Name: 1287-13-4|Bis(cyclopentadienyl)ruthenium(II)|99+%
Brand: Ambeed
SKU: A1233053
Price: 20.0 USD
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1
ruthenium trichloride [ No CAS ]
[ 542-92-7 ]
[ 1287-13-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With zinc; In ethanol; at -60 - 10℃; for 26h;	In a separable flask, 528 g (8 moles) of cyclopentadiene and 130 g (2 moles) of zinc powder of 200 meshes were put in 1500 ml of ethyl alcohol as an alcohol solvent, cooled to -60 C. and mixed by stirring. On the other hand, in a step separate from this step, a ruthenium chloride solution was prepared by dissolving 262 g (1 mole) of ruthenium chloride trihydrate (RuCl3.3H2O) in 500 ml of ethyl alcohol at room temperature. And the ruthenium chloride solution was added dropwise at a rate of 250 ml/l (one drop/hour) for 2 hours during stirring, with the temperature of a mixed solution of ethyl cyclopentadiene and zinc powder kept at not more than -10 C. Because an intense exothermic reaction occurs during the dropwise addition of the ruthenium chloride solution, care should be used so that the solution temperature does not exceed -10 C. during the dropwise addition of the solution. And after all the solution was added dropwise, a reaction was caused to occur for 24 hours with the solution temperature kept at 10 C. The mixing ratio of the raw materials on this occasion was ruthenium chloride: cyclopentadiene: zinc=1:8:2. After the reaction, it was ascertained that the solution discolored from blue to reddish brown and then the reaction solution was filtered. On this occasion, the zinc powder and the greater part of a synthesized bis(cyclopentadienyl)ruthenium are separated on filter paper. On the other hand, the bis(cyclopentadienyl)ruthenium is dissolved in the filtrate, though in small amount. Therefore, the filtrate was concentrated with an evaporator at 60 C. and at 1.3×104 Pa and then refiltered. Solid left after filtration obtained by this refiltration were rinsed with 500 ml of ethanol to remove organic impurities and further rinsed with 500 ml of water to remove inorganic impurities. These solid left after filtration were collected and dried at 25 C. under reduced pressure at 1.3×102 Pa. The dried solid left after filtration was refined under reduced pressure by the sublimation method. This purification step was performed by use of a sublimation apparatus as shown in FIG. 1. In this sublimation apparatus, the solid left after filtration (constituted by a bis(cyclopentadienyl)ruthenium, zinc powder, nonvolatile impurities, etc.) on the bottom of a flask under reduced pressure is heated in an oil bath thereby to sublime the bis(cyclopentadienyl)ruthenium. In order that the sublimed bis(cyclopentadienyl)ruthenium is cooled by water-cooled umbrellas and recrystallizes, the umbrellas are taken out and the adhering bis(cyclopentadienyl)ruthenium is recovered. For the purification conditions used, the heating temperature was 110 C. and the pressure was 13.3 Pa. The amount of the bis(cyclopentadienyl)ruthenium produced at that time was 220 g and the yield was 95%. When the bis(cyclopentadienyl)ruthenium produced in this embodiment was analyzed by TG/DTA (thermogravimetric/differential thermal analysis), results as shown in FIG. 2 were obtained. From the analysis results it was ascertained that the bis(cyclopentadienyl)ruthenium produced in this embodiment has a purity of 99.99% and does not contain nonvolatile impurities.
73.5%	With zinc; at 20℃; for 1h;	In a flask in which the atmosphere had been replaced with nitrogen, 119.6 g (0.457 mole) of ruthenium chloride was dissolved in 2500 ml of ethyl alcohol and then 1158 g (17.55 moles) of cyclopentadiene and 163 g (2.49 moles) of zinc powder were added to this solution at a time. And this mixed solution was stirred at room temperature for 1 hour and a reaction was caused to occur. A deposit after the reaction was filtered and hot toluene was caused to pass through filter paper. Next, a filtrate was concentrated to 500 ml under reduced pressure by use of a rotary evaporator and the concentrate was caused to pass through an alumina column by using hexane and ethyl acetate as solvents, whereby a bis(cyclopentadienyl)ruthenium was separated. The separated liquid was concentrated by use of a rotary evaporator and the concentrate was dried at 25 C. in a vacuum of 1.3×102 Pa, whereby bis(ethyl cyclopentadienyl)ruthenium was obtained. The amount of the bis(cyclopentadienyl)ruthenium produced at that time was 84.36 g and the yield was 73.5. When this produced bis(ethyl cyclopentadienyl)ruthenium was analyzed, it was found that its purity was 94.5%-a low purity.

