[ CAS No. 600727-96-6 ] {[proInfo.proName]}

Name: 600727-96-6|2,6-Di(1H-pyrazol-1-yl)isonicotinic acid|98%
Brand: Ambeed
SKU: A1156790
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Quality Control of [ 600727-96-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 600727-96-6 ]

SDS Specification

Alternatived Products of [ 600727-96-6 ]

Product Details of [ 600727-96-6 ]

CAS No. :	600727-96-6	MDL No. :	MFCD34165562
Formula :	C₁₂H₉N₅O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AABBIGVHMABWQY-UHFFFAOYSA-N
M.W :	255.23	Pubchem ID :	12120400
Synonyms :

Safety of [ 600727-96-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 600727-96-6 ]

* 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 [ 600727-96-6 ]

[ 600727-96-6 ] Synthesis Path-Downstream 1~51

1
[ 288-13-1 ]
[ 2016-99-1 ]
[ 600727-96-6 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 5039 - 5045

2
[ 112-92-5 ]
[ 600727-96-6 ]
octadecyl 2,6-di(pyrazol-1-yl)pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; dicyclohexyl-carbodiimide In dichloromethane
51%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

Reference： [1]Vermonden, Tina; Branowska, Danuta; Marcelis, Antonius T. M.; Sudhölter, Ernst J. R. [Tetrahedron, 2003, vol. 59, # 27, p. 5039 - 5045]
[2]Galadzhun, Iurii; Kulmaczewski, Rafal; Cespedes, Oscar; Yamada, Mihoko; Yoshinari, Nobuto; Konno, Takumi; Halcrow, Malcolm A. [Inorganic Chemistry, 2018, vol. 57, # 21, p. 13761 - 13771]

3
[ 64-17-5 ]
[ 600727-96-6 ]
[ 600727-97-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid for 4h; Heating;
74%	With sulfuric acid for 3h; Heating;

Reference： [1]Location in patent: experimental part Basak, Supratim; Hui, Pramiti; Chandrasekar, Rajadurai [Synthesis, 2009, # 23, p. 4042 - 4048]
[2]Vermonden, Tina; Branowska, Danuta; Marcelis, Antonius T. M.; Sudhölter, Ernst J. R. [Tetrahedron, 2003, vol. 59, # 27, p. 5039 - 5045]

4
[ 600727-96-6 ]
[ 504-63-2 ]
1,3-propyl bis-[2,6-di(1H-pyrazol-1-yl)isonicotinate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With dmap In dichloromethane for 48h;

Reference： [1]Vermonden, Tina; Branowska, Danuta; Marcelis, Antonius T. M.; Sudhölter, Ernst J. R. [Tetrahedron, 2003, vol. 59, # 27, p. 5039 - 5045]

5
[ 918959-32-7 ]
[ 600727-96-6 ]

Yield	Reaction Conditions	Operation in experiment
72.1%	Stage #1: 2,6-di-pyrazol-1-yl-isonicotinic acid methyl ester With potassium hydroxide In water Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water at 20℃; for 1h;
	With lithium hydroxide In tetrahydrofuran

Reference： [1]Kumar, Kuppusamy Senthil; Šalitroš, Ivan; Moreno-Pineda, Eufemio; Ruben, Mario [Dalton Transactions, 2017, vol. 46, # 30, p. 9765 - 9768]
[2]Location in patent: scheme or table Basak, Supratim; Hui, Pramiti; Chandrasekar, Rajadurai [Synthesis, 2009, # 23, p. 4042 - 4048]

6
[ 600727-96-6 ]
[ 918959-35-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; oxalyl dichloride; potassium carbonate; trifluoroacetic acid

Reference： [1]Location in patent: scheme or table Basak, Supratim; Hui, Pramiti; Chandrasekar, Rajadurai [Synthesis, 2009, # 23, p. 4042 - 4048]

