[ CAS No. 1129-30-2 ] {[proInfo.proName]}

Name: 1129-30-2|2,6-Diacetylpyridine|97%
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Quality Control of [ 1129-30-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1129-30-2 ]

CAS No. :	1129-30-2	MDL No. :	MFCD00006304
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BEZVGIHGZPLGBL-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	70790
Synonyms :

Calculated chemistry of [ 1129-30-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.63
TPSA :	47.03 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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.74
Log Po/w (XLOGP3) :	0.89
Log Po/w (WLOGP) :	1.49
Log Po/w (MLOGP) :	-0.19
Log Po/w (SILICOS-IT) :	1.99
Consensus Log Po/w :	1.18

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.65
Solubility :	3.65 mg/ml ; 0.0224 mol/l
Class :	Very soluble
Log S (Ali) :	-1.46
Solubility :	5.63 mg/ml ; 0.0345 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.335 mg/ml ; 0.00206 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 1129-30-2 ]

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

Application In Synthesis of [ 1129-30-2 ]

* 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 [ 1129-30-2 ]
Downstream synthetic route of [ 1129-30-2 ]

[ 1129-30-2 ] Synthesis Path-Upstream 1~10

1
[ 1129-30-2 ]
[ 935-28-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With hydrazine In diethylene glycol at 170℃; for 0.5 h; Stage #2: With potassium hydroxide In diethylene glycol at 20 - 200℃; for 2 h;	2, 6-Diacetylpyridine (2g) was dissolved in diethyleneglycol(50mut) with hydrazine monohydrate (3.6ml). The reaction mixture was heated at170 C for 30 min. The reaction mixture was then cooled to room temperature for the addition of potassium hydroxide (3.1g), then heated at200 C for 2h when the reaction mixtue lost all colour. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted with ether, organics combined, washed with brine, dried(MgS04) and concentrated to give desired product (1.5g, 93percent), AH(CDCI3) 1.29 (6H, t, J7. 6Hz), 2.76- 2.82 (4H, q, J 7.6Hz), 6.96 (2H, d, J 7.6Hz), 7.50 (1 H, t, J 7.6Hz).
58%	With sodium hydroxide; hydrazine In diethylene glycol at 120℃; for 16 h;	A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 ml) and 2,6-diacetylpyridine (6g, 36.8 mmol) suspended in diethylene glycol (27 ml_) was cautiously heated to 120 °C for 16 hours. The mixture was cooled to room temperature and partitioned between H₂O and ether. The ether extracts were washed with 1 N NaOH, dried over MgSO₄ and concentrated to a clear oil. Flash column chromatography (0percent to 15percent EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58percent). ¹H NMR (400 MHz, CDCI₃): 5 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H). 2,6-Diethyl-pyridine has also been prepared as follows:A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 ml_ of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCI₂(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether(500 mL).at 0 °C unde₍r N₃ atmosphere. After addition, the resulting mixture was stirred,. , ' >.,"?, '['A V ' "' > 'ambient temperature oveifngh'tj was then heated to reflux for about 3 hours. The suspensiatonwas poured into cushed ice (200 g) and the mixture was saturated with NH₄CI. The organic layer was separated and the aqueous phase was extracted with ether (200 mL x 3). The combined organic layers were washed with water, brine, dried over Na₂SO₄ and concentrated to give the product (41 .1 g, 89percent).

Reference： [1] Patent: WO2005/49023, 2005, A1, . Location in patent: Page/Page column 58
[2] Egyptian Journal of Chemistry, 2000, vol. 43, # 4, p. 297 - 308
[3] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 119
[4] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 36,43
[5] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 307 - 310
[6] Egyptian Journal of Chemistry, 2000, vol. 43, # 4, p. 297 - 308

2
[ 935-28-4 ]
[ 1129-30-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With tert.-butylnitrite; N-hydroxyphthalimide In acetonitrile at 90℃; for 36 h; Schlenk technique	To the 25 mL Schlenk reaction tube was added NHPI 1.0 equivalent, vacuum dried for 15 minutes, oxygen balloon was added, followed by addition of acetonitrile in an oxygen atmosphere, 2.0 equivalents of t-butyl nitrite, 0.5 mmol of 2,6-diethylpyridine, In the reaction tube with poly tetrafluoro plug after the oil into the pot, 90 ° C reaction 36h. After completion of the reaction, the solvent acetonitrile was concentrated under reduced pressure and the column was separated by column chromatography. The eluent was petroleum ether / ethyl acetate (ν: ν = 5: 1) to give 2,6-diacetylpyridine. Product yield 54percent, yellow solid
30%	at 110℃; for 50 h;	Into a 250 ml three-necked flask, 5.4 g of 2,6-diethyl pyridine (40 mmol) and 60 ml of nitrobenzene (1.205 g/ml) are added and refluxed at 110° C. for about 50 h. After the removal of nitrobenzene at a pressure lower than 10 mmHg, a black viscous liquid substance is obtained. The mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:2 is used as an eluent to make silica gel column chromatography on the black viscous liquid substance, and a white product with a weight of 2.0 g and a yield of 30percent is obtained. The product is identified as 2,6-diacetyl pyridine by Mass Spectrometry. (0163) Mass Spectrometry MS-EI: 163. (0164) Nuclear Magnetic Resonance analysis, ¹H NMR (400 MHz, CDCl₃): δ8.22 (d, 2H); 8.00 (t, 1H); 2.80 (s, 1H).

Reference： [1] Patent: CN107011133, 2017, A, . Location in patent: Paragraph 0120; 0121; 0124; 0125
[2] Organic Letters, 2017, vol. 19, # 20, p. 5593 - 5596
[3] Patent: US9266982, 2016, B2, . Location in patent: Page/Page column 34

3
[ 36763-33-4 ]
[ 676-58-4 ]
[ 1129-30-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: at 0 - 20℃; for 3 h; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃;	A solution of MeMgCl in THF (~20percent) (9 mL, 19 mmol) was added dropwise at 0° C to a solution of 2,6-bis(1-pyrrolidinylcarbonyl)pyridine (2.0 g, 7.3 mmol) in anhydrous THF (15 mL). After 3 hours of stirring at room temperature, 30 mL of 2M aq. HCl was added at 0° C and stirred until the evaluation of the gas ceased. The mixture was extracted with СH2Cl2 (3×20 mL). Combined organic phase was dried over Na2SO4. After removal of the solvent in vacuo the product was recrystallized from hexane to yield colorless powder 1.05 g (88percent).

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 3, p. 217 - 219

4
[ 15658-60-3 ]
[ 1129-30-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: With sodium ethanolate In ethyl acetate for 20 h; Reflux Stage #2: With hydrogenchloride In ethyl acetate at 0℃; for 20 h; Reflux	1.1 Preparation of 2, 6-diacetylpyridine[0099] A 3 L 3-neck round bottomed flask was charged with 54.6 g (0.802 mol) of sodium ethoxide. While stirring vigorously with a mechanical stirrer, a solution of 35.5 g (0.159 mol) of 2,6-diethyl pyridinedicarboxylic ester in 300 mL of ethyl acetate was added dropwise to the flask. The resulting slurry was refluxed for 20 h, followed by cooling to 0 ⁰C, and addition of 350 mL (4.2 mol) of concentrated HCl. The mixture was then refluxed for 20 h, forming a white precipitate and a clear yellow solution. Upon cooling, the mixture was added to a separatory funnel containing ~1 L of water. The organic layer was separated; and the aqueous layer was extracted with CH₂Cl₂. The organic layers were combined, washed with saturated Na₂CO₃, dried over Na₂SO₄, and concentrated using rotary evaporation. The resulting brown solid was dissolved in a minimal amount of CH₂Cl₂ (30-50 mL), followed by the addition of an excess (~1 L) of pentane. A dark red- brown side-product was precipitated, and the solution was decanted. This solution was cooled to -78 ⁰C and scraped to produce a tan solid. This was collected on a buchner funnel, and the filtrate repeatedly concentrated and crystallized to yield 16.7 g (65percent, 0.102 mol) of the desired product.

Reference： [1] Patent: WO2011/6044, 2011, A2, . Location in patent: Page/Page column 19

5
[ 3739-94-4 ]
[ 917-54-4 ]
[ 1129-30-2 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 6, p. 797 - 800
[2] Catalysis Letters, 2010, vol. 140, # 3-4, p. 160 - 166

6
[ 15658-60-3 ]
[ 141-78-6 ]
[ 1129-30-2 ]

Reference： [1] Organometallics, 2015, vol. 34, # 7, p. 1170 - 1176
[2] Synthetic Communications, 2005, vol. 35, # 17, p. 2317 - 2324
[3] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 36,43

7
[ 143329-89-9 ]
[ 1129-30-2 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 3031 - 3035

8
[ 5704-66-5 ]
[ 1129-30-2 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 6, p. 1028 - 1030

9
[ 3739-94-4 ]
[ 1129-30-2 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 3, p. 217 - 219

10
[ 1129-30-2 ]
[ 87-62-7 ]
[ 204203-16-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	Reflux	1.2 Preparation of 2,6-Diacetylpyridinebis(2,6-dimethylphenylimine) (hereafter²'^{6 Me2}PDI)[00101 ] A 250 mL round bottom flask was charged with 4.0 g of 2,6-diacetylpyridine,6.09 g (2.05 eq.) of 2,6-dimethylaniline, and 100 mL of methanol. A catalytic amount of /?-toluenesulfonic acid was added; and the reaction mixture was refluxed overnight into a Dean-Stark trap containing potassium sulfate. The reaction mixture was then cooled; and the methanol was reduced to approximately half of its starting volume. The mixture was cooled to -35 ⁰C and the solid was filtered yielding 4.5 g (50percent) of the desired product. The filtrate can be concentrated and cooled to yield more ligand. ¹H NMR (benzene-^, 20⁰C): δ = 8.50 (d, 2H, m-Py), 7.28 (t, IH, p-Py)), 7.08 (d, 4H, m-Ar), 6.99 (t, 2H, p-Ar), 2.17 (s, 6H, CH₃), 2.05 (s, 12H, Ar-CH₃).

Reference： [1] Dalton Transactions, 2017, vol. 46, # 23, p. 7408 - 7411
[2] Chemistry - A European Journal, 2014, vol. 20, # 16, p. 4754 - 4761
[3] Dalton Transactions, 2013, vol. 42, # 24, p. 8802 - 8807
[4] Journal of Molecular Catalysis A: Chemical, 2011, vol. 340, # 1-2, p. 83 - 88
[5] Patent: WO2011/6044, 2011, A2, . Location in patent: Page/Page column 19-20
[6] Polyhedron, 2010, vol. 29, # 14, p. 2862 - 2866
[7] RSC Advances, 2013, vol. 3, # 48, p. 25908 - 25916
[8] Macromolecules, 2014, vol. 47, # 20, p. 7036 - 7042

[ 1129-30-2 ] Synthesis Path-Downstream 1~88

1
[ 1129-30-2 ]
[ 935-28-4 ]

Yield	Reaction Conditions	Operation in experiment
93%		2, 6-Diacetylpyridine (2g) was dissolved in diethyleneglycol(50mut) with hydrazine monohydrate (3.6ml). The reaction mixture was heated at170 C for 30 min. The reaction mixture was then cooled to room temperature for the addition of potassium hydroxide (3.1g), then heated at200 C for 2h when the reaction mixtue lost all colour. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted with ether, organics combined, washed with brine, dried(MgS04) and concentrated to give desired product (1.5g, 93%), AH(CDCI3) 1.29 (6H, t, J7. 6Hz), 2.76- 2.82 (4H, q, J 7.6Hz), 6.96 (2H, d, J 7.6Hz), 7.50 (1 H, t, J 7.6Hz).
58%	With sodium hydroxide; hydrazine; In diethylene glycol; at 120℃; for 16h;Product distribution / selectivity;	A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 ml) and 2,6-diacetylpyridine (6g, 36.8 mmol) suspended in diethylene glycol (27 ml_) was cautiously heated to 120 C for 16 hours. The mixture was cooled to room temperature and partitioned between H2O and ether. The ether extracts were washed with 1 N NaOH, dried over MgSO4 and concentrated to a clear oil. Flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58%). 1H NMR (400 MHz, CDCI3): 5 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H). 2,6-Diethyl-pyridine has also been prepared as follows:A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 ml_ of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCI2(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether(500 mL).at 0 C unde(r N3 atmosphere. After addition, the resulting mixture was stirred,. , ' >.,«?, '['A V ' «' > 'ambient temperature oveifngh'tj was then heated to reflux for about 3 hours. The suspensiatonwas poured into cushed ice (200 g) and the mixture was saturated with NH4CI. The organic layer was separated and the aqueous phase was extracted with ether (200 mL x 3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give the product (41 .1 g, 89%).

