[ CAS No. 75055-73-1 ]

Name: 75055-73-1|1-(Pyridin-4-yl)butane-1,3-dione|98%
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Quality Control of [ 75055-73-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 75055-73-1 ]

CAS No. :	75055-73-1	MDL No. :	MFCD07438022
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BZZPMCZQQJWNTB-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	12418330
Synonyms :

Safety of [ 75055-73-1 ]

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

Application In Synthesis of [ 75055-73-1 ]

* 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 [ 75055-73-1 ]

[ 75055-73-1 ] Synthesis Path-Downstream 1~50

1
[ 75055-73-1 ]
[ 39943-64-1 ]
[ 131197-02-9 ]
[ 131197-01-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Wright et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 5637,5639,5640]

2
[ 75055-73-1 ]
[ 5446-16-2 ]
[ 131197-00-7 ]
[ 131196-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Wright et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 5637,5639,5640]

3
[ 75055-73-1 ]
[ 15384-39-1 ]
4-[2-(3-methoxy-phenyl)-5-methyl-2<i>H</i>-pyrazol-3-yl]-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol

Reference： [1]Wright et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 5637,5639,5640]

4
[ 75055-73-1 ]
[ 14763-20-3 ]
[ 107915-27-5 ]
[ 107915-26-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Wright et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 5637,5639,5640]

5
[ 75055-73-1 ]
[ 20242-40-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium carbonate In ethanol
	With hydroxylamine hydrochloride In methanol; water for 2h; Heating;

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]
[2]Belgodere, Elena; Bossio, Ricardo; Sio, Francesco De; Marcaccini, Stefano; Pepino, Roberto [Heterocycles, 1983, vol. 20, # 3, p. 501 - 504]

6
[ 75055-73-1 ]
[ 3594-40-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; SULFAMIDE In ethanol

Reference： [1]Wright,J.B. [Journal of Organic Chemistry, 1964, vol. 29, p. 1905 - 1909]

7
[ 2459-09-8 ]
[ 67-64-1 ]
[ 75055-73-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: 4-pyridinecarboxylic acid, methyl ester; acetone With sodium methylate In diethyl ether for 6h; Heating / reflux; Stage #2: With water; acetic acid	OO-1.1 Stepi: 1-Pyridin-4-ylbutane-1, 3-dione (oo-1); To a 500 mL flask with NaOMe (4.75 g) and anhydrous ether (130 mL) was sequentially added methyl isonicotinate (10.0 mL, 84.7 mmol), and a solution of acetone (12.4 mmol, 169 mmol) in ether {45 mL). The suspension was stirred at reflux for 6 hours, cooled, and filtered. The isolated solid was washed with ether and dissolved in water (40 mL). Glacial acetic acid (5.2 mL) was added and the mixture was extracted with chloroform (40 mL x 2). The organic extracts were dried over anhydrous Na2SO4 and concentrated to give the title compound oo-1 (8.6 g, 62% yield) as a brown solid, which was used without further purification. LCMS: 164.10 [M + H+]
60%	With sodium methylate In tetrahydrofuran 1.) RT, 30 min, 2.) reflux, 2.5 h;

Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/17932, 2008, A2 Location in patent: Page/Page column 92
[2]Singh, Baldev; Lesher, George Y.; Pluncket, Kevin C.; Pagani, Edward D.; Bode, Donald C.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 26, p. 4858 - 4865]

8
[ 75055-73-1 ]
[ 7357-70-2 ]
[ 109658-32-4 ]
[ 119934-17-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 10% 2: 86%	With TEA In ethanol for 0.75h; Heating;

Reference： [1]Hahfeld, Vera; Leistner, S.; Wagner, G. [Pharmazie, 1988, vol. 43, # 11, p. 762 - 764]

9
[ 75055-73-1 ]
[ 14337-43-0 ]
[ 134842-96-9 ]

Yield	Reaction Conditions	Operation in experiment
76.5%	With sodium ethanolate In ethanol