7
[ 288-13-1 ]
[ 5398-44-7 ]
[ 1152836-87-7 ]
[ 600727-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 60℃; Inert atmosphere; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 60℃; for 24h; Inert atmosphere;	2.2. General procedure for the synthesis of 6a-7a and 7b General procedure: To a suspension of NaH (55-65% in mineral oil, 1.1 g, ≈25 mmol) in anhydrous DMF (40 ml) was dropwise added a solution of 3a or 3b (21 mmol) in anhydrous DMF (10 ml) at room temperature and under argon. The resulting slurry was heated to 60 °C for 45 min and compound 2 (2 g, 10 mmol) was added in one portion. The brown mixture was then heated to 60 °C under argon for 24 h. DMF was evaporated and water (100 ml) was added. The mixture was acidified with concd HCl and the formed precipitate was filtered and washed with water. The solid was dissolved in EtOAc, dried over MgSO4 and evaporated to afford crude mixtures of compounds 4a-5a (1.4 g) or 4b-5b (1.65 g) as slightly brown solids. Crude mixture of 4a-5a or 4b-5b was refluxed overnight in 75 ml of EtOH and 2 ml of concd H2SO4. After being cooled to room temperature, EtOH was evaporated and the resulting residue was dissolved in CH2Cl2 (150 ml), successively washed with saturated NaHCO3 solution (2 × 100 ml), water (100 ml), dried over MgSO4 and finally evaporated to dryness. Purifications were performed as follows:Compound 6a-7a: the resulting brown solid was dissolved in the minimum volume of CH2Cl2 and hexane (100 ml) was added. The insoluble brown impurities were filtered off and the clear filtrate was evaporated to afford 1.4 g of a mixture composed of disubstituted 6a and monosubstituted 7a compound in a 1:6 ratio according to the 1H NMR.Compound 6b-7b: the resulting brown solid was dissolved in the minimum volume of CH2Cl2 and purified by column chromatography (SiO2, CH2Cl2) to afford 1.5 g (54%) of pure 7b as a white solid (first band). 1H NMR (200 MHz, 25 °C, CDCl3) δ 1.43 (t, J = 7 Hz, 3H), 2.31 (s, 3H), 2.67 (s, 3H), 4.44 (q, J = 7 Hz, 2H), 6.02 (s, 1H), 7.68 (s, 1H), 8.35 (s, 1H).

Reference： [1]Location in patent: experimental part Klein, Cédric; Baranoff, Etienne; Grätzel, Michael; Nazeeruddin, Md. Khaja [Tetrahedron Letters, 2011, vol. 52, # 5, p. 584 - 587]

8
[ 288-13-1 ]
[ 5398-44-7 ]
[ 600727-96-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20 - 100℃; Inert atmosphere; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 130℃; for 72h; Inert atmosphere;	2.1. General procedure for the synthesis of 4a and 4b General procedure: To a suspension of NaH (55-65% in mineral oil, 1.31 g, ≈30 mmol) in anhydrous DMF (30 ml) was dropwise added a solution of 3a or 3b (30 mmol) in anhydrous DMF (10 ml) at room temperature and under argon. The resulting slurry was heated to 100 °C for 45 min and compound 2 (1 g, 5.21 mmol) was added in one portion. The brown mixture was then heated to 130 °C under argon for three days. DMF was evaporated and water (100 ml) was added. The mixture was acidified with concd HCl and the formed precipitate was filtered and washed with water. The solid was dissolved in the minimum volume of hot acetone and let to stand overnight in the freezer. Compounds 4a and 4b were, respectively, obtained after filtration and washing with cold portions of acetone (3 × 5 ml).Compound 4a: 1.06 g, yield = 80%, white solid. 1H and 13C NMR were in accordance with those already reported.18Compound 4b: 1.16 g, yield = 71%, white solid. 1H NMR (200 MHz, 25 °C, DMSO-d6) δ 2.22 (s, 6H), 2.57 (s, 6H), 6.16 (s, 2H), 8.05 (s, 2H). 13C NMR (50 MHz, 25 °C, DMSO-d6) δ 13.7, 14.2, 109.9, 112.5, 141.2, 143.4, 150.3, 152.2, 165.5.
71%	With potassium hydride In N,N-dimethyl-formamide at 130℃; for 120h; Inert atmosphere;
68.3%	Stage #1: NH-pyrazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 100℃; for 1h; Stage #2: 2,6-dichloropyridine-4-carboxylic acid In N,N-dimethyl-formamide; mineral oil at 130℃; for 120h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Klein, Cédric; Baranoff, Etienne; Grätzel, Michael; Nazeeruddin, Md. Khaja [Tetrahedron Letters, 2011, vol. 52, # 5, p. 584 - 587]
[2]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Blundell, Toby J.; Le Maguere, Pierre; Turner, Scott S. [Dalton Transactions, 2021, vol. 50, # 34, p. 11843 - 11851]
[3]Meier, Dennis; Adak, Abhishek K.; Knecht, Peter; Reichert, Joachim; Mondal, Sourav; Suryadevara, Nithin; Kuppusamy, Senthil Kumar; Eguchi, Keitaro; Muntwiler, Matthias K.; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Narasimhan, Shobhana; Papageorgiou, Anthoula C. [Angewandte Chemie - International Edition, 2021, vol. 60, # 52, p. 26932 - 26938][Angew. Chem., 2021, vol. 133, # 52, p. 27138 - 27144]