Reference： [1]Patent: WO2005/49023,2005,A1 .Location in patent: Page/Page column 58
[2]Egyptian Journal of Chemistry,2000,vol. 43,p. 297 - 308
[3]Patent: WO2006/18725,2006,A1 .Location in patent: Page/Page column 119
[4]Collection of Czechoslovak Chemical Communications,1959,vol. 24,p. 36,43
[5]Archiv der Pharmazie,1980,vol. 313,p. 307 - 310
[6]Egyptian Journal of Chemistry,2000,vol. 43,p. 297 - 308

2
[ 1129-30-2 ]
[ 14150-94-8 ]
[ 131941-29-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2820 - 2827
[2]Journal of the Chemical Society, Dalton Transactions,1997,p. 3765 - 3771

3
[ 1129-30-2 ]
[ 123-46-6 ]
[ 120545-33-7 ]

Reference： [1]Analytical Chemistry,1989,vol. 61,p. 1272 - 1275

4
[ 1129-30-2 ]
[ 1126-58-5 ]
[ 120545-32-6 ]

Reference： [1]Analytical Chemistry,1989,vol. 61,p. 1272 - 1275

5
[ 1129-30-2 ]
[ 52411-34-4 ]
C₂₃H₂₁N₃O₂ [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

6
[ 1129-30-2 ]
[ 158753-17-4 ]
2,6-di(1,10-phenanthrolin-2-yl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 3017 - 3022

7
[ 1129-30-2 ]
[ 24544-04-5 ]
[ 374073-25-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With formic acid In isopropyl alcohol at 70℃; for 12h;
86%	With formic acid In methanol for 24h; Heating;
80%	With acetic acid In ethanol Heating;

80%	With acetic acid In ethanol Heating;
50%	With acetic acid In ethanol at 80℃; for 16h;	1.1.1 1) Synthesis of (1E,1'E)-1,1'-(pyridine-2,6-diyl)bis(N-(2,6-diisopropylphenyl)ethan-1-imine) 2,6-diacetylpyridine (12.6mmol) was dissolved in 34 ml of absolute ethanol, 2,6-diisopropylaniline (2eq) was added, and then a small amount of acetic acid was added, followed by refluxing at 80° C. for 16 hours.When the reaction was completed, the precipitated product was filtered with cold ethanol to obtain a clean yellow solid (yield 50%).
	With acetic acid In ethanol
	With formic acid In methanol Heating;

Reference： [1]Milione, Stefano; Cavallo, Gabriella; Tedesco, Consiglia; Grassi, Alfonso [Journal of the Chemical Society, Dalton Transactions, 2002, # 8, p. 1839 - 1846]
[2]Fan, Rui-Qing; Zhu, Dong-Sheng; Mu, Ying; Li, Guang-Hua; Yang, Yu-Lin; Su, Qing; Feng, Shou-Hua [European Journal of Inorganic Chemistry, 2004, # 24, p. 4891 - 4897]
[3]Britovsek, George J. P.; Bruce, Michael; Gibson, Vernon C.; Kimberley, Brian S.; Maddox, Peter J.; Mastroianni, Sergio; McTavish, Stuart J.; Redshaw, Carl; Solan, Gregory A.; Strömberg, Staffan; White, Andrew J. P.; Williams, David J. [Journal of the American Chemical Society, 1999, vol. 121, # 38, p. 8728 - 8740]
[4]Hiya, Kohji; Nakayama, Yuushou; Yasuda, Hajime [Macromolecules, 2003, vol. 36, # 21, p. 7916 - 7922]
[5]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/12693, 2021, A Location in patent: Paragraph 0137-0142
[6]Britovsek, George J.P.; Gibson, Vernon C.; Kimberley, Brian S.; Maddox, Peter J.; McTavish, Stuart J.; Solan, Gregory A.; White, Andrew J.P.; Williams, David J. [Chemical Communications, 1998, # 7, p. 849 - 850]
[7]Li, Xuefu; Zhu, Dongsheng; Gao, Wei; Zhang, Yuetao; Mu, Ying [Journal of Chemical Research, 2006, # 6, p. 371 - 373]

8
[ 1129-30-2 ]
[ 356-24-1 ]
2,6-Bis(1,3-dioxo-4,4,5,5,6,6,6-heptafluorohexyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3%	With lithium hydride In diethyl ether at 40 - 45℃; for 22h;

Reference： [1]Chizhov; Ratner; Kodess; Pashkevich [Russian Journal of Organic Chemistry, 1998, vol. 34, # 3, p. 340 - 343]

9
[ 1129-30-2 ]
[ 28059-64-5 ]
[ 442858-40-4 ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 648,p. 55 - 61

10
[ 1129-30-2 ]
[ 24544-04-5 ]
1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With methyl hydroperoxide In methanol at 20℃; for 12h;
91%	With formic acid In methanol at 0℃; for 24h; Schlenk technique; Inert atmosphere;	1 2.2. Synthesis of 2-acetyl-6-(arylimino)pyridine compounds ("mono-imino compounds") General procedure: At 0 °C, formic acid (50 ll) was added dropwise to a solution of 2,6-diacetylpyridine (1.63 g; 10 mmol) and the appropriate aniline derivative (9 mmol) in methanol (15 ml). The mixture was kept at 0 C for 24 h without stirring. The desired mono-imino compounds precipitated as bright yellow crystals which were separated by filtration,washed with cold methanol (0 °C), and finally dried in vacuo. Second crops of crystals could be obtained after prolonged storage of the mother liquor at -20 °C. 2.2.1 2-Acetyl-6-[1-(2,6-diisopropylphenyl)iminoethyl]pyridine (2) 1H NMR (400 MHz, CDCl3): δ [ppm] = 8.35 (d, 1H, Py-H), 7.93 (d, 1H, Py-H), 7.73 (t, 1H, Py-H), 6.97 (d, 2H, Ar-H), 6.90 (t, 1H, Ar-H), 2.58 (s, 3H, O=C-CH3), 2.52 (sept, 2H, iPr-CH), 2.06 (s, 3H, N=C-CH3), 0.95 (s, 6H, iPr-CH3), 0.94 (s, 6H, iPr-CH3). 13C{1H} NMR (100 MHz, CDCl3): δ [ppm] = 200.1 (1C, Cq, O=C-CH3), 166.4 (1C, Cq, (ArN)=C-CH3), 155.5 (1C, Cq, Py), 152.5 (1C, Cq, Py), 146.2 (1C, Cq, Ar-C-N), 137.3 (1C, Py-CH), 135.7 (2C, Ar-Cq), 124.5 (1C, Ar-CH), 123.7 (1C, Py-CH), 123.0 (2C, Ar-CH), 122.6 (1C, Py-CH), 28.3 (2C, iPr-CH3), 25.6 (1C, O=C-CH3), 23.2 (1C, iPr-CH3), 22.9 (1C, iPr-CH3), 17.0 (1C, (ArN)=C-CH3). MS [m/z] (rel. intensity in brackets): 322 M+ (38), 307 M-Me (100). Yield: 91%.
87.1%	With formic acid In methanol at 20℃; for 48h;

65%	With formic acid In methanol for 12h;	Synthesis of L₁ Synthesis routes of ligand and complex are depicted in scheme S1. Catalytic amount of formic acid (150 µL) was added by syringe at room temperature to a stirred solution of 2,6-diacetylpyridine (1.630 g, 10.0 mmol) and 2,6-diisopropylaniline (1.70 mL, 1.596 g, 9.0 mmol) in MeOH (15 mL). After 12 h, a yellow solid was formed, and this was filtered off and washed with cold (0 °C) MeOH. The precipitate was characterized as a mixture of the expected product (97%). The solid was suspended in refluxing ethanol and the resulting mixture was filtered while still hot. The solvent was removed from the filtrate under reduced pressure to give pure 1 as pale yellow crystals in 65% yield. M.p. 183 °C. Ft-IR (KBr, cm-1): ν(C=N) 1647 cm-1, ν(C=O) 1699 cm-1. H NMR (300 MHz, CDCl3): 1.16 [d, 6H, CH(CH3)2], 1.17 [d, 6H, CH(CH3)2], 2.30 [s, 3H, C(NAr)CH3], 2.76 [m, 2H, CH(CH3)2], 2.82 [S, 3H, C(O)CH3], 7.11-7.22 [m, 3H, CHAr],7.98 [t, 1H, CH Ar], 8.16 [dd, 1H, CH Ar], 8.59 [dd, 1H, CH Ar] ppm.). Mass (EI, m/z): 322 [M+, 100%].
62%	With formic acid In methanol at 20℃; for 1h;	2 2.48 mg (14 mmoles) of 2,6-di-iso-propylaniline were introduced into a reaction flask together with 5 ml of anhydrous methanol, obtaining a limpid solution. 20 ml of anhydrous methanol containing 1.96 g (12 mmoles) of 2,6-diacetylpyridine and 0.25 ml of formic acid were subsequently added dropwise, at room temperature, to said solution. After about 1 hour, the precipitation of a yellow microcrystalline solid product was observed: said yellow solid product was recovered by filtration, washed with cold methanol and dried, under vacuum, at room temperature, obtaining 2.4 g of a light yellow solid product (yield=62%) having formula (L2a).
62%	With formic acid In methanol at 20℃;	2 Synthesis of ligands of formula (L2) 2.70 ml (0.014 mole) of 2,6-diisopropylaniline was introduced into the reaction flask together with 5 ml of methanol and 0.25 ml of formic acid.Get a solution.Subsequently, 20 ml containing 1.93 g (0.012 mol) was added dropwise to the solution at room temperature.2,6-diacetylpyridine in methanol,A yellow microcrystalline solid precipitated:The yellow solid is recovered by filtration,Wash with cold methanol and dry under vacuum at room temperature,2.4 g of a slightly white solid of the formula (L2) was obtained (yield=62%).
	With formic acid In methanol
	With methyl hydroperoxide In methanol at 20℃; for 16h;
	In methanol