Reference： [1]Patent: US2004/260109,2004,A1 .Location in patent: Page/Page column 4
[2]Patent: US2004/260109,2004,A1 .Location in patent: Page/Page column 4

2
[ 1287-13-4 ]
[ 7440-18-8 ]

Reference： [1]Journal of Physical Chemistry A,1999,vol. 103,p. 2659 - 2663
[2]Inorganic Chemistry,1964,vol. 3,p. 1057 - 1058
[3]Electrochimica Acta,2009,vol. 54,p. 5262 - 5266
[4]Journal of the Electrochemical Society,2010,vol. 157,p. K10-K14
[5]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 200, page 536 - 539
[6]Applied Physics Letters,,p. 1 - 3
Applied Physics Letters,2005,vol. 86

3
[ 14284-93-6 ]
[ 17306-10-4 ]
[ 1287-13-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6146 - 6147
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 199, page 533 - 536

4
ruthenium(III) chloride trihydrate [ No CAS ]
[ 1287-13-4 ]

Reference： [1]Inorganic Chemistry,1993,vol. 32,p. 3654 - 3659

5
ruthenium(III) chloride trihydrate [ No CAS ]
[ 1287-13-4 ]
(trimethylsilyl)ruthenocene [ No CAS ]

Reference： [1]Inorganic Chemistry,1993,vol. 32,p. 3654 - 3659

6
ruthenium(III) chloride trihydrate [ No CAS ]
[ 542-92-7 ]
[ 1287-13-4 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1980,p. 1961 - 1964

7
ruthenium(III) chloride trihydrate [ No CAS ]
[ 29942-99-2 ]
[ 1287-13-4 ]

Reference： [1]Inorganic Chemistry,1993,vol. 32,p. 3654 - 3659
[2]Inorganic Chemistry,1993,vol. 32,p. 3654 - 3659

8
ruthenium(III) chloride trihydrate [ No CAS ]
[ 33630-76-1 ]
[ 1287-13-4 ]

Reference： [1]Inorganic Chemistry,1993,vol. 32,p. 3654 - 3659

9
dichlorotetrakis(dimethylsulfoxide)ruthenium(II) [ No CAS ]
sodium cyclopentadienide [ No CAS ]
[ 1287-13-4 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 5151 - 5219

10
chloro-diruthenium(II,III) tetraoctanoate [ No CAS ]
sodium cyclopentadienide [ No CAS ]
[ 1287-13-4 ]

Reference： [1]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1993,vol. 23,p. 589 - 606
[2]Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry,1993,vol. 23,p. 589 - 606

11
decakis(chloromercurio)ruthenocene [ No CAS ]
[ 7732-18-5 ]
[ 1287-13-4 ]

Reference： [1]Organometallics,1997,vol. 16,p. 2498 - 2499

12
[ 10049-08-8 ]
[ 542-92-7 ]
[ 7440-18-8 ]
[ 1287-13-4 ]

Reference： [1]Journal of Organometallic Chemistry,1968,vol. 13,p. 443 - 456
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 199, page 533 - 536
[3]Organic Syntheses,1961,vol. 41,p. 96 - 98
[4]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 199, page 533 - 536

13
[ 10049-08-8 ]
[ 542-92-7 ]
[ 1287-13-4 ]

Reference： [1]Journal of Organometallic Chemistry,1985,vol. 288,p. 341 - 348

14
dichloro-bis-μ-chloro-bis[(1-3η:6-8η)-2,7-dimethyloctadienediyl]diruthenium(II) [ No CAS ]
[ 542-92-7 ]
[ 1287-13-4 ]

Reference： [1]Organometallics,2000,vol. 19,p. 5471 - 5476

15
(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride [ No CAS ]
[ 1287-13-4 ]

Reference： [1]Organometallics,1986,vol. 5,p. 2199 - 2205
[2]Journal of Organometallic Chemistry,1985,vol. 282,p. C49 - C52

16
[ 1287-13-4 ]
[ 33513-42-7 ]
[ 66507-25-3 ]

Reference： [1]Inorganic Chemistry,2021,vol. 60,p. 8227 - 8241
[2]Inorganic Chemistry,2019,vol. 58,p. 2695 - 2707
[3]Inorganica Chimica Acta,2010,vol. 364,p. 132 - 137
[4]Journal of Organometallic Chemistry,1993,vol. 463,p. 163 - 168
[5]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[6]Organometallics,2017,vol. 36,p. 3023 - 3028