9
[ 99-11-6 ]
[ 1152836-87-7 ]
[ 600727-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / 24 h / 140 °C 1.2: 2 h / 0 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 60 °C / Inert atmosphere 2.2: 24 h / 60 °C / Inert atmosphere

Reference： [1]Klein, Cédric; Baranoff, Etienne; Grätzel, Michael; Nazeeruddin, Md. Khaja [Tetrahedron Letters, 2011, vol. 52, # 5, p. 584 - 587]

10
[ 99-11-6 ]
[ 600727-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / 24 h / 140 °C 1.2: 2 h / 0 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 - 100 °C / Inert atmosphere 2.2: 72 h / 130 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: tetramethlyammonium chloride; trichlorophosphate / 140 °C / Inert atmosphere 2.1: sodium hydride / diethylene glycol dimethyl ether / 1 h 2.2: 120 h / 140 °C
	Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate / neat (no solvent) / 24 h / 140 °C / Reflux 2: potassium hydride / N,N-dimethyl-formamide / 120 h / 130 °C / Inert atmosphere

Reference： [1]Klein, Cédric; Baranoff, Etienne; Grätzel, Michael; Nazeeruddin, Md. Khaja [Tetrahedron Letters, 2011, vol. 52, # 5, p. 584 - 587]
[2]Bridonneau, Nathalie; Rigamonti, Luca; Poneti, Giordano; Pinkowicz, Dawid; Forni, Alessandra; Cornia, Andrea [Dalton Transactions, 2017, vol. 46, # 12, p. 4075 - 4085]
[3]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Blundell, Toby J.; Le Maguere, Pierre; Turner, Scott S. [Dalton Transactions, 2021, vol. 50, # 34, p. 11843 - 11851]

11
iron(II) perchlorate hydrate [ No CAS ]
[ 600727-96-6 ]
[Fe(2,6-bis(1H-pyrazol-1-yl)isonicotinic acid)₂](ClO₄)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone for 0.25h;

Reference： [1]Abherve, Alexandre; Clemente-Leon, Miguel; Coronado, Eugenio; Gomez-Garcia, Carlos J.; Lopez-Jorda, Maurici [Dalton Transactions, 2014, vol. 43, # 25, p. 9406 - 9409]

12
[ 288-13-1 ]
[ 42521-09-5 ]
[ 600727-96-6 ]

Reference： [1]Dalton Transactions,2017,vol. 46,p. 4075 - 4085

13
[ 67-56-1 ]
[ 600727-96-6 ]
[ 918959-32-7 ]

Yield	Reaction Conditions	Operation in experiment
82.3%	With thionyl chloride at 20℃; for 5h; Inert atmosphere;

Reference： [1]Bridonneau, Nathalie; Rigamonti, Luca; Poneti, Giordano; Pinkowicz, Dawid; Forni, Alessandra; Cornia, Andrea [Dalton Transactions, 2017, vol. 46, # 12, p. 4075 - 4085]