Reference： [1]Haas, Ruth M.; Hern, Zachary; Sproules, Stephen; Hess, Corinna R. [Inorganic Chemistry, 2017, vol. 56, # 24, p. 14738 - 14742]
[2]Görl, Christian; Betthausen, Eva; Alt, Helmut G. [Polyhedron, 2016, vol. 118, p. 37 - 51]
[3]Liu, Changkun; Jin, Guoxin [New Journal of Chemistry, 2002, vol. 26, # 10, p. 1485 - 1489]
[4]Rahimipour, Enayat; Zohuri, Gholamhossein; Kimiaghalam, Mahsa; Khoshsefat, Mostafa [Inorganica Chimica Acta, 2020, vol. 502]
[5]Current Patent Assignee: ENI SPA - US9475897, 2016, B2 Location in patent: Page/Page column 21
[6]Current Patent Assignee: ENI SPA - TWI577686, 2017, B Location in patent: Page/Page column 33; 34
[7]Location in patent: scheme or table Badiei, Yosra M.; Jiang, Yunbo; Widger, Leland R.; Siegler, Maxime A.; Goldberg, David P. [Inorganica Chimica Acta, 2012, vol. 382, # 1, p. 19 - 26]
[8]Hess, Corinna R.; Hofmann, Andreas J.; Jandl, Christian [European Journal of Inorganic Chemistry, 2020, vol. 2020, # 5, p. 499 - 505]
[9]Gao, Jiahao; Lin, Wenhua; Liu, Hua; Ma, Yanping; Sun, Wen-Hua; Zhang, Liping; Zhang, Qiuyue [Molecules, 2020, vol. 25, # 18]

11
[ 1129-30-2 ]
[ 34124-14-6 ]
1-[6-(1-{(E)-2-[2-(2-Amino-phenyl)-ethyl]-phenylimino}-ethyl)-pyridin-2-yl]-ethanone [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 221 - 226

12
[ 1129-30-2 ]
[ 20605-01-0 ]
2,6-bis(5,5-diethyloxycarbonyl-2-methyl-1,3-dioxan-2-yl)pyridine [ No CAS ]

Reference： [1]Heterocyclic Communications,2004,vol. 10,p. 139 - 144

13
[ 1129-30-2 ]
[ 80058-84-0 ]
2,6-diacetylpyridinebis(4-bromo-2,6-diisopropylanil) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2005,vol. 690,p. 1233 - 1239

14
[ 1129-30-2 ]
[ 4102-53-8 ]
C₂₅H₂₅I₂N₃ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 4580 - 4592

15
[ 1129-30-2 ]
[ 63285-53-0 ]

Reference： [1]Chemische Berichte,1992,vol. 125,p. 701 - 710

16
[ 1129-30-2 ]
[ 87-63-8 ]
2,6-diacetylpyridinebis(2-chloro-6-methylphenylimine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.2%	With formic acid; In methanol; at 20℃;Heating / reflux;	Experiment 12,6-Diacetylpyridinebis(2-chloro-6-methylphenylimine) In a 200 mL round bottom flask, 2.0 g of 2,6-diacetylpyridine (FW 163.18, 0.0122 mole) and 50 mL of methanol were placed. Next, 3.45 g of <strong>[87-63-8]2-chloro-6-methylaniline</strong> (FW 141.60, 0.0245 mole) was added followed by three drops of formic acid and the solution was stirred at RT under nitrogen for four d, at which time no precipitate had formed. The reaction was then refluxed for 24 h. GC analysis indicated that reaction was incomplete. Refluxing was continued for a total of 1 week. Solvent was stripped from the reaction mixture via rotovap. Flash chromatography through a basic alumina column (eluted with hexane/ethyl acetate 20:1) lead to isolation of an oil. The oil was then crystallized from methanol/methylene chloride. Collected 0.21 g (4.2% yield) of pale yellow crystals. 1H-NMR (ppm, CDCl3): 2.12(s, 6H), 2.32(s, 6H), 6.95(t, 2H), 7.13(d, 2H), 7.30(d, 2H), 7.92(t, 1H), 8.5(d, 2H).

Reference： [1]Patent: EP1066229,2004,B1 .Location in patent: Page 9

17
[ 1129-30-2 ]
[ 88-05-1 ]
(E)-1-(6-(1-((2,4,6-trimethylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In ethanol at 20℃; for 24h;	1 25.2 g (155 mmol) of 2,6-diacetylpyridine were dissolved in ethanol in an open beaker at ambient temperature. 21.7 ml (155 mmol) of 2,4,6-trimethylaniline was then added to the beaker, followed by the addition of several drops of acetic acid. After one day, yellow crystals of the compound of structure 2 began to form, and were collected and washed with cold ethanol. Additional crops were collected without crystallization over several days and combined, for a total yield of 40.06 g (93%). The product was identified as the compound having structure E1, which is an embodiment of structure 2, by 1H NMR. 1H NMR (CDCl3) δ8.58 (d, 1H, Hpy), δ8.12 (d, 1H, Hpy) δ7.90 (t, 1H, Hpy) δ6.90 (s, 2H, Hmes), δ2.80 (s, 3H, acylne CH3), δ2.30 (s, 3H, imine CH3), δ2.23 (s, 3H, p-CH3), δ2.00 (s, 6H, o-CH3).
	With formic acid In methanol at 0℃; Inert atmosphere; Schlenk technique;
	With acetic acid In methanol; water Cooling with ice;

Reference： [1]Current Patent Assignee: PHILLIPS 66; CHEVRON CORP - US2006/128958, 2006, A1 Location in patent: Page/Page column 27
[2]Zhang, Qiuyue; Li, Zilong; Han, Mingyang; Xiang, Junfeng; Solan, Gregory A.; Ma, Yanping; Liang, Tongling; Sun, Wen-Hua [Catalysis science and technology, 2021, vol. 11, # 2, p. 656 - 670]
[3]Liu, Tian; Ma, Yanping; Solan, Gregory; Liang, Tongling; Sun, Wen-Hua [Applied Organometallic Chemistry, 2021, vol. 35, # 7]

18
[ 1129-30-2 ]
[ 4073-98-7 ]
C₃₅H₃₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In ethanol; at 20℃; for 96h;	10.0 g (61 mmol) of 2,6-diacetylpyridine and 6.24 g (25 mmol) of <strong>[4073-98-7]4,4'-methylenebis(2,6-dimethylaniline)</strong> were dissolved in ethanol in an open beaker at ambient temperature. The beaker was covered with a watch glass overnight, after which time a very small amount of suspended cloudy precipitate had begun to form. The beaker was then left uncovered for four days, after which time a light yellow crystalline solid was collected and washed with ethanol. Successive crops were collected in the same manner, combined, and identified as the compound having structure E2, an embodiment of structure 18, by 1H NMR. The total yield was 12.18 g (91percent). 1H NMR (CDCl3) delta8.58 (d, 2H, Hpy) delta8.14 (d, 2H, Hpy) delta7.94 (t, 2H, Hpy) delta6.96 (s, 4H, Haryl), delta3.88 (s, 2H, CH2), delta2.80 (s, 6H, ketone CH3), delta2.26 (s, 6H, imine CH3), delta2.03 (s, 12H, aryl CH3).

Reference： [1]Patent: US2006/128958,2006,A1 .Location in patent: Page/Page column 27

19
[ 1129-30-2 ]
[ 2246-44-8 ]
2,6-bis(1-(2-methyl-1-naphthylimino)-ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; acetic acid;	b) Synthesis of 2,6-bis(1-(2-methyl-1-naphthylimino) ethyl]pyridine 1.20 g (7.35 mmol) of 2,6-diacetylpyridine dissolved in 25 ml of ethanol were introduced into a 100 ml round-bottomed flask under nitrogen, with stirring. 3.0 g (20.25 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> dissolved in 10 ml of ethanol were then added dropwise, followed by 0.1 ml of glacial acetic acid. The mixture was heated at reflux for 18 hours, with stirring, then cooled to ambient temperature and dried in vacuo so as to obtain crude 2,6-bis[1-(2-methyl-1-naphthylimino)-ethyl]pyridine, which was dissolved in methylene chloride and neutralized with an aqueous solution of sodium carbonate.
	With sodium carbonate; In ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate;	b) Synthesis of 2,6-bis[1-(2-methyl-1-naphthylimino) ethyl]pyridine. 1.20 g (7.35 mmol) of 2,6-diacetylpyridine dissolved in 25 ml of ethanol were introduced into a 100 ml round-bottomed flask under nitrogen, with stirring. 3.0 g (20.25 mmol) of <strong>[2246-44-8]1-amino-2-methylnaphthalene</strong> dissolved in 10 ml of ethanol were then added dropwise, followed by 0.1 ml of glacial acetic acid. The mixture was heated at reflux for 18 hours, with stirring, then cooled to ambient temperature and dried in vacuo so as to obtain crude 2,6-bis[1-(2-methyl-1-naphthylimino)-ethyl]pyridine,which was dissolved in methylene chloride and neutralized with an aqueous solution of sodium carbonate. The organic phase was separated, and 100 ml of water were added thereto. After dewatering and evaporation of the organic phase, the 2,6-bis[1-(2-methyl-1-naphthylimino)ethyl]pyridine was purified by liquid chromatography on a silica column using a 25/75 v/v AcOEt/n-hexane mixture as eluent. This gave 1.33 g of yellow microcrystalline solid. 1H NMR (CDCl3- 300K - 500 MHz) delta = 2.26 (m, 12H, -CH 3imine and -CH 3 naphthyl), 7.45 (m, 6H, H5-6-7 naphth), 7.58 (d, 2H, H8 naphth, 3JH7-H8~ 8 Hz), 7.65 (d, 2H, H3 naphth,3JH3-H4~ 8 Hz), 7.85 (d, 2H, H4 naphth) 8.06 (t, 1H, Hp py,3JHm-Hp~ 8 Hz), 8.68 (d, 2H, Hm py, 3JHm-Hp~ 8 Hz) in ppm. FTIR (KBr pressing) nu = 1640 (nuC=N) imine) in cm-1.

Reference： [1]Patent: US2003/18147,2003,A1
[2]Patent: EP1260515,2002,A1

20
[ 1129-30-2 ]
[ 765-39-9 ]
2,6-bis[1-(1-pyrrolylimino)ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
350 mg (57%)	silica gel; In toluene;	11. Preparation of 2,6-bis[1-(1-pyrrolylimino)ethyl]pyridine (11) 2,6-Diacetylpyridine (345 mg, 2.11 mmol) and <strong>[765-39-9]1-aminopyrrole</strong> (400 mg, 4.87 mmol) were dissolved in 50 ml of toluene. To this solution, molecular sieves (4 A) were added. After standing for 2 days at room temperature, the mixture was filtered. The solvent was removed in vacuo. The residue was crystallized from ethanol. Yield 350 mg (57%) of diimine 11. 1H-NMR (CDCl3) delta8.26 (d, 2H, Py-Hm), 7.82 (t, 1H, Py-Hp), 6.93 (m, 2H, PyrH), 6.25 (m, 2H, PyrH), 2.66 (s, 6H, Me).

Reference： [1]Patent: US2003/119921,2003,A1

21
[ 1129-30-2 ]
[ 95-53-4 ]
[ 210537-32-9 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; In dichloromethane;	EXAMPLE 1 Preparation of 2,6-bis-[1-(2-methylphenylimino)ethyl]pyridine, (VII) One g of 2,6-diacetylpyridine and 3.0 ml of o-toluidine were added to an Erlenmeyer flask with 20 ml of methylene chloride. A stirbar and 5 drops of 97% formic acid were added, and the flask was sealed and the solution was stirred for 40 hours. The solvent was then removed in vacuo, and the flask was placed in the freezer at -30 C. The resulting viscous oil was washed with cold methanol, and a yellow solid formed and was isolated by filtration and identified by 1 H NMR as the desired product (959 mg, 45.9%). 1 H NMR (CDCl3): δ 8.38(d, 2, Hpyr), 7.86(t, 1, Hpyr), 7.20(m, 4, Haryl), 7.00(t, 2, Haryl), 6.67(d, 2, Haryl), 2.32(s, 6, N=C--CH3), 2.10(s, 6, CH3 aryl).

