[ CAS No. 142646-58-0 ] {[proInfo.proName]}

Name: 142646-58-0|4,4'-Dinonyl-2,2'-bipyridine|98%
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SKU: A173121
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Quality Control of [ 142646-58-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 142646-58-0 ]

SDS Specification

Alternatived Products of [ 142646-58-0 ]

Product Details of [ 142646-58-0 ]

CAS No. :	142646-58-0	MDL No. :	MFCD00800915
Formula :	C₂₈H₄₄N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHJFWJXYEWHCGD-UHFFFAOYSA-N
M.W :	408.66	Pubchem ID :	4285174
Synonyms :		Chemical Name :	4,4'-Dinonyl-2,2'-bipyridine

Calculated chemistry of [ 142646-58-0 ]

Physicochemical Properties

Num. heavy atoms :	30
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.64
Num. rotatable bonds :	17
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	134.31
TPSA :	25.78 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-1.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	6.16
Log Po/w (XLOGP3) :	10.66
Log Po/w (WLOGP) :	8.73
Log Po/w (MLOGP) :	5.15
Log Po/w (SILICOS-IT) :	9.68
Consensus Log Po/w :	8.08

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-8.26
Solubility :	0.00000223 mg/ml ; 0.0000000054 mol/l
Class :	Poorly soluble
Log S (Ali) :	-11.15
Solubility :	0.0000000029 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-11.33
Solubility :	0.0000000019 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	3.82

Safety of [ 142646-58-0 ]

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 [ 142646-58-0 ]

* 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 [ 142646-58-0 ]
Downstream synthetic route of [ 142646-58-0 ]

[ 142646-58-0 ] Synthesis Path-Upstream 1~2

1
[ 1134-35-6 ]
[ 111-83-1 ]
[ 142646-58-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With n-butyllithium; diisopropylamine In tetrahydrofuran at 0 - 20℃; for 15 h; Inert atmosphere	Diisopropylamine (28.0 mL, 0.160 mol, 2.66 equiv.) was dissolved in dry THF (60 mL) under an argon atmosphere. n-butylithium (107.0 mL, 0.160 mol, 2.66 equiv.) was added dropwise at 0 °C and the solution was stirred for 1 h. Afterwards, a solution of 4,4′-dimethyl-2,2′-bipyridine (11.0 g, 0.060 mol, 1 eq.) in dry THF (300 mL) was slowly added and the orange solution was stirred for 3 h. The reaction mixture was kept at 0 °C and bromooctane (28.0 mL, 0.160 mol, 2.66 equiv.) in dry THF (20 mL) was added. The reaction mixture was then allowed to warm to room temperature. After stirring for 12 h the reaction was quenched first with water (20 mL), then poured into an ice/ water mixture and extracted with diethylether. The resulting yellow oil was recrystallized from hexane, redissolved in DCM, extracted with diluted NaOH, dried over MgSO₄, filtered and the solvent removed in vacuo. Drying in high vacuum yielded the desired product (11.02 g, 0.027 mol, 45 percent). ¹H NMR (500 MHz, DMSO) δ in ppm= 8.85 (s, 1H), 8.83 (s, 1H), 7.28 (s, 1H), 7.27 (s, 1H), 2.68 (t, J= 7.6 Hz, 4H), 1.62 (p, J= 8.2, 6.9 Hz, 4H), 1.32–1.11 (m, 24H), 0.83 (t, J= 6.5 Hz, 6H). HRMS (ESI) m/z: [M+H]⁺ calcd. for (C₂₈H₄₄) 409.358; found 409.3581.

Reference： [1] Dyes and Pigments, 2014, vol. 104, p. 24 - 33
[2] Journal of the American Chemical Society, 1998, vol. 120, # 2, p. 305 - 316

2
[ 108-89-4 ]
[ 142646-58-0 ]

Reference： [1] Journal of the American Chemical Society, 1998, vol. 120, # 2, p. 305 - 316

[ 142646-58-0 ] Synthesis Path-Downstream 1~68

1
[ 1134-35-6 ]
[ 111-83-1 ]
[ 142646-58-0 ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: Synthesis was carried out using modified procedure [20]. Undernitrogen atmosphere a solution LDA (4.075 ml, 8.1 mmol), waschilled to a preset temperature of -75 C. This solution was stirredfor 15 min. A solution of 4,4'-dimethyl-2,2'-bipyridine (0.5 g,2.7 mmol in 10 ml THF) was added drop wise to LDA solution.The mixture was further magnetically stirred for another 90 minutes.A solution of 1-bromoalkane (5.9 mmol, 0.80 g for C5, 0.89 gfor C6, 0.97 for C7, 1.06 for C8, 1.11 g for C9) in 10 ml of THF wasadded drop wise to the reaction mixture. The resultant magneticallystirred reaction mixture was kept for 30 minutes at -75 Cand further slowly heated to temperature 26 C under nitrogenatmosphere. The yellow coloured solution after 12 h was pouredin 100 ml of millipore water and the organic layer was extractedin ethyl acetate and dried over anhydrous sodium sulphate. Theproduct was purified using column chromatography with ethylacetate in petroleum-ether. The yellow fraction was collected at10% ethyl acetate in petroleum ether and the solvent was reducedby rotary evaporator. The resulting off-white crystalline productwas recrystallized in petroleum ether subsequently and dried invacuum (Scheme 1).
45%	With n-butyllithium; diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 15h;Inert atmosphere;	Diisopropylamine (28.0 mL, 0.160 mol, 2.66 equiv.) was dissolved in dry THF (60 mL) under an argon atmosphere. n-butylithium (107.0 mL, 0.160 mol, 2.66 equiv.) was added dropwise at 0 C and the solution was stirred for 1 h. Afterwards, a solution of 4,4?-dimethyl-2,2?-bipyridine (11.0 g, 0.060 mol, 1 eq.) in dry THF (300 mL) was slowly added and the orange solution was stirred for 3 h. The reaction mixture was kept at 0 C and bromooctane (28.0 mL, 0.160 mol, 2.66 equiv.) in dry THF (20 mL) was added. The reaction mixture was then allowed to warm to room temperature. After stirring for 12 h the reaction was quenched first with water (20 mL), then poured into an ice/ water mixture and extracted with diethylether. The resulting yellow oil was recrystallized from hexane, redissolved in DCM, extracted with diluted NaOH, dried over MgSO4, filtered and the solvent removed in vacuo. Drying in high vacuum yielded the desired product (11.02 g, 0.027 mol, 45 %). 1H NMR (500 MHz, DMSO) delta in ppm= 8.85 (s, 1H), 8.83 (s, 1H), 7.28 (s, 1H), 7.27 (s, 1H), 2.68 (t, J= 7.6 Hz, 4H), 1.62 (p, J= 8.2, 6.9 Hz, 4H), 1.32-1.11 (m, 24H), 0.83 (t, J= 6.5 Hz, 6H). HRMS (ESI) m/z: [M+H]+ calcd. for (C28H44) 409.358; found 409.3581.