14
[ 67000-89-9 ]
[ 600727-96-6 ]
2,6-d-pyrazol-1-yl-isonicotinic acid 4-pyren-1-yl-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere; Schlenk technique;

Reference： [1]Kumar, Kuppusamy Senthil; Šalitroš, Ivan; Moreno-Pineda, Eufemio; Ruben, Mario [Dalton Transactions, 2017, vol. 46, # 30, p. 9765 - 9768]

15
[ 119308-57-5 ]
[ 600727-96-6 ]

Reference： [1]Dalton Transactions,2017,vol. 46,p. 9765 - 9768

16
cobalt(II) perchlorate hydrate [ No CAS ]
iron(II) perchlorate hydrate [ No CAS ]
[ 600727-96-6 ]
0.92Fe⁽²⁺⁾*0.08Co⁽²⁺⁾*2C₁₂H₉N₅O₂*2ClO₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone for 0.25h;	2 2.1.2 [Fe^II_0.92Co^II_0.08(bppCOOH)₂](ClO₄)₂ 4mL of a solution of 13 Fe(ClO4)2·xH2O (57.3mg in 10mL 10 acetone) and 0.5mL of a solution of 9 Co(ClO4)2·xH2O (82.3mg in 10mL acetone) were added to a solution of bppCOOH (76.8mg, 0.269mmol) in acetone (20mL) and the mixture was stirred for 15min. A red/orange solution was formed. An orange 14 powder was obtained by slow addition of 40mL of diethyl ether into this solution. Microanalysis shows a Co:Fe and Metal:Cl ratios close to 8.1:91.9 and 1:2, respectively (see ESI: Fig. 8S). Anal. Calc. for [FeII0.92CoII0.08(bppCOOH)2](ClO4)2·H2O: C, 36.79; H, 2.57; N, 17.88. Found: C, 36.37; H, 2.68; N, 17.36%.

Reference： [1]García-López; Orts-Mula; Palacios-Corella; Clemente-Juan; Clemente-León; Coronado [Polyhedron, 2018, vol. 150, p. 54 - 60]

17
cobalt(II) perchlorate hydrate [ No CAS ]
[ 67-64-1 ]
[ 600727-96-6 ]
C₂₄H₁₈CoN₁₀O₄⁽²⁺⁾*2ClO₄^(1-)*2C₃H₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	for 0.25h;	2.1.1 [Co^II(bppCOOH)₂](ClO₄)₂·2Me₂CO A solution of Co(ClO4)2·xH2O (18.3mg, 0.05mmol) in acetone (1.5mL) was added to a solution of bppCOOH (28.5mg, 0.10mmol) in acetone (1.5mL) and the mixture was stirred for 15min. An orange solution was formed. Red/orange prismatic crystals of [CoII(bppCOOH)2](ClO4)2·2Me2CO suitable for X-ray diffraction were obtained by slow diffusion of diethyl ether into this solution. These crystals lose crystallinity after extracting the crystals from the mother liquor. Due to this they change composition with respect to the structure solved at 120K (see below). Microanalysis shows a Co:Cl ratio close to 1:2. Anal. Calc. for [CoII(bppCOOH)2](ClO4)2·H2O: C, 36.66; H, 2.56; N, 17.81. Found: C, 37.02; H, 2.54; N, 17.64%.

Reference： [1]García-López; Orts-Mula; Palacios-Corella; Clemente-Juan; Clemente-León; Coronado [Polyhedron, 2018, vol. 150, p. 54 - 60]

18
[ 600727-96-6 ]
4-methoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 12 h / Reflux; Inert atmosphere 2: triethylamine / 48 h / 20 °C

Reference： [1]Galadzhun, Iurii; Kulmaczewski, Rafal; Cespedes, Oscar; Yamada, Mihoko; Yoshinari, Nobuto; Konno, Takumi; Halcrow, Malcolm A. [Inorganic Chemistry, 2018, vol. 57, # 21, p. 13761 - 13771]

19
[ 600727-96-6 ]
4-hydroxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / 12 h / Reflux; Inert atmosphere 2: triethylamine / 48 h / 20 °C 3: boron tribromide / dichloromethane / 4 h / -70 °C / Inert atmosphere; Reflux