Reference： [1]Journal of Molecular Catalysis A: Chemical,2011,vol. 340,p. 83 - 88
[2]Patent: US6103946,2000,A
[3]Polyhedron,2010,vol. 29,p. 2862 - 2866
[4]Inorganica Chimica Acta,2011,vol. 373,p. 47 - 53

22
[ 1129-30-2 ]
[ 6926-58-5 ]
[ 344422-39-5 ]

Yield	Reaction Conditions	Operation in experiment
45.9%	In ethanol at 65℃; for 3h;
2.72 g (73%)	In ethanol; acetic acid	a 2,6-Diacetylpyridine bis-(4,4-dimethylthiosemicarbazone) 2,6-Diacetylpyridine bis-(4,4-dimethylthiosemicarbazone) A mixture of 4,4-dimethylthiosemicarbazide (2.70 g, 0.022 mol) and 2,6-diacetylpyridine (1.63 g, 0.10 mol) in 95% EtOH (45 ml) containing glacial acetic acid (0.5 ml) was heated by a steam bath for 1 h and 10 min and allowed to cool to ambient temperature. The yellow precipitate was collected by filtration, washed with 95% EtOH, and subsequently recrystallized from toluene: yield 2.72 g (73%); mp 215° (dec).
	With acetic acid In ethanol Reflux;

In ethanol at 60℃; for 12h;

4.1; 4.2 (1) Taking the 2, 6 - diacetyl pyridine (0.815 g, 5 mmol) is dissolved in 20 ml of ethanol, for 60 °C stirring 15 min, make the solution;(2) In solution made by adding 4, 4 - dimethyl thiosemicarbazide (1.19 g, 10 mmol) in 60 °C reflux stirring reaction 12 h, cooled to the room temperature after the reaction is poured into the beaker in after volatilization, after filtering the resulting light yellow precipitate, anhydrous ethanol washing 3 times, be ligand L4

Reference： [1]Li, Shanhe; Khan, Muhammad Hamid; Wang, Xiaojun; Cai, Meiling; Zhang, Juzheng; Jiang, Ming; Zhang, Zhenlei; Wen, Xiao-An; Liang, Hong; Yang, Feng [Dalton Transactions, 2020, vol. 49, # 47, p. 17207 - 17220]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4719221, 1988, A
[3]Akladios, Fady N.; Andrew, Scott D.; Parkinson, Christopher J. [Journal of Biological Inorganic Chemistry, 2016, vol. 21, # 8, p. 931 - 944]
[4]Current Patent Assignee: GUANGXI NORMAL UNIVERSITY - CN109651414, 2019, A Location in patent: Paragraph 0048-0051

23
[ 1129-30-2 ]
[ 5266-85-3 ]
2,6-bis{1-[(2-methyl-6-isopropylphenyl)imino]ethyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.02 g (78%)	In ethanol;	Preparation of the ligand, 2,6-bis{1-[(2-methyl-6-isopropylphenyl)imino]ethyl}pyridine <strong>[5266-85-3]2-methyl-6-isopropylaniline</strong> (1.45 mL, 9.2 mmol) was added to a solution of 2,6-diacetylpyridine (500 mg, 3 mmol) in absolute ethanol (12 mL). After the addition of several drops of glacial acetic acid, the solution was refluxed for 48 hours. Upon cooling at room temperature, the product crystallized from ethanol. The pale yellow solid formed was washed with cold ethanol (2 x 6 mL) and it was dried in vacuo at 60 ØC for two days. Yield: 1.02 g (78 %). 1H NMR (CDCl3, 300 MHz): delta 8.46 (d, 2H, JH-H = 7.9 Hz, py-Hm), 7.90 (t, 1H, JH-H = 7.9 Hz, py-Hp), 7.17-6.98 (m, 6H, Ph), 2.81 (spt, 2H, JH-H = 6.8 Hz, CH(CH3)2), 2.24 (s, 6H, N=CMe), 2.02 (s, 6H, Me), 1.18 (d, 6H, JH-H = 6.8 Hz, CH(CH3)2), 1.12 (d, 6H, JH-H = 6.8 Hz, CH(CH3)2). 13C{1H} NMR (CDCl3, 75.4 MHz, plus APT): delta 167.3 (N=C), 155.3 (py, Co), 147.7 (Ar, Cip), 136.9 (py, Cp), 136.4 (Ar, Co), 127.8 (Ar, Cp), 125.1 (Ar, Co), 123.4 (Ar, Cm), 123.2 (Ar, Cm), 122.3 (py, Cm), 28.2 (CH(CH3)2), 23.0 (CH(CH3)2), 22.7 (CH(CH3)2), 18.0 (N=C-Me), 16.7 (Me).

Reference： [1]Patent: EP1325924,2003,A1

24
[ 1129-30-2 ]
[ 88-05-1 ]
1-(6-[1-(2,4,6-trimethylphenylimino)ethyl]pyridin-2-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With formic acid In methanol at 20℃;	3 Synthesis of Ligand Having Formula (L3) 0.80 ml (0.0057 mole) of 2,4,6-trimethylaniline was introduced into the reaction flask together with 5 ml of methanol and 2 drops of formic acid.Get a solution.Then add dropwise to the solution at room temperature5 ml contains 0.937 g (0.0057 mole)2,6-diacetylpyridine in methanolgives a yellow microcrystalline solid:The yellow solid is recovered by filtration,Wash with cold methanol and dry under vacuum at room temperature,1.2 g of a pale yellow solid of formula (L3) was obtained (yield = 75%).
26%	With toluene-4-sulfonic acid In propan-1-ol at 20℃; for 36h;	2 Example 2; 1 -I6-M -(2,4,6-Trimethyl-phenylimino)-ethyll-pyridin-2-yl)-ethanone (13); 1-(6-Acetyl-pyridin-2-yl)-ethanone (20.0 g, 0.123 mol), 14.92 g(0.110) of 2,4,6-trimethylphenylamine and 300 ml of n-propanol with a few crystals of p-toluenesulfonic acid were stirred at room temperature for 36 hours in 500 ml flask under the flow of the nitrogen. The resultant yellow precipitate was filtered and washed with 20 ml of methanol. It was then dried under vacuum overnight. The yield of 13 was 9.01 g (26%) as a yellow solid.1H NMR (500 MHz, CD2CI2, TMS): δ 1.90 (s, 6 H, Me), 2.20 (s, 3 H, Me), 2.28 (s, 3 H1 Me), 2.75 (s, 3 H, Me), 6.90 (s, 2H, Arom-H), 7.90 (t, 3JHH=8.0 HZ, 1 H, Py-H), 8.09 (d, 3JHH=8.0 HZ, 1 H, Py-H), 8.55 (d, 3JHH=8.0 Hz, 1 H, Py-H). 13C NMR (500 MHz, CD2CI2, TMS (selected signals)): δ 167.3 (C=N), 200.0 (C=O). Anal. Calculated for C18H20N2O (MoI. Wt: 280.36): C, 77.11 ; H, 7.19; N, 9.99. Found: C, 77.13; H, 7.20; N, 10.20.
	In methanol

Reference： [1]Current Patent Assignee: ENI SPA - TWI577686, 2017, B Location in patent: Page/Page column 34; 35
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2007/21955, 2007, A2 Location in patent: Page/Page column 16
[3]Gao, Jiahao; Lin, Wenhua; Liu, Hua; Ma, Yanping; Sun, Wen-Hua; Zhang, Liping; Zhang, Qiuyue [Molecules, 2020, vol. 25, # 18]

25
[ 1129-30-2 ]
[ 579-66-8 ]
(E)-1-{6-[1-(2,6-diethylphenylimino)-ethyl]pyridin-2-yl}ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 2; Preparation of 1- { 6- [1- (2 , 6-diethylphenylimino) - ethyl] pyridin-2-yl } ethanone; 10.35 g of 2, 6-diacetylpyridine (0.0634 mol), 7.10 g of 2, 6-diethylaniline (0.0476 mol) and 2 ml of formic acid were stirred in 300 ml of heptane at room temperature for 71 h. The insoluble solid was filtered off <n="52"/>(11.10 g) and dissolved in 150 ml of toluene and the solution was extracted with 10 ml of a saturated Na2CO3 solution. The toluene phase was dried over Na2SO4 and filtered and the solvent was distilled off in vacuo. 5.58 g (0.0198 mol) of the product were obtained in a purity of 99% (GC/MS) in a yield of 40%. The mother liquor of the reaction solution was freed completely from the solvent and the residue was recrystallized from hot heptane. 2.00 g (0.0068 mol) of the product were additionally obtained in a purity of 100% (GC/MS) . The total yield was 54%.

Reference： [1]Patent: WO2007/80081,2007,A2 .Location in patent: Page/Page column 50-51

26
[ 1129-30-2 ]
[ 39478-78-9 ]
2,6-bis-[1-(5-bromo-2-methylphenylimino)-ethyl]-pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	toluene-4-sulfonic acid; In toluene; for 72h;Heating / reflux;	1-(6-Acetyl-pyridin-2-yl)ethanone [8.33 g (0.051 mol)], 20.0 g (0.107 mol) of 5-bromo-2-methyl-pheny.amine and 200 ml of dry toluene with a few crystals of para-toluenesulfonic acid were refluxed under the flow of the nitrogen using a Dean-Stark trap for 3 d until the calculated <n="20"/>amount of the water was separated (1.84 mi). The solvent was removed in a rotary evaporator and the resultant reaction mixture was recrystallized from 50 ml of ethanol. The yield of 26 was 19.88 g (78%) as a pale yellow solid. 1H NMR (500 MHz, C6D6, TMS): delta 1.90 (s, 6 H, Me), 2.12 (s, 6 H, Me), 6.50 (m, 2H, Arom-H), 7.20 (m, 4H, Arom-H), 7.30 (t, 3JHH=7.8 HZ, 1 H1 Py-H), 8.40 (d, 3JHH=7.8 HZ, 2H, Py-H). 13C NMR (500 MHz, C6D6, (selected signals)): delta 167.4 (C=N). Anal. Calculated for C23H2IBr2N3 (MoI. Wi: 499.24): C, 55.33; H, 4.24; N, 8.42. Found: C, 55.48; H, 4.45; N, 8.53.