Reference： [1]Dal Piaz; Ciciani; Turco; Giovannoni; Miceli; Pirisino; Perretti [Journal of Pharmaceutical Sciences, 1991, vol. 80, # 4, p. 341 - 348]

10
[ 75055-73-1 ]
[ 107-91-5 ]
[ 118803-97-7 ]
[ 118803-96-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 24%	With TEA In ethanol for 0.666667h; Heating;

Reference： [1]Hahfeld, Vera; Leistner, S.; Wagner, G. [Pharmazie, 1988, vol. 43, # 11, p. 762 - 764]

11
[ 75055-73-1 ]
[ 35250-71-6 ]

Yield	Reaction Conditions	Operation in experiment
62.7%	With formic acid; zinc for 6.5h; Heating;

Reference： [1]Ferles, Miloslav; Kafka, Stanislav; Silhankova, Alexandra; Sputova, Michaela [Collection of Czechoslovak Chemical Communications, 1981, vol. 46, # 5, p. 1167 - 1172]

12
[ 75055-73-1 ]
4-Bromo-1-pyridin-4-yl-butane-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In chloroform for 24h;

Reference： [1]Hablouj; Robert; Panouse; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 6, p. 499 - 504]

13
6-hydrazineylpyridine-3-sulfonamide [ No CAS ]
[ 75055-73-1 ]
[ 1006908-09-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 6-hydrazineylpyridine-3-sulfonamide; 1-(4-pyridyl)-1,3-butanedione With acetic acid at 110℃; for 1h; Stage #2: With water; sodium hydrogencarbonate	OO-1.2 Step 2: 6-{3-Methyl-5-pyridin-4-yl-1 H-pyrazol-1-yl)pyridine-3-sulfonamide (OO-1 ); To 1-pyridin-4-ylbutane-1,3-dione 21-1 (245 mg, 1.50 mmol) in 1.5 mL of acetic acid was added6-hydrazinopyridine-3-sulfonamide {282 mg, 1.5 mmol). The mixture was heated at 11O0C for one hour and cooled, then basified to pH 7 with Sat. NaHCO3. The resultant solid was filtered, washed with water and hexane/ether (1 :1), then dried under vacuum to give the title compound U-1 (349 mg, yield 74%) as a light brown solid. Regiochemistry assumed from similar spectral data to compounds for literature, see

Reference： [1]Current Patent Assignee: PFIZER INC - WO2008/17932, 2008, A2 Location in patent: Page/Page column 93

14
[ 75055-73-1 ]
[ 119934-18-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 86 percent / TEA / ethanol / 0.75 h / Heating 2: 71 percent / NaOC₂H₅ / ethanol / 2 h / Heating

Reference： [1]Hahfeld, Vera; Leistner, S.; Wagner, G. [Pharmazie, 1988, vol. 43, # 11, p. 762 - 764]

15
[ 75055-73-1 ]
5-(4-pyridinyl)-1,6-naphthyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2.) NaH / 1.) 1,4-dioxane, overnight, 2.) DMF, reflux, 3.5 h 2: 2.) NH₄OAc / 1.) DMF, reflux, 5 h, 2.) DMF, reflux, 5 h 3: 88 percent / aq. NaOH / 6 h / Heating 4: 72 percent / 0.05 h / 370 - 375 °C

Reference： [1]Singh, Baldev; Lesher, George Y.; Pluncket, Kevin C.; Pagani, Edward D.; Bode, Donald C.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 26, p. 4858 - 4865]

16
[ 75055-73-1 ]
[ 102995-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 2.) NaH / 1.) 1,4-dioxane, overnight, 2.) DMF, reflux, 3.5 h 2: 2.) NH₄OAc / 1.) DMF, reflux, 5 h, 2.) DMF, reflux, 5 h

Reference： [1]Singh, Baldev; Lesher, George Y.; Pluncket, Kevin C.; Pagani, Edward D.; Bode, Donald C.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 26, p. 4858 - 4865]

