
[ 19959-77-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 678 - 682,5

21
[ 19959-77-4 ]
[ 7646-85-7 ]
[Zn(2-(5-methyl-1H-pyrazol-3-yl)pyridine)Cl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In ethanol; for 0.25h;	A 5mL ethanol solution of L (0.2mmol, 15.9mg) and Et3N (0.1mmol, 14mul) was mixed with a 5mL ethanol solution of ZnCl2 (0.1mmol, 13.6mg), and the resulting mixture was then stirred for 15min to obtain a colorless solution. This colorless solution was filtered and left to evaporate for three days, giving rise to colorless rod-like crystals. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 23.6mg (80%), M. p. >300C. Anal. Calc. for C9H9Cl2N3Zn (FW, 295.46): C, 36.58; H, 3.07; N, 14.22. Found: C, 36.08; H, 3.53; N, 13.79%. Selected IR data (KBr, cm-1): 3175(s), 3133 (s), 3109 (m), 3087 (m), 2924 (s), 2853 (s), 1611 (m) (nu(C=N)), 1573 (m) (delta(C=C)), 1446 (s) (nu(CH3)), 1303 (m) (nu(C-N)), 1261 (w), 1114 (w), 1053 (w), 1023(w), 988 (s), 823 (m), 793 (s), 738 (m).

Reference： [1]Polyhedron,2014,vol. 81,p. 705 - 714

22
[ 19959-77-4 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[Mn(2-(5-methyl-1H-pyrazol-3-yl)pyridine₎₂]*3H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In ethanol; for 0.25h;	General procedure: A 5mL ethanol solution of L (0.2mmol, 15.9mg) and Et3N (0.1mmol, 14mul) was mixed with a 5mL ethanol solution of ZnCl2 (0.1mmol, 13.6mg), and the resulting mixture was then stirred for 15min to obtain a colorless solution. This colorless solution was filtered and left to evaporate for three days, giving rise to colorless rod-like crystals. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 23.6mg (80%),

Reference： [1]Polyhedron,2014,vol. 81,p. 705 - 714

23
[ 19959-77-4 ]
[ 121-91-5 ]
[ 4247-36-3 ]
[Mn(2-(5-methyl-1H-pyrazol-3-yl)pyridine)₂(m-phthalic acid)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In methanol; for 0.25h;	A 5mL methanol solution of L (0.2mmol, 31.8mg) and m-phthalic acid (0.2mmol, 33.2mg) was mixed with a 5mL methanol solution of Mn(HCOO)2·2H2O (0.1mmol, 14.5mg), and the resulting mixture was then stirred 15min to obtain a colorless solution. This colorless solution was filtered and left to evaporate for one week, giving rise to colorless stick-like crystals. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 47.1mg (67%), M. p. > 300C. Anal. Calc. for C34H28MnN6O8 (FW, 703.56): C, 58.04; H, 4.01; N, 11.95. Found: C, 58.98; H, 4.73; N, 11.49%. Selected IR data (cm-1, KBr): 3256 (b, s), 3128 (m), 3073 (m), 2925 (m), 2883 (m), 1694 (s) (nu(C=O)), 1606 (m) (nu(C=N)), 1561 (s) (nu(C=C)), 1428 (m) (delta(CH3)), 1392 (s), 1296 (m) (nu(C-N)), 1161 (w), 777 (m), 733 (m), 689 (m).

Reference： [1]Polyhedron,2014,vol. 81,p. 705 - 714

24
[ 19959-77-4 ]
nickel(II) chloride hexahydrate [ No CAS ]
[ 7803-57-8 ]
[Ni(2-(5-methyl-1H-pyrazol-3-yl)pyridine)₂(H₂O)₂]Cl₂*0.5N₂H₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With triethylamine; In ethanol; for 0.25h;	A 5mL ethanol solution of L (0.1mmol, 15.9mg), hydrazine hydrate (0.1mmol, 5mg) and Et3N (0.1mmol, 14mul) was mixed with a 5mL ethanol solution of NiCl2·6H2O (0.05mmol, 11.9mg), and the resulting mixture was then stirred for 15min to obtain a light-green solution. This resulting solution was filtered and left to evaporate for three days, giving rise to light-blue block crystals of 2. The resulting crystals were washed with n-hexane 2?3 times, then dried in vacuum. Yield: 26.4mg (53%), M. p. >300C. Anal. Calc. for C18H24Cl2N7NiO2 (FW, 500.05): C, 43.37; H, 4.86; N, 19.68. Found: C, 43.54; H, 4.96; N, 19.18%. Selected IR data (cm-1, KBr): 3350 (b, m), 3250 (b, s), 3130 (s), 3066 (s), 2969 (s), 2863 (s), 1610 (m) (nu(C=N)), 1573 (m) (nu(C=C)), 1443 (s) (delta(CH3)), 1304 (m) (nu(C-N)), 1256 (w), 1116 (w), 1054 (w), 1021(w), 985 (m), 789 (s).