Reference： [1]Patent: WO2007/59015,2007,A1 .Location in patent: Page/Page column 18-19

27
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 373-02-4 ]
[ 5193-03-3 ]
Ni(C₁₉H₁₇Cl₂N₇)OH(H₂O)⁽¹⁺⁾*PF₆^(1-)=[Ni(C₁₉H₁₇Cl₂N₇)OH(H₂O)]PF₆ [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

28
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 557-34-6 ]
[ 5193-03-3 ]
Zn(C₁₉H₁₇Cl₂N₇)⁽²⁺⁾*2PF₆^(1-)=[Zn(C₁₉H₁₇Cl₂N₇)](PF₆)2 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

29
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 71-48-7 ]
[ 5193-03-3 ]
Co(C₁₉H₁₇Cl₂N₇)(H₂O)2⁽²⁺⁾*2PF₆^(1-)=[Co(C₁₉H₁₇Cl₂N₇)(H₂O)2](PF₆)2 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

30
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 5193-03-3 ]
[ 7646-85-7 ]
Zn(C₁₉H₁₇Cl₂N₇)⁽²⁺⁾*2PF₆^(1-)=[Zn(C₁₉H₁₇Cl₂N₇)](PF₆)2 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

31
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 5193-03-3 ]
[ 7646-79-9 ]
Co(C₁₉H₁₇Cl₂N₇)(H₂O)2⁽²⁺⁾*2PF₆^(1-)=[Co(C₁₉H₁₇Cl₂N₇)(H₂O)2](PF₆)2 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

32
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 5193-03-3 ]
copper dichloride [ No CAS ]
Cu(C₁₉H₁₇Cl₂N₇)Cl(H₂O)⁽¹⁺⁾*PF₆^(1-)=[Cu(C₁₉H₁₇Cl₂N₇)Cl(H₂O)]PF₆ [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

33
ammonium hexafluorophosphate [ No CAS ]
[ 1129-30-2 ]
[ 5193-03-3 ]
nickel dichloride [ No CAS ]
Ni(C₁₉H₁₇Cl₂N₇)OH(H₂O)⁽¹⁺⁾*PF₆^(1-)=[Ni(C₁₉H₁₇Cl₂N₇)OH(H₂O)]PF₆ [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1987,vol. 126,p. 187 - 194

34
iron(III) chloride hexahydrate [ No CAS ]
[ 1129-30-2 ]
[ 515-96-8 ]
[ 338974-57-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With NH₃ In methanol; water refluxed for about 30 min; filtered; elem. anal.;

Reference： [1]Bacchi, Alessia; Ivanovic-Burmazovic, Ivana; Pelizzi, Giancarlo; Andjelkovic, Katarina [Inorganica Chimica Acta, 2001, vol. 313, # 1-2, p. 109 - 119]

35
[ 1129-30-2 ]
neodymium(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
Nd⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*2H₂O*3C₂H₅OH = [Nd(C₂₃H₂₁N₃O₂)](ClO₄)3*2H₂O*3C₂H₅OH [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

36
[ 1129-30-2 ]
lanthanum(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
La⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*2C₂H₅OH = [La(C₂₃H₂₁N₃O₂)](ClO₄)3*2C₂H₅OH [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

37
[ 1129-30-2 ]
erbium(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
Er⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*4H₂O = [Er(C₂₃H₂₁N₃O₂)](ClO₄)3*4H₂O [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

38
[ 1129-30-2 ]
gadolinium(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
Gd⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*5H₂O = [Gd(C₂₃H₂₁N₃O₂)](ClO₄)3*5H₂O [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

39
[ 1129-30-2 ]
hydrated cerium perchlorate [ No CAS ]
[ 52411-34-4 ]
Ce⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*C₂H₅OH = [Ce(C₂₃H₂₁N₃O₂)](ClO₄)3*C₂H₅OH [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

40
[ 1129-30-2 ]
praseodymium(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
Pr⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*5.5C₂H₅OH = [Pr(C₂₃H₂₁N₃O₂)](ClO₄)3*5.5C₂H₅OH [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

41
[ 1129-30-2 ]
holmium(III) perchlorate hydrate [ No CAS ]
[ 52411-34-4 ]
Ho⁽³⁺⁾*C₂₃H₂₁N₃O₂*3ClO₄^(1-)*7H₂O = [Ho(C₂₃H₂₁N₃O₂)](ClO₄)3*7H₂O [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1996,p. 1493 - 1498

42
[ 1129-30-2 ]
copper(II) acetate dihydrate [ No CAS ]
[ 515-96-8 ]
Cu(H₂O)(C₅H₃N(C(CH₃)NN(C(O))2NH₂)2)*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	In ethanol; water refluxing; filtering, crystn. (room temp., 24 h), filtering, washing (H2O); elem. anal.;

Reference： [1]Andjelkovic; Ivanovic; Niketic; Prelesnik; Leovac [Polyhedron, 1997, vol. 16, # 24, p. 4221 - 4228]

43
[ 1129-30-2 ]
manganese(II) perchlorate tetrahydrate [ No CAS ]
[ 515-96-8 ]
[Mn(2,6-diacetylpyridinebis(semioxamazide))(methanol)(H₂O)](ClO₄)2*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol 2,6-diacetylpyridine and semioxamazide added to MeOH, mixt. stirred at 55°C for 1 h, Mn salt added; MeCN added, stored for 4 d, crystals sepd.; elem. anal.;

Reference： [1]Liu, Gao-Feng; Filipovic, Milos; Heinemann, Frank W.; Ivanovic-Burmazovic, Ivana [Inorganic Chemistry, 2007, vol. 46, # 21, p. 8825 - 8835]

44
[ 1129-30-2 ]
iron(III) nitrate tetrahydrate [ No CAS ]
[ 515-96-8 ]
[Fe(2,6-diacetylpyridinebis(semioxamazide))(H₂O)2](NO₃)2*H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In methanol; acetonitrile 2,6-diacetylpyridine and semioxamazide mixed in MeOH/MeCN, mixt. refluxed for 2 h under Ar, Fe salt added, mixt. refluxed for 1 h; H2O added, cooled to room temp., stored for 5 h, crystals filtered off, washed with acetone, dried in air; elem. anal.;

Reference： [1]Liu, Gao-Feng; Filipovic, Milos; Heinemann, Frank W.; Ivanovic-Burmazovic, Ivana [Inorganic Chemistry, 2007, vol. 46, # 21, p. 8825 - 8835]

45
[ 1129-30-2 ]
[ 6945-92-2 ]
cobalt(II) perchlorate hexahydrate [ No CAS ]
CoCl₂(C₅H₃N(C(CH₃)NNHCH₂COOCH₃)2) [ No CAS ]

Reference： [1]Journal of Thermal Analysis and Calorimetry,2001,vol. 66,p. 759 - 778

46
[ 1129-30-2 ]
[ 1950-68-1 ]
[ 1192878-53-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 1128 - 1136

47
[ 1129-30-2 ]
[ 16947-63-0 ]
C₂₅H₂₅N₅O₄ [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2009,vol. 694,p. 3793 - 3799

48
[ 1129-30-2 ]
[ 13194-73-5 ]
2,6-bis(1-(3,5-dibromo-4-methylphenylimino)ethyl)pyridine [ No CAS ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2010,vol. 322,p. 45 - 49

49
[ 1129-30-2 ]
[ 452-77-7 ]
[ 339267-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	SiO2/Al2O3 pellets; In toluene; at 45℃; for 24h;Molecular sieve;	10 g mole sieves (4A) and 0.5 g of catalytically active SiO2/Al2O3 pellets were added to a solution of 0.49 g (3.0 mmol) diacetylpyridine in toluene. After addition of 7.0 mmol of the respective aniline, the solution was heated at 45 C. for 24 hours. After filtration over Na2SO4 and evaporation to dryness, the products were precipitated as yellow solids from methanol overnight at -20 C. (73-94%).Spectroscopic data: 1a: 1H NMR (400 MHz, CDCl3): 8.30 (d, 2H, Py-Hm), 7.85 (t, 1H, Py-Hp), 7.15 (t, 2H, Ph-H), 6.53 (m, 4H, Ph-H), 2.39 (s, 6H, NCMe), 2.26 (s, 6H, Ph-CH3). 13C {1H} (100.5 MHz, CDCl3): 167.9 (Cq), 163.1 (Cq), 159.9 (Cq), 155.3 (Cq), 150.4 (Cq), 136.9 (CH), 131.6 (CH), 122.4 (CH), 114.8 (CH), 106.6 (CH), 16.2 (CH3), 14.1 (CH3). MS data: 377 (M?+) (88), 362 (12), 150 (100).

Reference： [1]Journal of Molecular Catalysis A: Chemical,2010,vol. 322,p. 45 - 49
[2]Patent: US2011/71294,2011,A1 .Location in patent: Page/Page column 5

50
[ 1129-30-2 ]
[ 123-46-6 ]
2,6-diacetylpyridine bis(Girard-T hydrazone)dichloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol;	The white ligand H2LCl2·4H2O was synthesized via the reaction of 2,6-diacetylpyridine and Girard?s Treagent as described previously [31] and used in the synthesis of complexes without further purification.IR: 3394 (s), 3115 (m), 3071 (m), 3020 (m), 2969 (w), 2934 (w), 1709 (vs), 1630 (w), 1568 (w), 1489(m), 1423 (m), 1366 (w), 1329 (w), 1281 (m), 1228 (m), 1153 (w), 1123 (w), 993 (w), 949 (w), 922 (w), 855(w), 827 (w), 744 (w), 702 (w), 663 (w).

Reference： [1]Inorganic Chemistry Communications,2010,vol. 13,p. 1085 - 1088
[2]Journal of Coordination Chemistry,2016,vol. 69,p. 2754 - 2765

51
[ 1129-30-2 ]
[ 87-62-7 ]
[ 204203-16-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	toluene-4-sulfonic acid; In methanol;Reflux;	1.2 Preparation of 2,6-Diacetylpyridinebis(2,6-dimethylphenylimine) (hereafter2'6 Me2PDI)[00101 ] A 250 mL round bottom flask was charged with 4.0 g of 2,6-diacetylpyridine,6.09 g (2.05 eq.) of 2,6-dimethylaniline, and 100 mL of methanol. A catalytic amount of /?-toluenesulfonic acid was added; and the reaction mixture was refluxed overnight into a Dean-Stark trap containing potassium sulfate. The reaction mixture was then cooled; and the methanol was reduced to approximately half of its starting volume. The mixture was cooled to -35 0C and the solid was filtered yielding 4.5 g (50percent) of the desired product. The filtrate can be concentrated and cooled to yield more ligand. 1H NMR (benzene-^, 200C): delta = 8.50 (d, 2H, m-Py), 7.28 (t, IH, p-Py)), 7.08 (d, 4H, m-Ar), 6.99 (t, 2H, p-Ar), 2.17 (s, 6H, CH3), 2.05 (s, 12H, Ar-CH3).

Reference： [1]Dalton Transactions,2017,vol. 46,p. 7408 - 7411
[2]Chemistry - A European Journal,2014,vol. 20,p. 4754 - 4761
[3]Dalton Transactions,2013,vol. 42,p. 8802 - 8807
[4]Journal of Molecular Catalysis A: Chemical,2011,vol. 340,p. 83 - 88
[5]Patent: WO2011/6044,2011,A2 .Location in patent: Page/Page column 19-20
[6]Polyhedron,2010,vol. 29,p. 2862 - 2866
[7]RSC Advances,2013,vol. 3,p. 25908 - 25916
[8]Macromolecules,2014,vol. 47,p. 7036 - 7042

52
[ 1129-30-2 ]
[ 24544-04-5 ]
[ 204203-14-5 ]
1-(6-(1-((2,6-diisopropylphenyl)imino)ethyl)pyridin-2-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	toluene-4-sulfonic acid; In methanol;Reflux;	8.1 Preparation of l-{6-[(2,6-Diisopropylphenyl)ethanimidoyl]-2-pyridinyl}-l- ethanone.A 250 mL round bottom flask was charged with 5.00 g (30.64 mmol) of 2,6- diacetylpyridine, 6.00 g (33.84 mmol) of 2,6-diisopropylaniline, and 100 mL of methanol. A catalytic amount ofp-toluenesulfonic acid was added and the reaction mixture was re fluxed overnight. The reaction mixture was then cooled to approximately 35 0C to 40 0C and filtered to remove 2,6-bis[l-(2,6- diisopropylphenylimino)ethyl]pyridine. The reaction solution was then placed at 0 0C for 24 hours, and the solid was filtered, yielding 4.25 g (43 %) of the desired product as a yellow powder. 1H NMR (benzene-^, 20 0C): δ = 1.21-1.14 (2 d, 12H, CH2CH5), 2.19 (s, 3Η, CH3), 2.52 (s, 3H, CH3), 2.88(sep, 2H, CH2CH3), 7.05-7.13 (m, 3H, Ar) and CH2CH3), 7.21 (t, IH, p-py), 7.94 (d, IH, py), 8.45 (d, IH, py).