20
[ 600727-96-6 ]
[2,6-di(pyrazol-1-yl)pyrid-4-yl]carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride for 12h; Reflux; Inert atmosphere;

21
[ 18979-55-0 ]
[ 600727-96-6 ]
4-hexoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

22
[ 13037-87-1 ]
[ 600727-96-6 ]
4-dodecoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

23
[ 13224-40-3 ]
[ 600727-96-6 ]
4-tetradecoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

24
[ 13037-88-2 ]
[ 600727-96-6 ]
4-hexadecoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

25
[ 67399-92-2 ]
[ 600727-96-6 ]
4-octadecoxyphenyl [2,6-di(pyrazol-1-yl)pyrid-4-yl]carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

26
[ 600727-96-6 ]
[ 111-27-3 ]
hexyl 2,6-di(pyrazol-1-yl)pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

27
[ 112-53-8 ]
[ 600727-96-6 ]
dodecyl 2,6-di(pyrazol-1-yl)pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

28
[ 112-72-1 ]
[ 600727-96-6 ]
tetradecyl 2,6-di(pyrazol-1-yl)pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

29
[ 36653-82-4 ]
[ 600727-96-6 ]
hexadecyl 2,6-di(pyrazol-1-yl)pyridine-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 48h;

30
iron(II) tetrafluoroborate hexahydrate [ No CAS ]
[ 600727-96-6 ]
C₂₄H₁₈FeN₁₀O₄⁽²⁺⁾*2BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone for 0.25h; Inert atmosphere; Glovebox;

Reference： [1]Garciá-López, Víctor; Palacios-Corella, Mario; Abhervé, Alexandre; Pellicer-Carrenõ, Isaac; Desplanches, Cédric; Clemente-León, Miguel; Coronado, Eugenio [Dalton Transactions, 2018, vol. 47, # 47, p. 16958 - 16968]

31
[ 24463-15-8 ]
[ 600727-96-6 ]
2,6-di-pyrazol-1-yl-isonicotinic acid pyren-1-yl-methylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Kumar, Kuppusamy Senthil; Šalitroš, Ivan; Suryadevara, Nithin; Moreno-Pineda, Eufemio; Ruben, Mario [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 47, p. 5091 - 5097]

32
[ 600727-96-6 ]
2,6-bis(pyrazol-1-yl)pyridine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Stage #2: With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 2h; Sealed tube;
88%	Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Reflux; Stage #2: With ammonium hydroxide In tetrahydrofuran; water for 2h;

Reference： [1]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Cruickshank, Dyanne; Turner, Scott S. [Dalton Transactions, 2019, vol. 48, # 1, p. 90 - 98]
[2]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Blundell, Toby J.; Le Maguere, Pierre; Turner, Scott S. [Dalton Transactions, 2021, vol. 50, # 34, p. 11843 - 11851]

33
[ 600727-96-6 ]
2,6-bis(pyrazol-1-yl)pyridine-4-carbothioamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride / 4 h / 75 °C 1.2: 2 h / 20 °C / Sealed tube 2.1: Lawesson’s reagent / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Cruickshank, Dyanne; Turner, Scott S. [Dalton Transactions, 2019, vol. 48, # 1, p. 90 - 98]

34
[ 74-89-5 ]
[ 600727-96-6 ]
C₁₃H₁₂N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 2,6-bis(pyrazole-1-yl)pyridine-4-carboxylic acid With thionyl chloride at 75℃; for 4h; Stage #2: methylamine In tetrahydrofuran; ethanol at 20℃; for 2h; Sealed tube;

Reference： [1]Attwood, Max; Akutsu, Hiroki; Martin, Lee; Cruickshank, Dyanne; Turner, Scott S. [Dalton Transactions, 2019, vol. 48, # 1, p. 90 - 98]

35
zinc(II) nitrate hexahydrate [ No CAS ]
[ 600727-96-6 ]
Zn(2,6-bis(pyrazol-1-yl)pyridine-4-carboxylate)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydroxide In water; N,N-dimethyl-formamide at 120℃; for 60h; High pressure;