17
[ 75055-73-1 ]
[ 102995-79-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 2.) NaH / 1.) 1,4-dioxane, overnight, 2.) DMF, reflux, 3.5 h 2: 2.) NH₄OAc / 1.) DMF, reflux, 5 h, 2.) DMF, reflux, 5 h 3: 88 percent / aq. NaOH / 6 h / Heating

Reference： [1]Singh, Baldev; Lesher, George Y.; Pluncket, Kevin C.; Pagani, Edward D.; Bode, Donald C.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 26, p. 4858 - 4865]

18
[ 75055-73-1 ]
[ 107504-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromine / CHCl₃ / 24 h 2: acetone / 24 h 3: 70 percent / ammonium hydroxyde / H₂O; CHCl₃

Reference： [1]Hablouj; Robert; Panouse; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 6, p. 499 - 504]

19
[ 75055-73-1 ]
[ 107504-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bromine / CHCl₃ / 24 h 2: acetone / 24 h

Reference： [1]Hablouj; Robert; Panouse; et al. [European Journal of Medicinal Chemistry, 1986, vol. 21, # 6, p. 499 - 504]

20
[ 75055-73-1 ]
[ 134843-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76.5 percent / NaOEt / ethanol 2: 70 percent / hydrazine / ethanol / 2 h 3: 73 percent / H₂ / 10percent Pd/C / ethanol / 12 h

Reference： [1]Dal Piaz; Ciciani; Turco; Giovannoni; Miceli; Pirisino; Perretti [Journal of Pharmaceutical Sciences, 1991, vol. 80, # 4, p. 341 - 348]

21
[ 75055-73-1 ]
[ 134842-97-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76.5 percent / NaOEt / ethanol 2: 70 percent / hydrazine / ethanol / 2 h

Reference： [1]Dal Piaz; Ciciani; Turco; Giovannoni; Miceli; Pirisino; Perretti [Journal of Pharmaceutical Sciences, 1991, vol. 80, # 4, p. 341 - 348]

22
[ 75055-73-1 ]
[ 134859-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76.5 percent / NaOEt / ethanol 2: 86 percent / ethanol / 2 h

Reference： [1]Dal Piaz; Ciciani; Turco; Giovannoni; Miceli; Pirisino; Perretti [Journal of Pharmaceutical Sciences, 1991, vol. 80, # 4, p. 341 - 348]

23
[ 75055-73-1 ]
[ 134843-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76.5 percent / NaOEt / ethanol 2: 86 percent / ethanol / 2 h 3: 68 percent / H₂ / 10percent Pd/C / ethanol / 12 h

Reference： [1]Dal Piaz; Ciciani; Turco; Giovannoni; Miceli; Pirisino; Perretti [Journal of Pharmaceutical Sciences, 1991, vol. 80, # 4, p. 341 - 348]

24
[ 75055-73-1 ]
[ 111562-64-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol 2: aqueous HBr

Reference： [1]Wright et al. [Journal of the American Chemical Society, 1959, vol. 81, p. 5637,5639,5640]

25
[ 75055-73-1 ]
[ 20242-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NH₂OH*HCl, Na₂CO₃ / aq. ethanol

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]

26
[ 75055-73-1 ]
[ 20242-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NH₂OH*HCl, Na₂CO₃ / aq. ethanol

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]

27
[ 75055-73-1 ]
[ 20242-36-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NH₂OH*HCl, Na₂CO₃ / aq. ethanol

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]

28
[ 75055-73-1 ]
[ 18704-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NH₂OH*HCl, Na₂CO₃ / aq. ethanol

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]

29
[ 75055-73-1 ]
[ 18704-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NH₂OH*HCl, Na₂CO₃ / aq. ethanol

Reference： [1]Bauer,V.J. et al. [Journal of Medicinal Chemistry, 1968, vol. 11, # 5, p. 984 - 986]