Reference： [1]Patent: WO2011/6044,2011,A2 .Location in patent: Page/Page column 22-23
[2]Dalton Transactions,2018,vol. 47,p. 16876 - 16884

53
[ 1129-30-2 ]
[ 24544-04-5 ]
[ 204203-14-5 ]

Yield	Reaction Conditions	Operation in experiment
75.2%	With formic acid; In methanol; for 12h;Reflux; Inert atmosphere;	General procedure: For synthesis of ligand 2a, a reaction mixture of 2,3- butanedione(2.0 g, 0.023 mol), aniline (4.33 g, 0.047 mol), a few dropsof formic acid and methanol (20 ml) was refluxed for 12 h andcooled to room temperature. A yellow crystal-like solid precipitated after several hours.
75%	With toluene-4-sulfonic acid; In toluene; for 10h;Inert atmosphere; Dean-Stark; Heating;	60 ml of dry toluene was introduced to a 100 ml flask under a nitrogen atmosphere, and further 2,6-diisopropylaniline (1.063 g, 6 mmol), 2,6-diacetylpiridine (0.4575 g, 2.8 mmol) and a catalystic amount of paratoluenesulfonic acid were added. The mixture was stirred with heating for 10 hours using a Dean-Stark water separator. The reaction mixture was cooled to room temperature and the toluene was removed using an evaporator. Ethanol (40 ml) was added to the remained solid content and the insoluble solid was separated by filtration. The remained insoluble solid was washed again with ethanol to thereby obtain the pyridine diimine compound as the precursor of the iron complex (5-1) in a yield of 75%. Note that the purity was confirmed by GC and the peak at MS401 was also confirmed by GC-MS.
	In ethanol; for 40h;Reflux;	The ligand was synthesized by reacting 1 equivalent of 2,6-diacetylpyridine with 2 equivalents of 2,6-diisopropylaniline in ethanol and allowed to reflux for 40 h. Then the ligand solution was complexed with ferrous chloride in butanol to yield a dark blue precipitate. The complex was dried under vacuum and the yielding was 1.5 g of catalyst.

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 4754 - 4761
[2]New Journal of Chemistry,2010,vol. 34,p. 2599 - 2604
[3]Journal of the American Chemical Society,2012,vol. 134,p. 4998 - 5003
[4]Cuihua Xuebao/Chinese Journal of Catalysis,2013,vol. 34,p. 1560 - 1569
[5]Patent: US10815317,2020,B2 .Location in patent: Page/Page column 20
[6]Journal of the American Chemical Society,2012,vol. 134,p. 11900 - 11903
[7]Journal of the American Chemical Society,2019,vol. 141,p. 10099 - 10108
[8]Applied Catalysis A: General,2014,vol. 475,p. 179 - 185
[9]RSC Advances,2013,vol. 3,p. 25908 - 25916

54
[ 1129-30-2 ]
[ 393-39-5 ]
[ 844634-44-2 ]

Reference： [1]Organometallics,2012,vol. 31,p. 1143 - 1149
[2]Journal of Molecular Catalysis A: Chemical,2011,vol. 340,p. 83 - 88

55
[ 1129-30-2 ]
[ 445-02-3 ]
[ 853786-02-4 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2011,vol. 340,p. 83 - 88

56
[ 1129-30-2 ]
[ 445-03-4 ]
[ 853786-03-5 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2011,vol. 340,p. 83 - 88

57
[ 1129-30-2 ]
[ 98276-57-4 ]
C₂₃H₁₇N₅ [ No CAS ]

Reference： [1]Chinese Journal of Chemistry,2010,vol. 28,p. 1547 - 1552

58
[ 1129-30-2 ]
[ 4637-24-5 ]
[ 63285-53-0 ]

Reference： [1]European Journal of Inorganic Chemistry,2011,p. 3431 - 3437

59
[ 1129-30-2 ]
[ 5369-19-7 ]
[ 1326217-94-0 ]

Reference： [1]Journal of Molecular Catalysis A: Chemical,2012,vol. 352,p. 110 - 127
[2]Applied Catalysis A: General,2011,vol. 403,p. 25 - 35

60
[ 1129-30-2 ]
[ 2380-36-1 ]
[ 1326217-95-1 ]

Reference： [1]Journal of Coordination Chemistry,2012,vol. 65,p. 2415 - 2431
[2]Journal of Molecular Catalysis A: Chemical,2012,vol. 352,p. 110 - 127
[3]Applied Catalysis A: General,2011,vol. 403,p. 25 - 35
[4]Journal of Coordination Chemistry,2015,vol. 68,p. 2054 - 2064

61
[ 1129-30-2 ]
[ 626-40-4 ]
[ 1351616-19-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With silica-alumina In toluene at 40 - 45℃; Molecular sieve; Inert atmosphere;

Reference： [1]Location in patent: experimental part Görl, Christian; Beck, Nadine; Kleiber, Katharina; Alt, Helmut G. [Journal of Molecular Catalysis A: Chemical, 2012, vol. 352, p. 110 - 127]

62
[ 1129-30-2 ]
cadmium(II) chloride monohydrate [ No CAS ]
[ 6945-92-2 ]
CdCl₂(C₅H₃N(CCH₃NNHCH₂COOC₂H₅)2)*1.5H₂O [ No CAS ]

Reference： [1]Polyhedron,2012,vol. 31,p. 19 - 28

63
[ 1129-30-2 ]
[ 363-81-5 ]
[ 473442-35-2 ]

Reference： [1]Organometallics,2012,vol. 31,p. 1143 - 1149

64
C₂₈H₃₃ClFeN₃O₂S⁽²⁺⁾*2Cl^(1-) [ No CAS ]
[ 1129-30-2 ]
[ 24544-04-5 ]
[ 2987-49-7 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 2·MeOH (14.0mg, 23mumol) was dissolved in 5.0mL of CH2Cl2 and transferred to a pressure vessel equipped with a side-arm. Excess O2(g) was bubbled into the solution for 5min and the vessel was put under a slight positive pressure of O2 before being sealed and heated to 60C. The reaction was monitored by LDI-MS over the course of several days. After 96h the reaction was complete as evidenced by the absence of peaks for either the sulfide starting material or sulfoxide intermediate observed in the LDI-MS spectrum. The crude reaction mixture was then stirred with 5mL of 1M HCl for 1h before being neutralized with NaHCO3. The organic layer was then collected and dried. The 1H NMR spectrum of the crude mixture allowed for the identification of the S-oxygenated product, 2-(methylsulfonyl)aniline, delta(CDCl3)=3.06. This peak corresponds to the literature value [81].

Reference： [1]Polyhedron,2013,vol. 58,p. 179 - 189

65
[ 1129-30-2 ]
[ 4848-43-5 ]
C₃₇H₃₇N₃P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With toluene-4-sulfonic acid; In toluene; at 80℃; under 760.051 Torr; for 24h;Glovebox; Inert atmosphere; Molecular sieve;	A 250-mL thick-walled glass bomb was charged with 0.407 g (2.49 mmol) of 2,6- diacetylpyridine, 1 .120 g (4.89 mmol) of 2-(diphenylphosphino)-1 -ethylamine, 0.010 g (0.060 mmol) of p-toluenesulfonic acid, 10 mL toluene, and approximately 10 cm3 of 4 A molecular sieves. The initial pale yellow solution was set to stir at 80 C for 24 hours. After cooling to ambient temperature, the bomb was transferred to a glovebox where the resulting solution was filtered through Celite with excess diethylether. The solvent was then removed in vacuo to yield a yellow oil. The oil was dissolved in approximately 2 mL of diethylether and the resulting solution was placed in the glovebox freezer at -35 C. After 24 h, a light yellow crystalline solid had precipitated. Decanting the mother liquor and subsequent drying allowed the isolation of 1 .098 g (72%) of a crystalline yellow solid identified as Ph2PEtPDI.[00164] Analysis for C39H41N3P2: Calcd C, 75.88; H, 6.73; N, 6.85. Found C, 75.85; H, 6.92; N, 6.74. 1 H NMR (CDCI3): <5 7.93 (d, 7.8 Hz, 2H, m-pyr), 7.62 (t, 7.8 Hz, 1 H, p-pyr), 7.49 (t, 6 Hz, 8H, o-phenyl), 7.33 (m, 12 H, m-phenyl, p-phenyl), 3.68 (pseudo quart, 7.4 Hz, 4H, CH2), 2.56 (t, 8 Hz, 4H, CH2), 2.29 (s, 6H, N=CCH3). 1H NMR (benzene-de): δ 8.27 (d, 7.8 Hz, 2H, m-pyr), 7.52 (t, 7.6 Hz, 8H, o-phenyl), 7.25 (t, 7.8 Hz, 1 H, p-pyr), 7.08 (m, 12H, m-phenyl, p-phenyl), 3.65 (pseudo quart, 7.2 Hz, 4H, CH2), 2.58 (t, 7.6 Hz, 4H, CH2), 2.12 (s, 6 H, N=CCH3). 13C NMR (benzene- cfe): <5 165.72 (N=C), 155.87 {o-pyr), 139.49 (d, JCp = 14.2 Hz, phenyl), 135.85 (p- pyr), 132.85 (d, JCp = 19.5 Hz, phenyl), 128.32 (d, JCp = 6.7 Hz, phenyl), 128.23 {phenyl), 121 .19 {m-pyr), 49.48 (d, JCp = 20.2 Hz, CH2), 30.35 (d, JCp = 12.7 Hz, CH2), 22.31 (N=C), 12.93 (CH2CH2). 31 P NMR (CDCI3): (5 -16.50 (PPh2). 31 P NMR (benzene-de): 5 -16.52 (PPh2).

Reference： [1]European Journal of Inorganic Chemistry,2013,p. 4430 - 4442
[2]Patent: WO2014/201082,2014,A1 .Location in patent: Paragraph 00163-00164

66
[ 1129-30-2 ]
[ 304-20-1 ]
bis(phthalazine-1-hydrazone)-2,6-diacetylpyridine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In methanol; water; for 0.5h;Reflux;	1-Hydrazinophtalazine hydrochloride (5mmol, 1.00g) was dissolved in the mixture of 30cm3 methanol and 5cm3 distilled water with mild heating. To this solution 2,6-diacetylpyridine (2.5mmol, 0.41g) dissolved in 10cm3 methanol was added. The reaction mixture was refluxed for 30min. After cooling the amorphous orange precipitate is filtered off, washed with methanol and air dried. Yield: 90%.