Reference： [1]Journal of the American Chemical Society,2019
[2]Polyhedron,2019,vol. 164,p. 96 - 107
[3]Dyes and Pigments,2014,vol. 104,p. 24 - 33
[4]Journal of the American Chemical Society,1998,vol. 120,p. 305 - 316

2
[ 108-89-4 ]
[ 142646-58-0 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 305 - 316

3
cobalt(II) perchlorate hexahydrate [ No CAS ]
[ 142646-58-0 ]
Co(4,4'-dinonyl-2,2'-dipyridyl)3(ClO₄)2 [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11215 - 11222

4
potassium cyanide [ No CAS ]
2NH₄⁽¹⁺⁾*Fe⁽²⁺⁾*2SO₄^(2-)*5H₂O = (NH₄)2Fe(SO₄)2*5H₂O [ No CAS ]
[ 142646-58-0 ]
cis-bis(4,4'-dinonyl-2,2'-bipyridine)dicyanoiron(II) [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1298 - 1299

5
platinum(II) cyanide [ No CAS ]
[ 142646-58-0 ]
[ 518299-68-8 ]

Reference： [1]Chemistry Letters,2008,vol. 37,p. 16 - 17

6
[ 10025-99-7 ]
[ 142646-58-0 ]
[ 518299-68-8 ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,2003,vol. 59,p. m25-m26
[2]Journal of Materials Chemistry C,2015,vol. 3,p. 734 - 741

7
ammonium hexafluorophosphate [ No CAS ]
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 142646-58-0 ]
bis(2-phenylpyridine-C⁽²⁾,N')(4,4'-di-n-nonyl-2,2'-bipyridine)iridium(III) hexafluorophosphate [ No CAS ]

Reference： [1]Organometallics,2004,vol. 23,p. 5856 - 5863

8
chloro(1,5-cyclooctadiene)rhodium(I) dimer [ No CAS ]
silver perchlorate [ No CAS ]
[ 142646-58-0 ]
[ 684239-49-4 ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 208 - 209

9
[ 26042-63-7 ]
[ 109994-19-6 ]
[ 142646-58-0 ]
[Pt(1,4,7-trithiacyclononane)(4,4'-dinonyl-2,2'-bipyridine)](PF₆)2 [ No CAS ]

Reference： [1]Polyhedron,2004,vol. 23,p. 1361 - 1369

10
di-μ-chlorobis{(2-phenylpyridine)palladium(II)} [ No CAS ]
[ 2923-28-6 ]
[ 142646-58-0 ]
[ 911849-88-2 ]

Reference： [1]Inorganic Chemistry Communications,2006,vol. 9,p. 93 - 95

11
di-μ-chlorobis{(7,7-benzoquinoline)palladium(II)} [ No CAS ]
[ 2923-28-6 ]
[ 142646-58-0 ]
[ 911849-99-5 ]

Reference： [1]Inorganic Chemistry Communications,2006,vol. 9,p. 93 - 95

12
[ 15226-74-1 ]
[ 3383-21-9 ]
[ 142646-58-0 ]
Co(III)(4,4'-dinonyl-2,2'-bipyridine)(3,5-di-tert-butylsemiquinonato)(3,5-di-tert-butylcatecholato) C₅₆H₈₄CoN₂O₄, K₁ [ No CAS ]

Reference： [1]Dalton Transactions,2006,vol. 6,p. 1377 - 1382

13
[ 56465-06-6 ]
[ 142646-58-0 ]
[3-CO-3,3-(κ2-4,4'-di-n-nonyl-2,2'-bipyridyl)-closo-3,1,2-RuC2B9H11] [ No CAS ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 370 - 385

14
[ 52462-29-0 ]
[ 174397-53-6 ]
[ 142646-58-0 ]
[Ru(4,4'-dinonyl-2,2'-bipyridine)(2,2'-bipyridne-4,4'-(PO₃H₂)2)2]Cl₂ [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 3320 - 3328

15
[ 52462-29-0 ]
[ 176220-38-5 ]
[ 142646-58-0 ]
[Ru(4,4'-dinonyl-2,2'-bipyridine)(2,2'-bipyridne-4,4'-(CH₂PO₃H₂)2)2]Cl₂ [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 3320 - 3328

16
Zn(1-phenyl-3-methyl-4-COCH₂C(CH₃)3-5-pyrazolonate)2 [ No CAS ]
[ 142646-58-0 ]
[ 1228769-47-8 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

17
Zn(1-phenyl-3-methyl-4-COC₆H₄C(CH₃)3-5-pyrazolonate)2 [ No CAS ]
[ 142646-58-0 ]
[ 1228769-45-6 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

18
[ 142646-58-0 ]
[ 7646-85-7 ]
[ 1228769-49-0 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

19
[ 6813-38-3 ]
[ 142646-58-0 ]
C₄₂H₅₂N₆O₄RuS₂⁽⁴⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 9Preparation of ?High-Quality Z907-Dye? Sensitizer[RuCl2(p-cymene)]2 was dissolved in DMF and 4,4'dinonyl 2,2' bipyridine then added. The reaction mixture was heated to 70-80 C. under nitrogen for 4 h with constant stirring. To this reaction flask 4,4'-carboxy-2,2'-bipyridine was added and the mixture refluxed at 170-180 C. for 4 h. Finally, excess of NH4NCS was added to the reaction mixture and the reflux at 180 C. continued for another 12 h.The reaction mixture was cooled down to room temperature and the solution was filtered (use the system without gummi-ring). The solvent was removed by using a rotary evaporator under vacuum. Water was added to the flask in order to remove excess of NH4SCN. The insoluble solid was collected on a sintered glass crucible by filtration. The solid was washed with water and diethyl ether.The solid was washed re-dissolved by adding 0.2 mM aq. NaOH and re-precipitated by slowly adding 0.1 mM aq. HNO3. The solid is isolated by filtration or centrifugation.The reaction was carried out under inert atmosphere (nitrogen) and exclusion of light. 1 (0.4 mmol) was dissolved in DMF (250 mL) and then 2 (0.8 mmol) was added (FIG. 9A). The mixture was stirred at 70-80 C. for 8 h. After adding 3 (0.8 mmol) the mixture was refluxed at 170-180 C. for 4 h. High excess (20-fold) of NH4NCS (16 mmol) was added to the reaction mixture and the reflux continued for another 8 h.