30
[ 75055-73-1 ]
[ 102292-32-0 ]
5-methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; acetic acid	58 5-Methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile EXAMPLE 58 5-Methyl-2-[4-(phenylmethyl)-1-piperazinyl]-7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile A mixture of 4.8 g (0.03 moles) of 1-(4-pyridyl)-1,3-butanedione [J. Chem. Soc. (1950) p 1680], 8.4 g (0.03 moles) of 3-amino-5-(4-phenylmethyl-1-piperazinyl)-4-pyrazolecarbonitrile (prepared as described in Example 1) and 100 ml of glacial acetic acid was stirred at reflux for 18 hours. The resulting solution was evaporated in vacuo and gave an oil. The residue was partitioned between 100 ml of saturated sodium bicarbonate and 200 ml of dichloromethane. The organic layer was separated, dried over magnesium sulfate and passed through a short column of magnesium silicate. The elude was heated to boiling on a steam bath and 200 ml of hexane was added. The solution was concentrated by heating until a precipitate began to form. The mixture was then cooled at -10° C. and filtered. The precipitate was washed with hexane. The filtrate and wash was combined, concentrated to turbidity, cooled at -10° C. and filtered to collect the solid which was dried and gave 3.9 g of the desired product as a yellow solid, mp 179°-180° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4576943, 1986, A

31
[ 75055-73-1 ]
2-Bromo-2-(pyridin-4-yl)-1,3-butadione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In hydrogen bromide	5.A A. A. 2-Bromo-2-(4-pyridyl)-1,3-butadione To a solution of 16.3 g (0.1 mole) of 1-(4-pyridyl)-1,3-butadione in 100 ml, 48% hydrobromic acid is slowly added 15.98 g (0.1 mol) bromine. The solution is stirred until the bromine color is discharged. The solution is evaporated to dryness to give the title compound.

Reference： [1]Current Patent Assignee: SANOFI - US4866182, 1989, A

32
[ 75055-73-1 ]
beryllium(II) sulphate tetrahydrate [ No CAS ]
[ 858861-93-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With pyridine In methanol; water aq. soln. of Be sulfate added slowly to soln. of diketone and small amt.of pyridine in MeOH; ppt. filtered off and washed with water, recrystd, from 2-PrOH/CHCl3;

Reference： [1]Vreshch, Volodimir D.; Lysenko, Andrey B.; Chernega, Alexander N.; Sieler, Joachim; Domasevitch, Konstantin V. [Polyhedron, 2005, vol. 24, # 8, p. 917 - 926]

33
[ 75055-73-1 ]
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] [ No CAS ]
[ 2923-28-6 ]
[(η5-pentamethylcyclopentadienyl)Ir(1-(4-pyridinyl)butane-1,3-dionato)]4(triflate)4 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	In methanol byproducts: AgCl; under N2; mixt. of Ir complex and AgSO3CF3 in MeOH stirred at room temp.for 3 h; filtered; ligand added to filtrate; stirred for 12 h; solvent removed under reduced pressure; extd. with CH2Cl2; residue solidrecrystd. from CH2Cl2-Et2O; elem. anal.;

Reference： [1]Wang, Guo-Liang; Lin, Yue-Jian; Berke, Heinz; Jin, Guo-Xin [Inorganic Chemistry, 2010, vol. 49, # 5, p. 2193 - 2201]

34
gallium(III) nitrate [ No CAS ]
[ 75055-73-1 ]
[ 1263416-25-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	With NaHCO₃ In methanol; water addn. of NaHCO3 to soln. of gallium compd. and diketone deriv. in methanol/water (1:1), stirring at room temp. for 4 h; filtration, dissolving in CH2Cl2, washing with water, drying over Na2SO4, filtration, evapn., addn. of ethyl acetate and hexane (1:1), filtration, elem. anal.;

Reference： [1]Wang, Ming; Vajpayee, Vaishali; Shanmugaraju, Sankarasekaran; Zheng, Yao-Rong; Zhao, Zhigang; Kim, Hyunuk; Mukherjee, Partha Sarathi; Chi, Ki-Whan; Stang, Peter J. [Inorganic Chemistry, 2011, vol. 50, # 4, p. 1506 - 1512]