17
[ 1287-13-4 ]
[ 33513-42-7 ]
[ 66507-25-3 ]
ruthenocene-1,1'-dicarboxaldehyde [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1993,vol. 463,p. 163 - 168
[2]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[3]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224
[4]Journal of Organometallic Chemistry,1996,vol. 512,p. 219 - 224

18
[ 1287-13-4 ]
[ 29786-93-4 ]
[ 110-18-9 ]
1,1'-dilithioruthenocene*N,N,N',N'-tetramethylethylenediamine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 3321 - 3325

19
[ 1287-13-4 ]
[ 7705-07-9 ]
biruthenocene [ No CAS ]

Reference： [1]Inorganic Chemistry,1992,vol. 31,p. 177 - 182

20
dichloro(1,5-cyclooctadiene)ruthenium(II) [ No CAS ]
[ 3912-86-5 ]
[ 1287-13-4 ]

Reference： [1]Organometallics,1986,vol. 5,p. 2321 - 2327
[2]Journal of Organometallic Chemistry,1985,vol. 288,p. C33 - C36

21
[ 1287-13-4 ]
[ 1079-66-9 ]
[ 114782-43-3 ]

Reference： [1]New Journal of Chemistry,1988,vol. 12,p. 679 - 686
[2]Journal of the Chemical Society, Dalton Transactions,
Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999),1997,p. 1289 - 1294

22
[ 1287-13-4 ]
[ 1293-79-4 ]
ferrocenyl ruthenocenyl ketone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 76 - 82
[2]Canadian Journal of Chemistry,1964,vol. 42,p. 1746 - 1748

23
[ 14284-93-6 ]
[ 1287-13-4 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6146 - 6147
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 172, page 467 - 469

24
[ 1287-13-4 ]
ruthenocene radical cation [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6146 - 6147
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 200, page 536 - 539

25
[ 1287-13-4 ]
ruthenium(IV) [ No CAS ]
ruthenium(III) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 6146 - 6147
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 200, page 536 - 539

26
[ 1287-13-4 ]
biruthenocene [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1990,vol. 399,p. 301 - 306

27
[ 1287-13-4 ]
[ 124-38-9 ]
ruthenocene carboxylic acid [ No CAS ]

Reference： [1]ACS Catalysis,2014,vol. 4,p. 1850 - 1858
[2]Chemistry and industry,
Chemistry and Industry (London, United Kingdom),1958,p. 756 - 757
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 200, page 536 - 539

28
[ 1287-13-4 ]
[ 75-36-5 ]
1-ruthenocenylethan-1-one [ No CAS ]

Reference： [1]Dalton Transactions,2020,vol. 49,p. 1181 - 1190
[2]Inorganic Chemistry,2014,vol. 53,p. 4228 - 4233
[3]Journal of the American Chemical Society,1960,vol. 82,p. 76 - 82

29
[ 1287-13-4 ]
[ 75-36-5 ]
1,1'-diacetylruthenocene [ No CAS ]

Reference： [1]Russian Chemical Bulletin,1997,vol. 46,p. 1458 - 1464
[2]Chemistry and industry,
Chemistry and Industry (London, United Kingdom),1958,p. 756 - 757
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 208, page 554 - 556

30
[ 1287-13-4 ]
[ 93-61-8 ]
trichlorophosphate [ No CAS ]
[ 66507-25-3 ]

Reference： [1]Journal of the American Chemical Society,1962,vol. 84,p. 1845 - 1849

31
(η5-cyclopentadienyl)Ru(CO)2(1-) [ No CAS ]
[ 1835-65-0 ]
[ 1287-13-4 ]
{C₅H₅(CO)2RuC₅F₄N} [ No CAS ]

Reference： [1]Journal of the Chemical Society A: Inorganic, Physical, Theoretical,1968,p. 2158 - 2162

32
(η5-cyclopentadienyl)Ru(CO)2(1-) [ No CAS ]
[ 1835-65-0 ]
[ 1287-13-4 ]
{C₅H₅(CO)2Ru(C₆F₃(CN)2)} [ No CAS ]

Reference： [1]Journal of the Chemical Society A: Inorganic, Physical, Theoretical,1968,p. 2158 - 2162

33
[ 1287-13-4 ]
[ 98-88-4 ]
1,1'-dibenzoylruthenocene [ No CAS ]
benzoylruthenocene [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1986,vol. 64,p. 1943 - 1948
[2]Chemistry and industry,
Chemistry and Industry (London, United Kingdom),1958,p. 756 - 757
[3]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Ru: SVol., 208, page 554 - 556

34
[ 1287-13-4 ]
[ 98-88-4 ]
benzoylruthenocene [ No CAS ]