Reference： [1]Polyhedron,2014,vol. 81,p. 705 - 714

25
[ 19959-77-4 ]
cadmium(II) nitrate tetrhydrate [ No CAS ]
[Cd(2-(5-methyl-1H-pyrazol-3-yl)pyridine)₂(NO₃)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In acetonitrile; for 168.0h;	Solid ligand L (0.2mmol, 31.8mg) and Cd(NO3)2·4H2O (0.1mmol, 30.8mg) were placed into the bottom of separate arms of an H-tube. The H-tube was filled with acetonitrile solution and sealed with plastic film. After one week, colorless stick-like crystals of compound 4 were generated and collected, washed with n-hexane 2-3 times, then dried in vacuum. Yield: 42.72mg (77%), M. p. > 300C. Anal. Calc. for C18H18CdN8O6 (FW, 554.8): C, 38.97; H, 3.27; N, 20.20. Found: C, 38.31; H, 3.39; N, 19.70%. Selected IR data (cm-1, KBr): 3200 (b, s), 3135 (s), 2994 (s), 2853 (m), 2363 (s), 1607 (m) (nu(C=N)), 1578 (m) (nu(C=C)), 1435 (s), 1387 (s), 1340 (m), 1301 (m), 1225 (w), 1156 (w), 1111 (w), 1018 (w), 980 (s), 797 (s), 740 (m).

Reference： [1]Polyhedron,2014,vol. 81,p. 705 - 714

26
copper(II) choride dihydrate [ No CAS ]
[ 19959-77-4 ]
[Cu₂(μ-L)₂Cl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In ethanol; acetone; for 336.0h;Sealed tube;	Solid HL (15.9 mg, 0.10 mmol) and CuCl22H2O (16.8 mg,0.10 mmol) were separated into two arms of an H-tube, whichwas filled with ethanol or acetone solution and subsequentlysealed with thin film. Dark blue block crystals of complex 1 wereobtained after two weeks. The crystals were washed with n-hexane2 3 times, then dried in a vacuum. Yield: 27.3 mg (53%). M.p.>300 C. Anal. Calc. for C18H16N6Cl2Cu2 (FW, 514.3): C, 42.03; H,3.14; N, 16.34. Found: C, 42.34; H, 3.54; N, 16.28%. Selected IR data(cm-1, KBr): 3525 (b, s); 3080 (w); 2923 (w); 1610 (vs m(CN));1565 (m, m(CC)); 1492 (m); 1457 (vs d(CH3)); 1400 (m); 1336(m); 1285 (m); 1177 (m); 1152 (m); 1115 (m); 1088 (m); 1053(m); 985 (m); 897 (m); 782 (vs); 748 (m); 683 (m); 648 (m); 532(w).

Reference： [1]Polyhedron,2017,vol. 128,p. 104 - 111

27
copper(II) nitrate trihydrate [ No CAS ]
[ 19959-77-4 ]
[Cu₂(μ-L)₂(NO₃)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine; In acetone; acetonitrile; for 336.0h;Sealed tube;	General procedure: Solid HL (15.9 mg, 0.10 mmol) and CuCl22H2O (16.8 mg,0.10 mmol) were separated into two arms of an H-tube, whichwas filled with ethanol or acetone solution and subsequentlysealed with thin film. Dark blue block crystals of complex 1 wereobtained after two weeks. The crystals were washed with n-hexane2 3 times, then dried in a vacuum.

Reference： [1]Polyhedron,2017,vol. 128,p. 104 - 111

28
[ 19959-77-4 ]
[ 6046-93-1 ]
[Cu₂(μ-L)₂(CH₃COO)₂] [ No CAS ]