Reference： [1]Patent: US2010/275391,2010,A1 .Location in patent: Page/Page column 20

20
[ 37366-09-9 ]
[ 142646-58-0 ]
[ 1332307-95-5 ]

Reference： [1]Inorganic Chemistry,2011,vol. 50,p. 9714 - 9727

21
2BF₄⁽¹⁺⁾*C₈H₁₂N₄Pt⁽²⁺⁾ [ No CAS ]
[ 142646-58-0 ]
[Pt(4,4'-dinonyl-2,2'-dipyridyl)2][BF₄]2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	for 20h;Reflux;	Synthetic Procedure for [Pt(4,4'-dinonyl-2,2'-dipyridyl)2][BF2 The synthesis is carried out in accordance with a modified literature procedure (cf. A. Boixasse, J. Pons, X. Solans, M. Fontbardia, J. Ros, Inorg. Chim. Acta 2004, 357, 827).[PtCl2(CH3CN)2] (0.300 g, 0.862 mmol) is suspended in 50 ml of dry acetonitrile under N2. AgBF4 (0.336 g, 1.724 mmol) is added, and the reaction mixture is refluxed for 20 h. Precipitated AgCl is filtered off, and 4,4'-dinonyl-2,2'-dipyridyl (0.705 g, 1.724 mmol) is added to the clear, colourless solution. The mixture is then refluxed for a further 20 h. The precipitated solid (residues of AgCl) is filtered off, and the clear, pale-yellow reaction solution is concentrated in a rotary evaporator. The solution is placed in the freezer overnight, during which a beige solid precipitates out. The precipitate is filtered off with suction and washed with ethanol and ether, and subsequently dried. The solid is dissolved in dichloromethane and precipitated using ether. The fine, pale-green precipitate is filtered off and dried in a desiccator.Empirical formula: PtC56H88N4B2F8 (1185.67 g/mol)Elemental analysis: PtC56H88N4B2F8 (1185.67 g/mol)calculated: C 56.68, H 7.48, N 4.72found: C 56.68, H 7.16, N 4.56Mass spectrometry: ES-MS, m/e=506.0 M2+, 100%

Reference： [1]Patent: US2011/275818,2011,A1 .Location in patent: Page/Page column 26

22
[ 142646-58-0 ]
[ 1228769-33-2 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

23
[ 142646-58-0 ]
[ 1228769-35-4 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

24
[ 142646-58-0 ]
[ 1228769-41-2 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

25
[ 142646-58-0 ]
[ 1228769-43-4 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

26
[ 142646-58-0 ]
[ 1228769-39-8 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

27
[ 142646-58-0 ]
[ 1228769-37-6 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 4205 - 4212

28
ferrous ammonium sulphate [ No CAS ]
sodium perchlorate [ No CAS ]
[ 142646-58-0 ]
tris-4,4'-di-n-nonyl-2,2'-bipyridine iron(II) perchlorate [ No CAS ]

Reference： [1]Journal of the Electrochemical Society,2012,vol. 159,p. E69-E72

29
[ 52462-29-0 ]
[ 6813-38-3 ]
[ 142646-58-0 ]
C₅₂H₆₀N₆O₈Ru⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		0.3g (0.49mmol) of [Ru (p-cymene)2CI2]2 are added to 60 ml of DMF under nitrogen inert atmosphere at atmospheric pressure, to this solution 0,4g (0,98 mmol) of 4,4'-dinonyl-2,2'-pyridyl (dnbpy) are added and the resultant mixture is heated at 60C for 2h. Successively 0,24 g (0,98 mmol) of 4,4'-dicarboxy-2,2'-pyridyl (Hdcbpy2) are added and the reaction mixture is heated under reflux (160C) for 4h. 0.24g (0.98mmol) of Hdcbpy2 and 0.157g (3.9mmol) of NaOH are dissolved in 3ml of water and then added to reaction mixture then refluxed over further 2h.The reaction mixture is hot filtered and the solvent is removed under vacuum evaporation. Obtained solid is dissolved in basic NaOH solution and the product precipitated at pH = 2 by addition of aqueous HPF6 solution. The dissolution and precipitation procedures are repeated two times, the precipitate is washed with aqueous HPF6 solution and finally with ethyl ether. Yield 60%.The resulting product, without further purifications, is characterized by cyclic voltammetry (figure 20) and JV plot (figure 21) .Particularly, figure 20 shows cyclic voltammogramm of [cis-Ru (HDCBPy2)2(dnbpy)]2+ product obtained according to the conventional thermal synthesis under the following experimental conditions: electrolytic solution: L1CIO4 0.1N in acetonitrile, working electrode: glassy carbon, reference electrode: SCE.Figure 2 vshows DSSC JV plot for [cis-Ru (HDCBPy2)2 (dnbpy)]2+ dye obtained according to known art by thermal synthesis under following simulated experimental irradiation conditions (AM 1.5 75mW cm"2): Mediator/electrolyte: Co(DTB)3 (OTf)2 0.15M, Fe(DMB)3 (PF6)2 0,015M, Li (OTf) 0.5M in acetonitrile. (DTB = 4,4'-dimethyl-2,2'-bipyridyl, DMB = 4,4'- diterbutyl-2,2'-bipyridyl, OTf = p-toluenesulphonate). Cathode: potentiostatically (15s) electrocoated PEDOT (polyethylene dioxide thiophene) FTO. Transparent TiO2. Photovoltaic parameters corresponding to Figure 21 (Jsc, Voc, FF, e eta) are respectively: 2.56 mA cm"2 369 mV, 0.49 and 0.66%.