35
[ 75055-73-1 ]
C₂₈H₂₉N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0 °C 1.2: 20 °C 2.1: acetic acid / 20 °C
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0 °C 1.2: 20 °C 2.1: hydrazine hydrate / acetic acid / 20 °C 3.1: Alkaline conditions

Reference： [1]Andrés, Miriam; Bravo, Mónica; Buil, Maria Antonia; Calbet, Marta; Castro, Jordi; Domènech, Teresa; Eichhorn, Peter; Ferrer, Manel; Gómez, Elena; Lehner, Martin D.; Moreno, Imma; Roberts, Richard S.; Sevilla, Sara [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3349 - 3353]
[2]Andrés, Miriam; Bravo, Mónica; Buil, Maria Antonia; Calbet, Marta; Castro, Jordi; Domènech, Teresa; Eichhorn, Peter; Ferrer, Manel; Gómez, Elena; Lehner, Martin D.; Moreno, Imma; Roberts, Richard S.; Sevilla, Sara [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 11, p. 3349 - 3353]

36
[ 75055-73-1 ]
C₂₈H₂₇F₂N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0 °C 1.2: 20 °C 2.1: acetic acid / 20 °C
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0 °C 1.2: 20 °C 2.1: hydrazine hydrate / acetic acid / 20 °C 3.1: Alkaline conditions

37
[ 75055-73-1 ]
[ 5292-43-3 ]
C₁₅H₁₉NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-(4-pyridyl)-1,3-butanedione With sodium hydride In tetrahydrofuran at 0℃; Stage #2: bromoacetic acid <i>tert</i>-butyl ester In tetrahydrofuran at 20℃;

38
[ 75055-73-1 ]
[ 105510-34-7 ]
C₂₂H₁₉NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-(4-pyridyl)-1,3-butanedione With sodium hydride In tetrahydrofuran; hexane; mineral oil at 20℃; for 1h; Cooling with ice; Stage #2: 1-(bromomethyl)-2-(phenylsulfonyl)benzene In tetrahydrofuran; hexane; mineral oil at 20℃; for 18h;	5.2.1. 1-Phenyl-2-[2-(phenylsulfonyl)benzyl]butane-1,3-dione (24) General procedure: Sodium hydride (60% dispersion in oil, 118 mg, 2.95 mmol) was first washed with hexanes to remove the oil and was then suspended in 10 ml tetrahydrofuran and cooled to 0°C in an ice-bath. A solution of 1-phenylbutane-1,3-dione 23 (300 mg, 1.85 mmol) dissolved in 2 ml tetrahydrofuran was added drop-wise and with stirring. Upon addition, the mixture was stirred for 1 h at room temperature. A solution of 1-(bromomethyl)-2-(phenylsulfonyl)benzene (22) (690 mg, 2.22 mmol) in 3 ml tetrahydrofuran wasadded drop-wise with stirring and the mixture was stirred overnightat room temperature. The organics were concentrated underreduced pressure and the residue was re-suspended in aqueousammonium chloride solution. The solution was extracted threetimes with ether and the combined organics were washed withbrine, dried over sodium sulphate and evaporated under reducedpressure. The residue was purified by reverse-phase chromatographyusing the SP1 Purification System to give 24 (256 mg,0.65 mmol, 35%) as a colourless oil. Purity 94%.