Reference： [1]Bommakanti, Suresh; Venkataramudu, Uppari; Das, Samar K. [Crystal Growth and Design, 2019, vol. 19, # 2, p. 1155 - 1166]

36
cobalt(II) chloride hexahydrate [ No CAS ]
[ 7732-18-5 ]
[ 600727-96-6 ]
{Co(2,6-bis(pyrazol-1-yl)pyridine-4-carboxylate)(HCOO)(H₂O)}n*n1.5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In N,N-dimethyl-formamide at 120℃; for 60h; High pressure;

Reference： [1]Bommakanti, Suresh; Venkataramudu, Uppari; Das, Samar K. [Crystal Growth and Design, 2019, vol. 19, # 2, p. 1155 - 1166]

37
[ 67-56-1 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 600727-96-6 ]
C₂₆H₂₄MnN₁₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With triethylamine at 70℃; for 0.166667h;

Reference： [1]Uchida, Kaiji; Cosquer, Goulven; Sugisaki, Kenji; Matsuoka, Hideto; Sato, Kazunobu; Breedlove, Brian K.; Yamashita, Masahiro [Dalton Transactions, 2019, vol. 48, # 32, p. 12023 - 12030]

38
[ 67-56-1 ]
iron(II) chloride tetrahydrate [ No CAS ]
[ 600727-96-6 ]
C₂₆H₂₄FeN₁₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine at 70℃; for 0.166667h;

39
[ 67-56-1 ]
[ 7646-79-9 ]
[ 600727-96-6 ]
C₂₆H₂₄CoN₁₀O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With triethylamine at 70℃; for 0.166667h;

40
[ 600727-96-6 ]
lithium 2,6-bis(1H-pyrazol-1-yl)isonicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide In methanol for 1h; Reflux;

Reference： [1]Moreau, Florian; Marrot, Jérôme; Banse, Frédéric; Serre, Christian; Tissot, Antoine [Journal of Materials Chemistry C, 2020, vol. 8, # 47, p. 16826 - 16833]

41
iron(II) perchlorate hydrate [ No CAS ]
Zn₅(bis(1H-1,2,3-triazolo[4,5-b],-[4',5'-i])dibenzo[1,4]dioxin)₃(2,6-bis(1H-pyrazol-1-yl)isonicotinate)₂Cl₂ [ No CAS ]
[ 600727-96-6 ]
Zn₅(bis(1H-1,2,3-triazolo[4,5-b],-[4',5'-i])dibenzo[1,4]dioxin)₃Cl₂[(2,6-bis(1H-pyrazol-1-yl)isonicotinate)₂Fe₂(2,6-bis(1H-pyrazol-1-yl)isonicotinic acid)_1.5(ClO₄)₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol for 16h;

Reference： [1]Moreau, Florian; Marrot, Jérôme; Banse, Frédéric; Serre, Christian; Tissot, Antoine [Journal of Materials Chemistry C, 2020, vol. 8, # 47, p. 16826 - 16833]

42
iron(II) perchlorate hydrate [ No CAS ]
Al3O(OH)0.4(H2O)2(benzene-1,3,5-tricarboxylate)2(2,6-bis(1H-pyrazol-1-yl)isonicotinate)0.6 [ No CAS ]
[ 600727-96-6 ]
[Al_2.₆₇Fe_0.₃₃O(OH)_0.4(H₂O)₂(benzene-1,3,5-tricarboxylate)₂][(2,6-bis(1H-pyrazol-1-yl)isonicotinate)_0.6Fe_0.6(2,6-bis(1H-pyrazol-1-yl)isonicotinic acid)_0.5₁(ClO₄)_1.2] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol for 16h;

Reference： [1]Moreau, Florian; Marrot, Jérôme; Banse, Frédéric; Serre, Christian; Tissot, Antoine [Journal of Materials Chemistry C, 2020, vol. 8, # 47, p. 16826 - 16833]

43
[ 600727-96-6 ]
2-[(2,6-di(pyrazol-1-yl)pyridine)-4-carboxamido]acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C