Reference： [1]Patent: WO2012/73268,2012,A1 .Location in patent: Page/Page column 16-17

30
cis-[Ru(dcbipy)₂Cl₂] [ No CAS ]
[ 142646-58-0 ]
C₅₂H₆₀N₆O₈Ru⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		100 mg (0.15mmol) of cis-dichlorobis ((4,4'-dicarboxy-2,2'-pyridyl) ruthenium (II), obtained using high pressure synthesis as reported in example 1 and 61.8mg (0.15mmol) of dnbpy suspended in 12ml of water are added to a reaction vessel (HP500) . The reactor temperature of the reactor has been increased at 180C under a pressure of approximately 200 PSI while the power of the reactor has been set at 800W. These conditions are maintained for a reaction time of 120 minutes. After cooling to room temp, obtained precipitated is separated by filtration through porous glass filter (G4), dissolved in basic water, filtered and precipitated by addition of HPF6 aqueous solution at about pH 2. 150mg (77% yield) of solid crystalline a red crystalline solid have been obtained. The obtained product, without further purification, is characterized by UV-vis spectroscopy (figure 16), 1H NMR (figure 17), as well as CV cyclic voltammetric (figure 18) and photoelectrochemical measures (JV plot in figure 19) .Particularly, figure 18 shows cyclilc voltammogramm for [cis-Ru (HDCBPy2)2 (dnbpy)]2+ product obtained using microwave reactor under high pressure water according to the following experimental conditions: electrolytic solution: UCIO4 0.1 N in acetonitrile, working electrode: glassy carbon, reference electrode: HgSO.j.Figure 19 shows DSSC JV plot for [cis-Ru (HDCBPy2)2(dnbpy)]2+ dye obtained according to the present invention by microwave synthesis (AM 1.5 (74mW cm"2) under following simulated experimental irradiation conditions (AM 1.5 (74mW cm"2): Mediator/electrolyte: Co(DTB)3(OTf)2 0.15M, Fe(DMB)3(PF6)2 0,015M, Li(OTf) 0.5M in acetonitrile. (DTB = 4,4'- dimethyl-2,2'-bipyridyl, DMB = 4,4'-diterbutyl-2,2'-bipyridyl, OTf = p- toluenesulphonate) . Cathode: potentiostatically (15s) electrocoated PEDOT (20") (polyethylene dioxide thiophene) FTO. Transparent Ti02. Photovoltaic parameters corresponding to Figure 19 (Jsc, Voc, FF, e eta) are respectively: 3.53 mA cm"2, 531 mV, 0,52 and 1.3%.

Reference： [1]Patent: WO2012/73268,2012,A1 .Location in patent: Page/Page column 15-16

31
hexafluorophosphoric acid [ No CAS ]
[RhCl₂(p-cymene)]2 [ No CAS ]
[ 6813-38-3 ]
[Ru(4,4'-dinonyl-2,2'-bipyridine)₂(2,2'-bibenzimidazolate)] [ No CAS ]
[ 142646-58-0 ]
[Ru(4,4'-dinonyl-2,2'-bipyridine)₂(2,2'-bibenzimidazolate)Ru(4,4'-dinonyl-2,2'-bipyridine)(2,2'-bipyridine-4,4'-dicarboxylic acid)](hexafluorophosphate)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.096 g		Under argon atmosphere, into a 200 mL three-necked flask were placed dichloro-p-cymene ruthenium dimer (0.200 g, 0.327 mmol), dnbpy (0.277 g, 0.657 mmol) and N,N-dimethylformamide (100 mL). After deaeration, the mixture was reacted at 60 C for 4 hours. [0124] The reaction solution was cooled down, and then H2dcbpy (0.160 g, 0.656 mmol) was added to the reaction solution. After re-deaeration, the mixture was reacted at 160 C for 4 hours. The reaction solution was cooled down, and then a 1 mol/L sodium hydroxide aqueous solution (1.34 mL) and [Ru(dnbpy)2(BiBzIm)] (0.678 g, 0.589 mmol) were added to the reaction solution, and the mixture was refluxed and reacted for 2 hours. [0125] The resultant reaction solution was concentrated under reduced pressure. The resultant concentrate was dissolved in methanol, and then the resultant solution was subjected to liquid chromatography (developing solvent: methanol (containing 0.2 vol% of formic acid)) for fractionation, to collect the fraction containing a desired complex. The fraction was concentrated under reduced pressure. The resultant concentrate was dissolved in methanol (2.5 mL), and then a hexafluorophosphoric acid aqueous solution at pH 2 (2.5 mL) was added to the solution. And then, the precipitate was collected by filtration, to provide the binuclear ruthenium complex dye (C3) (0.096 g).

Reference： [1]Patent: EP2548926,2013,A1 .Location in patent: Paragraph 0123-0127

32
[Ru(1,10-phenanthroline)₂(2,2'-bibenzimidazolate)] [ No CAS ]
hexafluorophosphoric acid [ No CAS ]
[RhCl₂(p-cymene)]2 [ No CAS ]
[ 6813-38-3 ]
[ 142646-58-0 ]
[Ru(1,10-phenanthroline)₂(2,2'-bibenzimidazolate)Ru(4,4'-dinonyl-2,2'-bipyridine)(2,2'-bipyridine-4,4'-dicarboxylic acid)](hexafluorophosphate)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.104 g		Under argon atmosphere, into a 100 mL three-necked flask were placed dichloro-p-cymene ruthenium dimer (0.100 g, 0.164 mmol), dnbpy(0.139 g, 0.329 mmol) and N,N-dimethylformamide (50 mL). After deaeration, the mixture was reacted at 60 C for 4 hours. [0118] The reaction solution was cooled down, and then H2dcbpy (0.080 g, 0.328 mmol) was added to the reaction solution. After re-deaeration, the mixture was reacted at 160 C for 4 hours. The reaction solution was cooled down, and then a 1 mol/L sodium hydroxide aqueous solution (0.67 mL) and [Ru(phen)2(BiBzIm)] (0.207 g, 0.298 mmol) were added to the reaction solution, and the mixture was refluxed and reacted for 5.5 hours. [0119] The resultant reaction solution was concentrated under reduced pressure. The resultant concentrate was dissolved in methanol (30 mL), and then a hexafluorophosphoric acid aqueous solution at pH 2 (8 mL) was added to the solution, and the precipitate was separated by filtration. [0120] Subsequently, a hexafluorophosphoric acid aqueous solution at pH 2 (16.5 mL) was added to the filtrate, and the precipitate was collected by filtration. The collected precipitate was dried, and then dissolved in methanol, and then the resultant solution was subjected to liquid chromatography (developing solvent: methanol (containing 0.2 vol% of formic acid)) for fractionation, to collect the fraction containing a desired complex. The fraction was concentrated under reduced pressure. The resultant concentrate was dissolved in methanol (10 mL), and then a hexafluorophosphoric acid aqueous solution at pH 2 (10 mL) was added to the solution. And then, the precipitate was collected by filtration, to provide the binuclear ruthenium complex dye (C2) (0.104 g).