Reference： [1]Andrés, Miriam; Bravo, Mónica; Buil, Maria Antonia; Calbet, Marta; Castillo, Marcos; Castro, Jordi; Eichhorn, Peter; Ferrer, Manel; Lehner, Martin D.; Moreno, Imma; Roberts, Richard S.; Sevilla, Sara [European Journal of Medicinal Chemistry, 2014, vol. 71, p. 168 - 184]

39
[ 1570-45-2 ]
[ 67-64-1 ]
[ 75055-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isonicotinic acid ethylester With sodium hydride In hexane; N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: acetone In hexane; N,N-dimethyl-formamide; mineral oil at 20℃; for 18h;	5.4.1. 1-[3-(Trifluoromethyl)phenyl]butane-1,3-dione (30) General procedure: Sodium hydride (60% dispersion in oil, 390 mg, 9.75 mmol) was first washed with hexanes to remove the oil and was then suspended in 7 ml dimethylformamide. A solution of methyl 3-(trifluoromethyl)benzoate 29 (1.0 g, 4.9 mmol) in 2 ml dimethylformamide was added drop-wise and with stirring. Upon addition, the mixture was stirred for 1 h at room temperature. Acetone (400 ml, 5.44 mmol) was added drop-wise and the mixture was stirred overnight at room temperature. The mixture was poured into water and the aqueous layer was extracted four times with ether. The aqueous layer was acidified with 2 N hydrochloric acid and was extracted three times with ether. The combined organics were dried over sodium sulphate and evaporated under reduced pressure. The residue was purified using the SP1 Purification System (ethyl acetate-hexane gradient, 0:100 rising to 10:90) to give 30 (640 mg, 2.78 mmol, 56%) as an oil. Purity 100%.

40
[ 1508657-03-1 ]
[ 75055-73-1 ]

Yield	Reaction Conditions	Operation in experiment
58 mg	With hydrogenchloride In water at 80℃; for 1h;

Reference： [1]Korsager, Signe; Nielsen, Dennis U.; Taaning, Rolf H.; Lindhardt, Anders T.; Skrydstrup, Troels [Chemistry - A European Journal, 2013, vol. 19, # 52, p. 17687 - 17691]

41
[ 75055-73-1 ]
methyl-3(5) γ-pyridyl-5(3) pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrazine hydrate In ethanol at 85℃; for 48h;	34.1 34.1 4-(5-Methyl-2H-pyrazol-3-yI)-pyrid me 1-(4-Pyridinyl)-1 ,3-butanedione (815.0 mg; 4.995 mrnol) was suspended in ethanol (6.0 mL), hydrazinium hydroxide (242.8 p1; 4.995 mmol) was added and the mixture was stirred at 85 °C for 48 h. The reaction mixture was diluted with and saturated NaHCO3-solution (pH 7-8) and extracted with dichioromethane. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo; yield: 703 mg (88%) beige solid.
	With hydrazine hydrate In methanol for 2h; Reflux;	17.3 (3) Preparation of 3-methyl-5-p-pyridyl-1-hydropyrazole Add a 100 ml round bottom flask to the magnet and add 1-p-pyridylbutane-1,3-dione inward. (3.26 g, 20 mmol, 1.0 eq) and hydrazine hydrate (1.1 g, 20 mmol, 1.0 eq), Further, 50 ml of methanol was added, and the mixture was heated to reflux for 2 hr and extracted with ethyl acetate. The solvent was evaporated to dryness, and silica gel column chromatography afforded 3-methyl-5-p-pyridyl-1-hydropyrazole

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2015/90496, 2015, A1 Location in patent: Page/Page column 71; 72
[2]Current Patent Assignee: LANZHOU UNIVERSITY - CN108203408, 2018, A Location in patent: Paragraph 0029

42
[ 872-85-5 ]
[ 67-64-1 ]
[ 75055-73-1 ]

Yield	Reaction Conditions	Operation in experiment
42%	With tert.-butylhydroperoxide; di-tert-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid at 120℃; for 24h;	Typical procedure for radical coupling of aldehydes with ketones General procedure: Under air atmosphere, aldehydes (0.3 mmol), TBAI (0.2 equiv),TBHP (2.0 equiv), DTBP (2.0 equiv), p-TsOH (0.1 equiv), and acetoneor other ketones (2 mL) were added to a screw-capped vial.The reaction vial was placed in a temperature-controlled aluminum-heating block set at 120 C. The reaction progress wasmonitored by TLC. After the completion of the reaction, the vialwas removed from the heating block and was left to cool to ambienttemperature. The solution was filtered through a short columnof silica gel and washed with EtOAc. The filtrate was concentratedunder reduced pressure to leave a crude product, which was purifiedby flash column chromatography on silica gel with petroleumether/EtOAc as an eluent to give the desired product