Reference： [1]Polyhedron,2014,vol. 80,p. 142 - 150

67
[ 1129-30-2 ]
[ 34124-14-6 ]
C₄₆H₄₂N₆ [ No CAS ]

Reference： [1]Organometallics,2014,vol. 33,p. 5316 - 5323

68
[ 1129-30-2 ]
[ 21198-18-5 ]
[ 1217351-88-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid In methanol for 4h; Reflux;	Synthesis of H2L A methanol solution of 4-cyclohexyl-3-thiosemicarbazide(2.08 g, 12 mmol) was refluxed with 2,6-diacetylpyridine(0.978 g, 6 mmol) in 30 mL methanol continuously for4 h after adding a few drops of acetic acid. The mixturewas allowed to cool to room temperature and kept for12 h. The yellow precipitate was filtered off, washed withmethanol and dried over P4O10 in vacuo. Yield, 82 %.Elemental Anal. Calcd. (%) for C23H35N7S2: C, 58.32; H,7.45; N, 20.70. Found: C, 58.48; H, 7.39; N, 20.57. -IR[KBr, n (cm 1)]: 3335, 3298 and 3157 (N-H), 2930 and 2 8 5 4 ( c y c l o h e x y l ) , 1 6 3 5 ( CDN), 1154 (N-N), 782 (CDS).-UV/Vis (MeOH, λ(nm)): 235, 314. -1H NMR (CDCl3,ppm): 14.20 (s, 2H, NH), 8.72 (s, 2H, NH), 8.65 (s, 2H,py), 7.77 (t, J D 7.8 Hz, 1H, py), 2.44 (s, 6H, Me), 2.42 (s,2H, C6H11), 2.17-2.14 (m, 8H, C6H11), 1.79-1.76 (m, 8H,C6H11), 1.70-1.66 (m, 4H, C6H11).

Reference： [1]Yu, Han; Zhang, Gaofeng; Li, Mingxue; Lu, Yanli; Wu, Hechen [Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2015, vol. 45, # 12, p. 1864 - 1869]

69
[ 1129-30-2 ]
[ 123-46-6 ]
C₁₉H₃₃N₇O₂⁽²⁺⁾*2Cl^(1-)*4H₂O [ No CAS ]

Reference： [1]Journal of Coordination Chemistry,2016,vol. 69,p. 801 - 811

70
[ 935-28-4 ]
[ 1129-30-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With tert.-butylnitrite; N-hydroxyphthalimide; In acetonitrile; at 90℃; for 36h;Schlenk technique;	To the 25 mL Schlenk reaction tube was added NHPI 1.0 equivalent, vacuum dried for 15 minutes, oxygen balloon was added, followed by addition of acetonitrile in an oxygen atmosphere, 2.0 equivalents of t-butyl nitrite, 0.5 mmol of <strong>[935-28-4]2,6-diethylpyridine</strong>, In the reaction tube with poly tetrafluoro plug after the oil into the pot, 90 C reaction 36h. After completion of the reaction, the solvent acetonitrile was concentrated under reduced pressure and the column was separated by column chromatography. The eluent was petroleum ether / ethyl acetate (nu: nu = 5: 1) to give 2,6-diacetylpyridine. Product yield 54%, yellow solid
30%	With nitrobenzene; at 110℃; for 50h;	Into a 250 ml three-necked flask, 5.4 g of <strong>[935-28-4]2,6-diethyl pyridine</strong> (40 mmol) and 60 ml of nitrobenzene (1.205 g/ml) are added and refluxed at 110 C. for about 50 h. After the removal of nitrobenzene at a pressure lower than 10 mmHg, a black viscous liquid substance is obtained. The mixed solution of ethyl acetate and petroleum ether with a volume ratio of 1:2 is used as an eluent to make silica gel column chromatography on the black viscous liquid substance, and a white product with a weight of 2.0 g and a yield of 30% is obtained. The product is identified as 2,6-diacetyl pyridine by Mass Spectrometry. (0163) Mass Spectrometry MS-EI: 163. (0164) Nuclear Magnetic Resonance analysis, 1H NMR (400 MHz, CDCl3): delta8.22 (d, 2H); 8.00 (t, 1H); 2.80 (s, 1H).

Reference： [1]Patent: CN107011133,2017,A .Location in patent: Paragraph 0120; 0121; 0124; 0125
[2]Organic Letters,2017,vol. 19,p. 5593 - 5596
[3]Patent: US9266982,2016,B2 .Location in patent: Page/Page column 34

71
[ 1129-30-2 ]
[ 929-59-9 ]
dysprosium(III) chloride hexahydrate [ No CAS ]
C₁₅H₂₃ClDyN₃O₃⁽²⁺⁾*2Cl^(1-)*5H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In methanol at 50℃; for 18h; Reflux;	2.2.1. Synthesis of Dy(L2)Cl3.6H2O (5) 2,6-Diacetylpyridine (1 eq., 612 mg, 3.76 mmol) was added to a solution of DyCl36H2O (1 eq., 1.41 g, 3.76 mmol) in MeOH (30 mL). The solution was heated to 50 °C and then 2,2'-(ethylenedioxy)bis(ethylamine) (1 eq., 550 μL, 3.76 mmol) was added in one portion. The reaction mixture was heated to 85 °C and refluxed for 18 h. The solvent volume was reduced by half, and the mixture was cooled to r.t. An excess of Et2O was then added, and the resulting precipitate was collected by filtration and washed with cold Et2O to give 5 as an orange solid (2.36 g, 96%); FAB-MS: m/z = 297 [L2+Na]+ (9%); IR (KBr, cm-1): 3375 (br, OAH), 3007 (s, CAH), 1625 (m, CN), 1593 (m, py), 1460 (w, CAH), 1095 (m, CAO), 1017 (m, py); UV-Vis (MeOH, nm): λmax = 250 (ε = 5140), 274 (ε = 4050), 315 (ε = 4410); CHN: Found: C, 27.94; H, 4.92; N, 6.39%; Calc. for (C15H21N3O2Cl3Dy)6H2O: C, 27.62; H, 5.10; N, 6.44.

Reference： [1]Gavey, Emma L.; Pilkington, Melanie [Polyhedron, 2016, vol. 108, p. 122 - 130]

72
[ 1129-30-2 ]
manganese(II) chloride tetrahydrate [ No CAS ]
[ 52411-34-4 ]
C₂₃H₂₁Cl₂MnN₃O₂*2H₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.2%	In ethanol; at 50 - 85℃; for 4h;	Diacetylpyridine (0.134 g, 0.82 mmol) was added in one portion to a solution of MnCl2-4H2O (0.142 g, 0.82 mmol) in EtOH (30 mL). The solution was heated to 50 C., and then 1,4-bis-(2-aminophenyl)-1,4-dioxabutane (0.200 g, 0.82 mmol) was added in one portion. The reaction mixture was heated to 85 C. and refluxed for 4 h. The solvent volume was reduced by half, and the mixture was cooled to r.t. An excess of Et2O was added, and the resulting precipitate was collected by Buchner filtration and washed well with cold Et2O to give 3 as an orange solid (62 mg, 14.2%). IR (cm-1) 3351, 3072, 2968, 2924, 1671, 1592, 1503, 1362, 1249, 1210, 1087. FAB-MS: m/z=461 [M-Cl]+ (10%). Anal. calcd. for (C23H21N3O2C1-2Mn)0-2H2O C, 55.55; H, 4.26; N, 8.45. found C, 55.72; H, 4.65; N, 8.39%

Reference： [1]Patent: US2016/362434,2016,A1 .Location in patent: Paragraph 0522-0523

73
[ 15529-49-4 ]
[ 1129-30-2 ]
[ 79060-88-1 ]
[RuCl(2,6-diacetylpyridine)(PPh₃)₂]BArF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In dichloromethane; at 20℃; for 1h;Schlenk technique; Inert atmosphere;	A Schlenk flask containing [RuCl2(PPh3)3] (0.501 g, 0.52 mmol), 2,6-diacetylpyridine (dap) (0.090 g, 0.55 mmol), and sodium tetrakis[3,5- bis(trifluoromethyl)phenyl]borate (NaBArF, 0.486 g, 0.55 mmol) was purged and filled with N2. Distilled CH2Cl2 was added and the mixture was allowed to stir at room temperature for 1 hour, during which the wine-red solution transitioned to a deep purple color. The CH2Cl2 solution was filtered through a cotton-filled pipette to remove sodium chloride then vacuum dried to a residue. The residue was then dissolved in a minimal amount of distilled methanol (3 mL) and washed three times with hexanes (3 mL). The red alcohol solution was dried to yield a dark purple solid (0.810 g, 0.48 mmol, 92 %). The solid product is readily recrystallized from methylene chloride layered with hexanes to yield dark purple crystals suitable for characterization by X-ray crystallography. 1H NMR (300 MHz, CDCl3) d 7.93 (d, 2H, JHH=3.9 Hz), 7.83 (dd, 1H, JHH=5.3 Hz), 7.69 (s, 8H), 7.49 (s, 4H), 7.38-7.17 (m, 21H), 6.99-6.91 (m, 6H), 6.71-6.55 (m, 5H), 2.77 (s, 6H, 2CH3). 13C{1H} NMR (75 MHz, CDCl3)3 d 212.4 (s, C=O), 135.0 (s), 134.5 (s), 134.3 (s), 133.7 (s), 133.2 (s), 131.2 (s), 130.5 (s), 130.4 (s), 129.3 (s), 128.8 (s), 128.7 (s), 128.6 (s), 128.4 (s), 126.5 (s), 122.9 (s), 117.7 (s), 26.3 (s). 31P{1H} NMR (121 MHz, CDCl3) d 45.3 (d, JPP=33.6 Hz), 32.2 (d, JPP=33.5 Hz). 19F{1H} NMR (282 MHz, CDCl3) d -62.3 (s). IR (neat, solid): = 3059 (w), 2922 (w), 1610 (w), 1572 (w), 1482 (w), 1352 (m), 1275 (s), 1114 (s), 998 (w), 925 (w), 882 (m), 837 (m), 743 (m) cm-1. m.p. 179-181 C decomp. MS (FAB) m/z 1652 [M + BArF - Cl]+, 824 [M]+, 789 [M - Cl]+. C77H51BClF24NO2P2Ru (1687.18): calcd. C 54.81, H 3.05; found C 54.83, H 3.17.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 873 - 877

74
[ 1129-30-2 ]
[ 5331-43-1 ]
C₂₅H₂₅N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol; at 20℃;	0.166g (1mmol) of <strong>[5331-43-1]benzyl carbazate</strong> and 0.082g (0.5mmol) of 2,6-diacetylpyridine were combined in 20mL of methanol. Slow evaporation of the solvent from the mixture at room temperature resulted in a white crystalline precipitate which was isolated and washed with doubly- distilled water. Ligand bc2-dap: Colorless, 80% yield with respect to the amount of base (<strong>[5331-43-1]benzyl carbazate</strong>) taken. Anal. Calc. for C25H25N5O4: C, 65.36; H, 3.96; N, 15.25. Found: C, 65.15; H, 3.40; N, 14.95%. IR (cm-1): 3246, 1694, 1573, 1038. 1H NMR (400MHz, DMSO-d6): delta 10.55 (s, 1H), 10.44 (s, 1H), 7.82-8.22 (m, 3H), 7.33-7.46 (m, 10H), 5.24 (s, 2H), 5.23 (s, 2H), 2.39 (s, 3H), 2.35 (s, 3H).

Reference： [1]Polyhedron,2018,vol. 141,p. 5 - 16

75
[ 1129-30-2 ]
[ 5331-43-1 ]
Mn⁽²⁺⁾*NO₃^(1-)*6H₂O [ No CAS ]
[ 1147550-11-5 ]
C₂₇H₂₅MnN₇O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In propan-1-ol; water; at 20℃; for 48h;	General procedure: <strong>[5331-43-1]Benzyl carbazate</strong> (0.166g, 1mmol) was dissolved in 10mL of a 16 propanol solution of 17 2,6-diacetylpyridine (0.082g, 0.5mmol). To this solution the various metal nitrates (M(NO3)2·6H2O, (Mn=0.144g, Co=0.146g, Zn=0.149g), 0.5mmol; Fe(NO3)3·9H2O, 0.202g, 0.5mmol) were added together with 18 ammonium thiocyanate (0.076g, 1mmol) dissolved in 10mL of doubly-distilled 19 water. The resulting mixture was kept at room temperature for crystallization. After two days, the manganese, 1, iron, 2, and zinc, 4, complexes were obtained as crystalline solids. In the case of 20 cobalt, both red, 3, and orange, 5, crystals were observed in the solution after two days and were isolated by filtration. These crystals were separated manually and used for further analysis.