Reference： [1]Patent: EP2548926,2013,A1 .Location in patent: Paragraph 0117-0122

33
zinc tetrafluoroborate [ No CAS ]
[ 142646-58-0 ]
C₂₈H₄₄N₂*Zn⁽²⁺⁾*2BF₄^(1-) [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 9679 - 9687

34
zinc(II) sulfate heptahydrate [ No CAS ]
[ 7732-18-5 ]
[ 142646-58-0 ]
2C₂₈H₄₄N₂*2Zn⁽²⁺⁾*2O₄S^(2-)*2H₂O [ No CAS ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 9679 - 9687

35
[ 52462-29-0 ]
[ 142646-58-0 ]
[ 880067-02-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To Dichloro-p-cymene ruthenium dimer (0.050 g, 0.090 mmol, 1.00 equiv.) dissolved in dry, degassed DMF (20 mL), under argon, and shielded from light was added donor ligand dnbpy 10 (0.073 g, 0.180 mmol, 2.00 equiv.). The mixture was stirred at 75 C for 5 h, cooled to room temperature, and stirred for 12 h. After adding dpbpy 7 (0.150 g, 0.360 mmol, 4 equiv.) the reaction mixture was refluxed for 4 h resulting in a dark-red solution. The solvent was removed in vacuo and the crude product purified by size exclusion chromatography on a Sephadex LH-20 column using water. Aqueous HCl (6 M, 25 mL) was added to the main fraction and the resulting solution was refluxed for 15 h. The black solution was purified by size exclusion chromatography on a Sephadex LH-20 yielding 4 (40.0 mg, 0.045 mmol, 28.0 %).
	In methanol;	General procedure: All compounds were synthesized using a similar procedure.[(h6-p-cymene)RuCl2]2 (e.g. 150 mg, 0.245 mmol) was dissolved in25e30 ml methanol and a calculated stoichiometric amount ofligand was added neat. After stirring for a minimum of 0.5 h (oruntil all ligand has dissolved) at ambient temperature the solventwas removed under vacuum on a rotary evaporator. The residuewas washed and stirred repeatedly with Et2O and each Et2O washphase was carefully decanted from the readily settling and insolubleproduct. The final product was dried under vacuum at RT e40 C; in all cases yields were 90%. Complexes Characterisationdata for individual complexes are reported in the following.

Reference： [1]Dyes and Pigments,2014,vol. 104,p. 24 - 33
[2]Journal of Organometallic Chemistry,2016,vol. 823,p. 136 - 146

36
[ 14099-01-5 ]
[ 142646-58-0 ]
[ 1563017-96-8 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 2606 - 2612

37
ammonium hexafluorophosphate [ No CAS ]
C₅₂H₃₄Cl₂N₄Rh₂ [ No CAS ]
[ 142646-58-0 ]
C₅₄H₆₀IrN₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 9178 - 9182,5
Angew. Chem.,2014,vol. 126,p. 9544,1
Angewandte Chemie,2014,vol. 126,p. 9544,1

38
(tetra-n-butylammonium)₂[Mo₃S₇Br₆] [ No CAS ]
[ 142646-58-0 ]
Mo₃S₇Br₄(4,4’-dinonyl-2,2’-bipyridine) [ No CAS ]

Reference： [1]ChemSusChem,2015,vol. 8,p. 148 - 157

39
[ 52462-29-0 ]
[ 142646-58-0 ]
dichloro(p-cymene)-4,4′-dinonyl-2,2′-bipyridine ruthenium(II) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; for 4h;Reflux;	Example 2 Synthesis of Ruthenium Complex K23 (0113) The complex K23 was synthesized by refluxing a mixture of 4,4?-dinonyl-2,2?-bipyridine (150 mg, 0.37 mmol) and dichloro(p-cymene)ruthenium(II) dimer (113 mg, 0.18 mmol) in argon degassed absolute ethanol (40 mL) for 4 h. Evaporation of the solvent leaded to dichloro(p-cymene)-4,4?-dinonyl-2,2?-bipyridine-ruthenium(II) complex as a brow-yellow oil in a quantitative yield. This intermediate complex was used without further purification for reacting with 4,4?-dicarboxy(phenylethenyl)-2,2?-bipyridine (0.36 mmol) in dry and argon degassed DMF (30 mL). The mixture was heated at 150 C. for 4 h and to the resulting dark purple solution was added NH4NCS (408 mg, 5.4 mmol) and the mixture heated at 150 C. for 4 h more. After evaporation of the DMF, the resulting purple residue was suspended in water (200 mL) and sonicated for 5 min. The pH was adjusted to 3 with HNO3 (0.02 M) and the mixture was let stand in the fridge overnight. The crude complex was dissolved in methanol containing two equivalents of tetrabutylammonium hydroxide. The concentrated solution was filtered through a sintered glass crucible and charged onto a LH-20 Sephadex column, which was prepared in methanol. The adsorbed complex was eluted using methanol as an eluent. The main band was collected and the solution pH was lowered to 3 using 0.02 M HNO3 acid. The precipitated complex was collected on a glass fit and air-dried. Yield 60 mg, 32%. The analytical and spectroscopic data are consistent with the structures shown in FIG. 2.