Reference： [1]Shen, Xuqian; Borah, Arun Jyoti; Cao, Xihan; Pan, Weixiang; Yan, Guobing; Wu, Xiangmei [Tetrahedron Letters, 2015, vol. 56, # 46, p. 6484 - 6487]

43
[ 75055-73-1 ]
[ 282724-29-2 ]
(2E,6E)-2,6-bis(3-((Z)-4-oxo-4-(pyridin-4-yl)but-2-en-2-ylamino)benzylidene)cyclohexanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.6%	With formic acid In methanol at 20℃;	Synthesis of compound 3: general procedure General procedure: 2a (0.30 g, 0.001 mol) or 2b (0.32 g, 0.001 mol) and diacetone materials (0.002 mol) were dissolved in methanol (5 mL). Two drops of formic acid were added and the mixture was stirred for 3-8 h at ambient temperature (monitored by TLC). The precipitate was collected and recrystallised from methanol to afford 3a-e. (2E,6E)-2,6-Bis(3-((Z)-4-oxo-4- (pyridin-4-yl)but-2-en-2-ylamino)benzylidene)cyclohexanone (3d): Yellow powder; yield 75.6%; m.p. 82-84 °C; IR (KBr, cm-1): v 1665, 1564, 1433, 1327, 1289, 1215, 1162, 1061, 1009, 765, 732, 683. 1H NMR: δ 13.22 (s, 2H), 8.75 (d, J = 4 Hz, 4H), 7.75-7.35 (s, 6H), 7.30-7.10 (m, 8H), 5.91 (d, J = 8 Hz, 2H), 2.95 (t, J = 4 Hz, 4H), 2.20 (s, 6H), 1.80-1.70 (m, 2H). 13C NMR: δ189.4, 185.8, 163.4, 149.9, 146.1, 137.8, 136.7, 136.4, 135.6, 129.0, 127.9, 125.9, 124.6, 120.3, 94.0, 28.0, 22.3, 20.0. HRMS for C38H35N4O3 [M + H+] calcd 595.2709; found: 595.2703.

Reference： [1]Chen, Qin; Hou, Yun; Hou, Guige; Li, Ning; Cong, Wei; Zhao, Feng; Li, Hongjuan; Wang, Chunhua; Sun, Jufeng [Journal of Chemical Research, 2016, vol. 40, # 7, p. 400 - 403]

44
[ 75055-73-1 ]
[ 762-04-9 ]
diethyl (2-oxo-2-(pyridin-4-yl)ethyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With dipotassium peroxodisulfate; silver(I) acetate In 1,2-dimethoxyethane; water at 85℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;

Reference： [1]Li, Lili; Huang, Wenbin; Chen, Lijin; Dong, Jiaxing; Ma, Xuebing; Peng, Yungui [Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10539 - 10544][Angew. Chem., 2017, vol. 129, # 35, p. 10675 - 10680,6]

45
iron(III) chloride [ No CAS ]
[ 75055-73-1 ]
C₂₇H₂₄FeN₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium methylate In methanol; water for 24h;

Reference： [1]Sanz; O'Connor; Martí-Centelles; Comar; Pitak; Coles; Lorusso; Palacios; Evangelisti; Baldansuren; Chilton; Weihe; McInnes; Lusby; Piligkos; Brechin [Chemical Science, 2017, vol. 8, # 8, p. 5526 - 5535]

46
aluminum(III) nitrate nonahydrate [ No CAS ]
[ 75055-73-1 ]
[ 1195938-76-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium methylate In methanol; water for 1h;