Reference： [1]Polyhedron,2018,vol. 141,p. 5 - 16

76
[ 1129-30-2 ]
[ 5331-43-1 ]
cobalt(II) nitrate hexahydrate [ No CAS ]
[ 1147550-11-5 ]
[Co(NCS)₂(bc-dap)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With zinc(II) nitrate hexahydrate; In propan-1-ol; water; at 20℃;	To a 10mL 16 propanol solution of <strong>[5331-43-1]benzyl carbazate</strong> (0.083g, 0.5mmol) and 17 2,6-diacetylpyridine (0.082g, 0.5mmol), a 10mL aqueous solution containing 35 cobalt(II) nitrate hexahydrate (0.146g, 0.5mmol), 36 zinc(II) nitrate hexahydrate (0.149g, 0.5mmol) and 18 ammonium thiocyanate (0.076g, 1mmol) was added slowly with constant stirring. The resulting orange solution was kept at room temperature for slow evaporation of the solvent. X-ray quality green crystals of 8 were obtained after two days and separated as before. Compound 8: Dark green, 72% yield with respect to the amount of metal salt taken. Anal. Calc. for C17H14N5O2S2Co: Co, 13.30; C, 46.06; H, 3.16; N, 15.80; S, 14.45. Found: Co, 13.10; C, 45.90; H, 3.05; N, 15.45; S, 14.10%. IR (cm-1): 3068, 2091, 1734, 1694, 1518, 1053. 1H NMR (400MHz, DMSO-d6): delta 10.57 (s, 1H), 7.91-8.22 (m, 3H), 7.33-7.46 (m, 5H), 5.23 (s, 2H), 2.50 (s, 3H), 2.38 (s, 3H).

Reference： [1]Polyhedron,2018,vol. 141,p. 5 - 16

77
Iron(III) nitrate nonahydrate [ No CAS ]
[ 1129-30-2 ]
[ 5331-43-1 ]
[ 1147550-11-5 ]
C₂₇H₂₅FeN₇O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In propan-1-ol; water; at 20℃; for 48h;	General procedure: <strong>[5331-43-1]Benzyl carbazate</strong> (0.166g, 1mmol) was dissolved in 10mL of a 16 propanol solution of 17 2,6-diacetylpyridine (0.082g, 0.5mmol). To this solution the various metal nitrates (M(NO3)2·6H2O, (Mn=0.144g, Co=0.146g, Zn=0.149g), 0.5mmol; Fe(NO3)3·9H2O, 0.202g, 0.5mmol) were added together with 18 ammonium thiocyanate (0.076g, 1mmol) dissolved in 10mL of doubly-distilled 19 water. The resulting mixture was kept at room temperature for crystallization. After two days, the manganese, 1, iron, 2, and zinc, 4, complexes were obtained as crystalline solids. In the case of 20 cobalt, both red, 3, and orange, 5, crystals were observed in the solution after two days and were isolated by filtration. These crystals were separated manually and used for further analysis.

Reference： [1]Polyhedron,2018,vol. 141,p. 5 - 16

78
[ 1129-30-2 ]
[ 643-28-7 ]
2-acetyl-6-[1-((2-isopropylphenyl)imino)ethyl]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With formic acid In methanol at 20℃; for 48h;	4 Synthesis of ligands of formula (L4) 2 g (0.012 moles) of 2,6-diacetylpyridine in methanoland Five drops of formic acid were introduced into the reaction flask together to obtain a solution.Then add dropwise to the solution at room temperature5 ml of methanol containing 0.80 ml (0.057 mole) of 2-isopropylaniline.48 hours laterCool the solution to 4°C,A yellow microcrystalline solid precipitated:The yellow solid is recovered by filtration,Wash with cold methanol and dry under vacuum at room temperature,0.9 g of a pale yellow solid of formula (L4) was obtained (yield=27%).

Reference： [1]Current Patent Assignee: ENI SPA - TWI577686, 2017, B Location in patent: Page/Page column 35; 36

79
[ 1129-30-2 ]
nickel(II) perchlorate hexahydrate [ No CAS ]
[ 105-83-9 ]
Ni(Me₃[14]pydieneN₄) perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 65%		To an ethanol solution (60 mL) of 2,6-Diacetylpyridine(3.26 g, 0.02 mol) was added Nickel(II) perchlate hexahydrate(7.3 g, 0.02 mol). The mixture solution was heated toabout 65 C and 2.9 g 0.02 mol) of 3,3?-diamino-(N-methyl)dipropylamine was added, and the solution was refluxed forabout 6 h, after which the solution was condensed on a rotaryevaporator to reduce the volume of the solution to about 15mL. After filtering the remaining solution to remove the tinyinsoluble materials, excess of ether was added to precipitatethe target compound. The product was collected by filtration,washed with ether and dried in air. Yield: about 65%. Anal.Calcd. for C16H24Cl2N4NiO8: C, 36.26; H, 4.57; N, 10.57%.Found: C, 36.21; H, 4.51; N, 10.68%.

Reference： [1]Journal of Chemical Sciences,2018,vol. 130

80
[ 1129-30-2 ]
[ 7646-78-8 ]
[ 1643-39-6 ]
C₃₇H₄₉Cl₂N₃O₂Sn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In methanol; at 65℃; for 0.5h;	(L' is dianion of deprotonated 2,6-bis[2,4-di-tert-butyl-6-(ethylidenylamino)phenol]pyridine (II). 2,6-Diacetylpyridine (1 mmol, 0.163 g), 2-amino-4,6-di-tert-butylphenol( 2 mmol, 0.442 g), and SnCl4 (1 mmol, 0.261 g) were mixed in a solution of methanol (20 mL) at 65. The reaction mixture was stirred for 30 min to the formation of a dark violet precipitate. The obtained product was collected on the Schott filter and washed methanol (5 mL). The yield was 0.515 g (68%). For C37H49N3O2Cl2Sn Anal. calcd., % C, 58.67 H, 6.52 N, 5.55 Cl, 9.36 Sn, 15.67 Found, % C, 58.68 H, 6.48 N, 5.57 Cl, 9.40 Sn, 15.69 IR (Nujol), nu, cm-1: 1596 s, 1522 s, 1443 s, 1361 s, 1264 s, 1204 s, 1174 s, 842 s, 828 s, 777 s. 1H NMR (CDCl3, 293 K), delta, ppm: 1.32 (s, 18H, t-Bu), 1.57 (s, 18H, t-Bu), 2.92 (s, 6 H, J (119Sn-1H) =130.1 Hz, CH3), 7.27 (d, 2 H, J = 1.8 Hz, Harom), 7.43 (d, 2 H, J = 1.8 Hz, Harom), 7.95-8.00 (m, 2 H, HPy), 8.19 (t, 1 H, J = 7.8 Hz, HPy). 13C NMR (CDCl3), delta, ppm: 18.4 (CH3, J (119Sn-13C) = 17.6 Hz), 29.47, 31.42 (CH3(t-Bu)), 34.38, 35.66 (C(t-Bu)), 116.1 (J (119Sn-13C) = 29.9 Hz), 123.8 (J (119Sn-13C) = 10.2 Hz),125.8 (J (119Sn-13C) = 105.85 Hz), 128.1, 137.5,139.7 (J (119Sn-13C) = 56.9 Hz), 143.2, 145.6 (J (119Sn-13C) = 44.8 Hz), 146.4 (J (119Sn-13C) =27.2 Hz) (arom), 158.6 (C=N, J (119Sn-13C) = 32.4 Hz). 119Sn NMR (CDCl3, 293 K), delta, ppm: -667.11.

Reference： [1]Russian Journal of Coordination Chemistry,2018,vol. 44,p. 138 - 146
Koord. Khim.,2018,vol. 44,p. 49 - 57,9

81
[ 1129-30-2 ]
[ 87-62-7 ]
[ 204203-16-7 ]
[ 395656-36-7 ]

Reference： [1]Dalton Transactions,2018,vol. 47,p. 16876 - 16884
[2]Dalton Transactions,2018,vol. 47,p. 16876 - 16884
[3]Organometallics,2019,vol. 38,p. 4066 - 4070

82
[ 1129-30-2 ]
[ 33228-44-3 ]
2-acetyl-6-{1-[(4-amylphenyl)imino]ethyl}pyridine [ No CAS ]
2,6-bis{1-[(4-amylphenyl)imino]ethyl}pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 48 %Spectr. 2: 33%	With magnesium sulfate; toluene-4-sulfonic acid In neat (no solvent) at 21 - 23℃; for 4h; Sealed tube; Milling;

Reference： [1]Shaw, Thomas E.; Shultz, Lorianne R.; Garayeva, Louiza R.; Blair, Richard G.; Noll, Bruce C.; Jurca, Titel [Dalton Transactions, 2018, vol. 47, # 47, p. 16876 - 16884]

83
[ 1129-30-2 ]
manganese(II) perchlorate hexahydrate [ No CAS ]
[ 136-64-1 ]
C₆₈H₆₀Mn₄N₂₀O₈⁽⁸⁺⁾*8ClO₄^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 7283 - 7288

84
[ 1129-30-2 ]
[ 54010-75-2 ]
[ 136-64-1 ]
C₆₈H₆₀N₂₀O₈Zn₄⁽⁸⁺⁾*8CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 7283 - 7288

85
iron(II) triflate [ No CAS ]
[ 1129-30-2 ]
[ 136-64-1 ]
C₆₈H₆₀Fe₄N₂₀O₈⁽⁸⁺⁾*8CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 7283 - 7288

86
[ 1129-30-2 ]
[ 84902-24-9 ]
2,6-bis(8-methylquinolin-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol at 95℃; for 16h; Inert atmosphere;

Reference： [1]Li, Chenghao; Pan, Yixiao; Feng, Yu; He, Yan-Mei; Liu, Youran; Fan, Qing-Hua [Organic Letters, 2020, vol. 22, # 16, p. 6452 - 6457]

87
[ 1129-30-2 ]
[ 84902-24-9 ]
C₁₇H₁₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In ethanol at 95℃; for 16h; Inert atmosphere;

Reference： [1]Li, Chenghao; Pan, Yixiao; Feng, Yu; He, Yan-Mei; Liu, Youran; Fan, Qing-Hua [Organic Letters, 2020, vol. 22, # 16, p. 6452 - 6457]

88
[ 1129-30-2 ]
cobalt(II) perchlorate hexahydrate [ No CAS ]
[ 136-64-1 ]
C₆₈H₆₀Co₄N₂₀O₈⁽⁸⁺⁾*8ClO₄^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 7283 - 7288

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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. 1129-30-2 ] {[proInfo.proName]}

Quality Control of [ 1129-30-2 ]

Related Doc. of [ 1129-30-2 ]

Product Details of [ 1129-30-2 ]

Calculated chemistry of [ 1129-30-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1129-30-2 ]

Application In Synthesis of [ 1129-30-2 ]

[ 1129-30-2 ] Synthesis Path-Upstream 1~10

[ 1129-30-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1129-30-2 ]

Ketones

Related Parent Nucleus of [ 1129-30-2 ]

Pyridines

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 1129-30-2 ]

Related Parent Nucleus of
[ 1129-30-2 ]