Reference： [1]Patent: US8962977,2015,B2 .Location in patent: Page/Page column 15

40
(tetraethylammonium)₄[(Nb₂S₄)(isothiocyanate)₈] [ No CAS ]
[ 142646-58-0 ]
(tetraethylammonium)₂[(Nb₂S₄)(isothiocyanate)₆(di-(4,4'-nonyl)-2,2'-bipyridine)] [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2015,vol. 2015,p. 2865 - 2874

41
bis[μ-chloro-bis(2-phenylisoquinolinato-C²,N)iridium(III)] [ No CAS ]
ammonium hexafluorophosphate [ No CAS ]
[ 142646-58-0 ]
4,4'-dinonyl-2,2'-bipyridinebis(1-phenylisoquinoline)iridium(III) hexafluorophosphate [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 16033 - 16036
[2]Inorganic Chemistry,2018,vol. 57,p. 14023 - 14026

42
ruthenium(III) chloride trihydrate [ No CAS ]
[ 142646-58-0 ]
[ 299898-96-7 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 41165 - 41172

43
bis[2-(2,4-difluorophenyl)pyridinato-N,C₆']iridium(III) chloride dimer [ No CAS ]
ammonium hexafluorophosphate [ No CAS ]
[ 142646-58-0 ]
[Ir(4,4'-dinonyl-2,2'-bipyridine)(2-(2,4-difluorophenyl)pyridine)₂](PF₆) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4026 - 4031

44
ammonium hexafluorophosphate [ No CAS ]
chloro(1-phenylpyrazole)iridium(III) dimer [ No CAS ]
[ 142646-58-0 ]
[Ir(4,4'-dinonyl-2,2'-bipyridine)(1-phenyl-1H-pyrazole)₂](PF₆) [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4026 - 4031

45
ruthenium(III) chloride trihydrate [ No CAS ]
[ 6813-38-3 ]
ammonium thiocyanate [ No CAS ]
[ 142646-58-0 ]
[ 502693-09-6 ]

Yield	Reaction Conditions	Operation in experiment
61%		0.851 g of ruthenium (III) chloride hydrate and 40 ml ofN-methylpyrrolidone were added to the first reactor and (4,4'-dinonyl-2,2'bipyridine)was added thereto while stirring and the mixture was stirred for 0.5 hour. In the second reactor, ligand 2(2,2'-bipyridine-4,4'-dicarboxylicacid) and 60 ml of N-methylpyrrolidone were placed and maintained at 140 to 150 C. The mixed solution of the first reactor was added to the secondreactor, stirring was continued for 1.5 hours while maintaining the temperatureat 140 to 150 C, and ammonium thiocyanate 5.16 g was added and stirred for 1hour and then the reactor was cooled. The reaction mixture was poured into distilled water toprecipitate a solid. The solid was dissolved in 40 ml of methanol and NaOH wereused to maintain the pH of 10 to 11. After purification by column usingSephadex resin, the solution was adjusted to pH 4.8 with nitric acid to give togive the desired compound as a solid.

Reference： [1]Patent: KR101569098,2015,B1 .Location in patent: Paragraph 0054-0057

46
[ 52462-29-0 ]
[ 6813-38-3 ]
ammonium thiocyanate [ No CAS ]
[ 142646-58-0 ]
[ 502693-09-6 ]

Yield	Reaction Conditions	Operation in experiment
28%		General procedure: 0.851 g of ruthenium (III) chloride hydrate and 40 ml of N-methylpyrrolidone were added to the first reactor(4,4'-dinonyl-2,2'bipyridine) was added thereto while stirring and the mixture was stirred for 0.5 hour. In the second reactor, ligand 2(2,2'-bipyridine-4,4'-dicarboxylic acid) and 60 ml of N-methylpyrrolidone were placed and maintained at 140 to 150 C. The mixed solution of the first reactor was added to the second reactor,Stirring was continued for 1.5 hours while maintaining the temperature at 140 to 150 C, and ammonium thiocyanate5.16 g was added and stirred for 1 hour and then the reactor was cooled. The reaction mixture was poured into distilled water to precipitate a solid. The solid was dissolved in methanol40 ml and NaOH were used to maintain the pH of 10 to 11, After purification by column using Sephadex resin,the solution was adjusted to pH 4.8 with nitric acid to give a solid to give the desired compound. Instead of ruthenium (III) chloride hydrate, [RuCl2 (p-cymene)] 2 Except that the complex compound was used, a heteroleptic ruthenium complex dye was synthesized in the same manner.

Reference： [1]Patent: KR101569098,2015,B1 .Location in patent: Paragraph 0055-0057; 0068-0069

47
[Mo₃S₄(thiourea)₈(H₂O)]Cl₄.4H₂O [ No CAS ]
[ 142646-58-0 ]
[Mo₃S₄Cl₃(4,4'-dinonyl-2,2'-bipyridine)₃]Cl [ No CAS ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 1128 - 1134

48
[ 17084-13-8 ]
[{Rh(μ-Cl)(2-(p-tolyl)pyridinato)2}2] [ No CAS ]
[ 142646-58-0 ]
C₅₂H₆₄N₄Rh⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.9%		General procedure: To a solution of [{M(mu-Cl)(ptpy)2}2] (M=Rh, Ir) (0.15mmol) in 25mL of a mixture of CH2Cl2/MeOH/H2O (1:1:0.5) the bipyridine ligand (0.3mmol) was added and the mixture refluxed with stirring for 3h. After cooling to room temperature KPF6 (0.5mmol) was added and stirred for 20min. The solvent was removed to dryness in vacuo and the residue dissolved in dichloromethane and chromatographed on alumina with CH2Cl2/acetone (9:1) as the eluent. The resulting solution was evaporated to dryness and the residue was redissolved in 5ml of dichloromethane and the product was precipitated by slow diffusion of isohexane. 2.11 [Rh(ptpy)2(4,4'-Non2-bpy)]PF6 (9) Yield: 110?mg (0.11?mmol, 36.9%). Anal. Calc. for C52H64N4F6PRh: C, 62.90; H, 6.50; N, 5.64. Found: C, 62.94; H, 6.60; N, 5.95%. MS (FAB+): m/z?=?847.6 [M+] complex cation. 1H NMR: delta= 8.20 (s, 2H, H3'), 7.92-7.87 (m, 4H, H3?+?H6'), 7.83 (td, J?=?8.0, 1.5?Hz, 2H, H4), 7.67 (d, J?=?7.9?Hz, 2H, H8), 7.46-7.42 (m, 2H, H6), 7.25 (dd, J?=?5.5, 1.5?Hz, 2H, H5'), 6.99 (ddd, J?=?7.3, 5.8, 1.4?Hz, 2H, H5), 6.96-6.92 (m, 2H, H9), 6.12 (s, 2H, H11), 2.80 (m, 4H, Hnon), 2.13 (s, 6H, H13), 1.70 (p, J?=?7.8?Hz, 4H, Hnon), 1.45-1.20 (m, 24H, Hnon), 0.93-0.84 (m, 6H, Hnon). 13C NMR: delta?=?168.1 (d, JRhC?=?32?Hz, C12), 165.7 (C2), 157.1 (C2'), 154.8 (C4'), 150.3 (C6'), 149.0 (C6), 141.5 (C10), 141.3 (d, JRhC?=?1.5?Hz, C7), 138.6 (C4), 133.9 (C11), 128.1 (C5'), 125.0 (C8), 124.1 (C3'+C9), 123.2 (C5), 120.1 (C3), 36.1/32.4/30.7/30.0/29.9/29.84/29.82/23.2 (Cnon), 22.2 (C13), 14.4 (Cnon).