47
iron(III) chloride [ No CAS ]
[ 75055-73-1 ]
C₂₇H₂₄FeN₃O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium methylate In methanol; water

Reference： [1]Sanz, Sergio; O'Connor, Helen M.; Comar, Priyanka; Baldansuren, Amgalanbaatar; Pitak, Mateusz B.; Coles, Simon J.; Weihe, Høgni; Chilton, Nicholas F.; McInnes, Eric J. L.; Lusby, Paul J.; Piligkos, Stergios; Brechin, Euan K. [Inorganic Chemistry, 2018, vol. 57, # 7, p. 3500 - 3506]

48
[ 1122-54-9 ]
[ 141-78-6 ]
[ 75055-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride at 20℃; Cooling with ice;	17.1 2) Preparation of 1-p-pyridylbutane-1,3-dione Add a 100 ml round bottom flask to the magnetizer and add sodium hydride inward. (0.88 g, 22 mmol, purity 60%, 1.1 eq), then 50 ml of ethyl acetate was added under ice bath. Slowly add p-pyridinone (2.42 g, 20 mmol, 1.0 eq), after 30 min in ice bath, React at room temperature for more than 10h, monitor with TLC plate, use after reaction Quenched with 10% ammonium chloride, extracted with ethyl acetate. Obtaining 1-p-pyridylbutane-1,3-dione
	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;	General Procedure for the synthesis of intermediates 2 General procedure: In a 100 ml round bottom flask, substituted acetophenone (30 mmol,1 equiv) and NaH (33 mmol, 1.1 equiv) was dissolved in THF at 0 C. Thecorresponding acid ethyl ester was added and the mixture was stirred at0 C for 30 min. Then, the reaction was stirred at room temperature for12 h. After the reaction was quenched with saturated NH4Cl (50 ml) andextracted with EtOAc (2 × 100 ml), the combined organic layers werewashed with brine (50 ml), dried over Na2SO4, concentrated undervacuum and purified by column chromatography on silica gel to affordthe corresponding product 2.

Reference： [1]Current Patent Assignee: LANZHOU UNIVERSITY - CN108203408, 2018, A Location in patent: Paragraph 0029
[2]Yao, Haiyan; Guo, Quanping; Wang, Mengran; Wang, Rui; Xu, Zhaoqing [Bioorganic and Medicinal Chemistry, 2021, vol. 46]

49
[ 75055-73-1 ]
phenyl 5-methyl-3-(pyridin-4-yl)-1H-pyrazole-1-sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 2 h / Reflux 2: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 70 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / 2 h / Reflux; Inert atmosphere 2: potassium <i>tert</i>-butylate / dimethyl sulfoxide / 10 h / 70 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: LANZHOU UNIVERSITY - CN108203408, 2018, A
[2]Yao, Haiyan; Guo, Quanping; Wang, Mengran; Wang, Rui; Xu, Zhaoqing [Bioorganic and Medicinal Chemistry, 2021, vol. 46]

50
[ 75055-73-1 ]
[ 20007-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In methanol for 2h; Reflux; Inert atmosphere;	General Procedure for the synthesis of intermediates 3 General procedure: In a 100 ml round bottom flask equipped with a condenser tube,corresponding intermediate substrate 2 (10 mmol, 1 equiv) andN2H4H2O (10 mmol, 1 equiv) was dissolved in CH3OH. The reactionwas reflux for 2 h. After the reaction was completed, the organic solventwas removed under vacuum, the residue was purified by column chromatographyon silica gel to afford the corresponding product 3.

Reference： [1]Yao, Haiyan; Guo, Quanping; Wang, Mengran; Wang, Rui; Xu, Zhaoqing [Bioorganic and Medicinal Chemistry, 2021, vol. 46]

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P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
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P230	Keep wetted
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P232	Protect from moisture.
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P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P263	Avoid contact during pregnancy/while nursing.
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P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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
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P401
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

[ CAS No. 75055-73-1 ]

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[ 75055-73-1 ] Synthesis Path-Downstream 1~50

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