Reference： [1]Inorganica Chimica Acta,2018,vol. 471,p. 265 - 271

49
[ 17084-13-8 ]
[{Ir(μ-Cl)(2-(p-tolyl)pyridinato)2}2] [ No CAS ]
[ 142646-58-0 ]
C₅₂H₆₄IrN₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37.0%		General procedure: To a solution of [{M(mu-Cl)(ptpy)2}2] (M=Rh, Ir) (0.15mmol) in 25mL of a mixture of CH2Cl2/MeOH/H2O (1:1:0.5) the bipyridine ligand (0.3mmol) was added and the mixture refluxed with stirring for 3h. After cooling to room temperature KPF6 (0.5mmol) was added and stirred for 20min. The solvent was removed to dryness in vacuo and the residue dissolved in dichloromethane and chromatographed on alumina with CH2Cl2/acetone (9:1) as the eluent. The resulting solution was evaporated to dryness and the residue was redissolved in 5ml of dichloromethane and the product was precipitated by slow diffusion of isohexane. [2.12 [Ir(ptpy)2(4,4'-Non2-bpy)]PF6 (10) Yield: 120?mg (0.11?mmol, 37.0%). Anal. Calc. for C52H64N4F6PIr: C, 57.71; H, 5.96; N, 5.18. Found: C, 57.46; H, 6.01; N, 5.17%. MS (FAB+): m/z?=?937.4 [M+] complex cation. 1H NMR : delta= 8.22 (s, 2H, H3'), 7.90 (d, J?=?8.0?Hz, 2H, H3), 7.86 (d, J?=?5.6?Hz, 2H, H6'), 7.75 (td, J?=?8.0, 1.5?Hz, 2H, H4), 7.63 (d, J?=?8.0?Hz, 2H, H8), 7.47-7.44 (m, 2H, H6), 7.25 (dd, J?=?5.7, 1.6?Hz, 2H, H5'), 6.94 (ddd, J?=?7.3, 5.9, 1.4?Hz, 2H, H5), 6.92-6.87 (m, 2H, H9), 6.11 (s, 2H, H11), 2.83 (m, 4H, Hnon), 2.14 (s, 6H, H13), 1.70 (p, J?=?7.7?Hz, 4H, Hnon), 1.44-1.20 (m, 24H, Hnon), 0.92-0.84 (m, 6H, Hnon). 13C NMR: delta?=?168.5 (C2), 156.9/156.1 (C2'?+?C4'), 151.2 (C6'), 150.8 (C6), 148.9 (C12), 141.6 (C10?+?C7), 138.4 (C4), 132.9 (C11), 128.7 (C5'), 125.3 (C8), 124.8 (C3'), 124.1 (C9), 123.1 (C5), 120.0 (C3), 36.1/32.4/30.7/30.0/29.9/29.85/29.82 (Cnon), 22.1 (C13), 14.4 (Cnon).

Reference： [1]Inorganica Chimica Acta,2018,vol. 471,p. 265 - 271

50
ruthenium trichloride [ No CAS ]
[ 142646-58-0 ]
cis-[Ru(4,4'-dinonyl-2,2'-bipyiridine)₂Cl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		RuCl3 (188mg, 0.91mmol) was dissolved in EtOH/12 H2O (2:1) and the mixture was refluxed under nitrogen for four hours. After the solution turned blue, 4,4?-dinonyl-2,2?-bipyridine (800mg, 1.96mmol) in 10mL EtOH along with HCl (2 mL) were added while the ruthenium blue was still hot and the reflux was continued until the color of the solution changed to dark brown, after which a brown solid appeared. The solution was let to cool and the deep brown solid was separated by filtration and washed with water several times. The solid was then suspended in 2M 14 HCl (30mL) followed by the addition of 56 SnCl2·2H2O (0.06g, 0.26mmol). The mixture was heated for one hour until a dark precipitation appeared, which was collected by filtration, washed with water, and dried. The purification of the material was conducted by column chromatography on silica gel with 10% MeOH in acetone, affording 9 2 in 60% yield. 1H NMR (500MHz, CD3CN): 0.86 (12H, m), 1.30 (48H, m), 1.68 (8H, quint, J=7.5Hz), 2.78 (8H, t, J=7.7Hz), 7.20 (4H, dd, J=1.7Hz, 5.9Hz), 7.51 (4H, d, J=5.8Hz), 8.33 (4H, d, J=1.2Hz).

Reference： [1]Inorganica Chimica Acta,2018,vol. 471,p. 467 - 474

51
ammonium hexafluorophosphate [ No CAS ]
potassium hexachloroosmate(IV) [ No CAS ]
[ 142646-58-0 ]
(Os(II)(4,4'-dinonyl-2,2'-bipyridine)3)(PF6)2 [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 10757 - 10760

52
ammonium hexafluorophosphate [ No CAS ]
[Ru(cymene)(bis-4,4′-(trimethylaminomethyl)-2,2′-bipyridine)(Cl)]³⁺*Cl^-*2PF6^- [ No CAS ]
[ 142646-58-0 ]
[Ru(4,4′-nonyl-2,2′-bipyridine)₂(bis-4,4′-(trimethylaminomethyl)-2,2′-bipyridine)]⁴⁺*4PF₆⁻ [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 12232 - 12244

53
[ 52462-29-0 ]
C₂₆H₂₀N₂O₄ [ No CAS ]
[ 333-20-0 ]
[ 142646-58-0 ]
C₅₆H₆₄N₆O₄RuS₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2018,vol. 6,p. 9445 - 9452

54
[ 52462-29-0 ]
C₂₆H₁₈F₂N₂O₄ [ No CAS ]
[ 333-20-0 ]
[ 142646-58-0 ]
C₅₆H₆₂F₂N₆O₄RuS₂ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2018,vol. 6,p. 9445 - 9452

55
[ 52462-29-0 ]
[ 1762-42-1 ]
[ 1147550-11-5 ]
[ 142646-58-0 ]
C₄₆H₆₀N₆O₄RuS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.72 g		Step A)0.31 g of p-cymene dichloride dimer,0.41g<strong>[142646-58-0]4,4'-dinonyl-2,2'-bipyridine</strong>And 50 mL of N,N-dimethylformamide was placed in a three-necked flask, and the solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 80.C, reaction for 4 hours. Then cooled to room temperature;Step B)0.30 g was added to the three-necked flask after the reaction in the step A)2,2'-bipyridyl-4,4'-dicarboxylic acid diethyl ester,The solution was stirred for 15 minutes in an atmosphere of light and Ar gas, and then heated to 130 C for 5 hours.Then cooled to room temperature;Step C)0.97 g of NH4NCS was added to the three-necked flask after the reaction in the step B), in the dark and Ar gas atmosphere,After the solution was stirred for 15 minutes, it was heated to 120 C and reacted for 4 hours. After cooling to room temperature,The N,N-dimethylformamide was evaporated to dryness on a rotary evaporator. Add 150 mL of water to the remaining liquid.It was extracted three times with 150 mL of chloroform, and the obtained chloroform solution was washed three times with water, and then dried over anhydrous magnesium sulfate.After filtering, the filtrate is distilled off with a rotary evaporator, and the obtained solid is dried.Obtaining 1.08 g of the esterified product of Z907, the purity is 81.9%;Step D)1.08 g of the esterified product of Z991 obtained in step C) was dissolved in ethyl acetate.The mixture was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane.The collected product solution, distilled off the solvent, and dried.Obtaining 0.72 g of the esterified product of Z907, the purity is 96.2%;

Reference： [1]Patent: CN104447882,2018,B .Location in patent: Paragraph 0147; 0149-0156

56
cobalt(II) chloride hexahydrate [ No CAS ]
[ 90076-65-6 ]
[ 142646-58-0 ]
tris(4,4'-dinonyl-2,2'-bipyridine)cobalt (II) di(bis(trifluoromethane)sulfonimide) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 13935 - 13944

57
ammonium hexafluorophosphate [ No CAS ]
[ 33915-80-9 ]
[ 142646-58-0 ]
C₅₀H₆₀N₄Rh⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 14023 - 14026

58
ammonium hexafluorophosphate [ No CAS ]
C₆₀H₄₀Cl₂N₄Rh₂ [ No CAS ]
[ 142646-58-0 ]
C₅₈H₆₄N₄Rh⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 14023 - 14026

59
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
ammonium hexafluorophosphate [ No CAS ]
[ 142646-58-0 ]
C₅₀H₆₀IrN₄⁽¹⁺⁾*F₆P^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 14023 - 14026

60
[ 155475-93-7 ]
[ 142646-58-0 ]
[Pt(2-phenylpyridinato)(4,4'-bis(nonyl)-2,2'-bipyridine)]ClO₄ [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 1294 - 1301

61
ammonium hexafluorophosphate [ No CAS ]
rhodium(III) chloride hydrate [ No CAS ]
[ 142646-58-0 ]
C₈₄H₁₃₂N₆Ru⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: To a sonicated solution of ruthenium trichloride hydrate (0.1 g,0.48 mmol) in 5 ml anhydrous ethanol, a solution of 4,4'-dialkyl-2,2'-bipyridine (1.44 mmol in 10 ml absolute ethanol (0.394 g ofC5 for RC5, 0.434 g of C6 for RC6, 0.469 g of C7 for RC7, 0.506 gof C8 for RC8, 0.543 g of C9 for RC9) was added drop wise. Thereaction mixture was refluxed for 2 hr at 80 C. The resultingorange coloured solution was cooled at room temperature (26 C)and the solvent was reduced by rotatary evaporator. The pure productwas separated by silica gel column chromatography using 1:1ethyl acetate/petroleum ether as eluent solvent. The unreactedligands eluted as a first fraction (monitored by TLC) followed byorange band of the main product. The orange band was concentratedby reducing the solvent and further precipitated using2 ml saturated ammonium hexafluorophosphate solution inmethanol. The dark orange coloured precipitate was filtered andthe residue was washed with millipore water. The precipitatewas dried in vacuum (Scheme 2).

Reference： [1]Polyhedron,2019,vol. 164,p. 96 - 107

62
[iridium(III)(μ-chloro)(2-phenylpyridine)2]2 [ No CAS ]
[ 142646-58-0 ]
mer-bis[2-phenylpyridinato-C²,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 4962 - 4971

63
tetrakis(2-phenylquinoline-C2,N')(μ-dichloro)diiridium(III) [ No CAS ]
[ 142646-58-0 ]
mer-bis[2-phenylquinolinato-C²,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 4962 - 4971

64
bis[2-(2,4-difluorophenyl)pyridinato-N,C₆']iridium(III) chloride dimer [ No CAS ]
[ 142646-58-0 ]
mer-bis[2-(4,6-difluorophenyl)pyridinato-C²,N](4,4'-dinonyl-2,2'-bipyridine)iridium(III) chloride [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 4962 - 4971

65
[ 1210397-31-1 ]
[ 142646-58-0 ]
[Ru(2,6-bis(1-methyl-1H-benzo[d]imidazol-2-yl)pyridine)(4,4'-dinanyl-2,2'-bipyridine)Cl]Cl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019

66
[ 174476-70-1 ]
[ 142646-58-0 ]
[Ru((C₉H₁₉)₂-bpy)(4,4'-(PO(OEt)₂)₂-bpy)2]Cl₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019

67
8CH₄N₂S*4Cl^(1-)*3H₂O*3W⁽⁴⁺⁾*4S^(2-) [ No CAS ]
[ 142646-58-0 ]
[W₃S₄Cl₃(4,4′-di-n-nonyl-2,2′-bipyridine)₃]Cl [ No CAS ]

Reference： [1]Journal of Physical Chemistry B,2019,vol. 123,p. 8829 - 8837

68
bis(1,10-phenanthroline)dichlororuthenium(II) [ No CAS ]
ammonium hexafluorophosphate [ No CAS ]
[ 142646-58-0 ]
C₅₂H₆₀N₆Ru⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

Reference： [1]International Journal of Molecular Sciences,2019,vol. 20

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
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.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
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:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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:
P333	If skin irritation or rash occurs:
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
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 142646-58-0 ] {[proInfo.proName]}

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[ 142646-58-0 ] Synthesis Path-Upstream 1~2

[ 142646-58-0 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

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