Reference： [1]Chemistry and industry,
Chemistry and Industry (London, United Kingdom),1958,p. 756 - 757

35
[ 1287-13-4 ]
[ 103-71-9 ]
(C₅H₅)Ru(C₅H₄(CONHC₆H₅)) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 76 - 82

36
ammonium hexafluorophosphate [ No CAS ]
[ 1287-13-4 ]
{ruthenoceniumBr}PF₆ [ No CAS ]

Reference： [1]Inorganic Chemistry,1984,vol. 23,p. 1943 - 1945

37
ammonium hexafluorophosphate [ No CAS ]
[ 1287-13-4 ]
{ruthenoceniumCl}PF₆ [ No CAS ]

Reference： [1]Inorganic Chemistry,1984,vol. 23,p. 1943 - 1945

38
pentakis(acetoxymercurio)pentamethylruthenocene [ No CAS ]
[ 917-54-4 ]
[ 1287-13-4 ]
[ 100462-22-4 ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 6468 - 6469

39
[ 1287-13-4 ]
[ 1600-27-7 ]
deca(acetoxymercurio)ruthenocene [ No CAS ]

Reference： [1]Angewandte Chemie,1993,vol. 105,p. 1247 - 1249
[2]Organometallics,1994,vol. 13,p. 3009 - 3019

40
[ 1287-13-4 ]
[ 124-73-2 ]
[ 101178-14-7 ]

Reference： [1]Chemistry Letters,1985,p. 1063 - 1066
[2]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 3540 - 3546

41
[ 1287-13-4 ]
ruthenocene carboxylic acid [ No CAS ]
[ 147041-84-7 ]

Reference： [1]Organometallics,1996,vol. 15,p. 4888 - 4890

42
[ 1287-13-4 ]
[ 75-09-2 ]
ethoxymethyl ruthenocene [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3263 - 3265
[2]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3263 - 3265

43
ruthenium trichloride hydrate [ No CAS ]
[ 4249-10-9 ]
[ 542-92-7 ]
[ 1287-13-4 ]
[ 123283-74-9 ]
[ 264910-31-8 ]

Reference： [1]Inorganic Chemistry,2000,vol. 39,p. 1573 - 1577

44
[ 1287-13-4 ]
[ 1191-47-5 ]
[ 3525-44-8 ]
[ 17589-14-9 ]
[ 108-18-9 ]
[Ru(C₅H₃)2]Na₄Mg₄(diisopropylamide)8] [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 11612 - 11620

45
[ 1287-13-4 ]
[ 814-68-6 ]
[ 667456-06-6 ]

Reference： [1]Journal of Organometallic Chemistry,2004,vol. 689,p. 252 - 263

46
[ 1287-13-4 ]
[ 109-63-7 ]
biruthenocenium tetrafluoroborate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1999,vol. 72,p. 715 - 723

47
[ 1287-13-4 ]
[ 36982-84-0 ]
[ 603-35-0 ]
[ 960209-73-8 ]

Reference： [1]Organometallics,2007,vol. 26,p. 6234 - 6242

48
[ 3437-95-4 ]
[ 473926-52-2 ]
[ 1287-13-4 ]
[ 1007403-60-2 ]

Reference： [1]Journal of Organometallic Chemistry,2008,vol. 693,p. 247 - 256

49
[ 1287-13-4 ]
[ 74-96-4 ]
[ 32992-96-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a nitrogen-replaced flask, 5.0 mL of a hexane solution containing n-butyllithium (concentration: 2.6 mol/L) was placed and cooled to -78 C. After 1.74 g of bis(cyclopentadienyl)ruthenium was added, 50 mL of tetrahydrofuran was added dropwise over one hour to react them. The reaction solution was allowed to stand for 2 hours to return the temperature to room temperature and thereafter a reaction was performed for 24 hours. The reaction solution was again cooled to -78 C., 9.81 g of ethyl bromide was added dropwise over one hour to react them, allowed to stand for 2 hours to room temperature, and the reaction was performed for 24 hours. After completion of the reaction, 100 mL of water was added and bis(ethylcyclopentadienyl)ruthenium was extracted with hexane and then hexane was evaporated from the extraction solvent to obtain 2.0 g of bis(ethylcyclopentadienyl) ruthenium.

Reference： [1]Patent: US7002032,2006,B2 .Location in patent: Page/Page column 6-7

50
[ 109-04-6 ]
[ 1287-13-4 ]
[ 7646-85-7 ]
[ 1304099-24-8 ]

Reference： [1]Inorganica Chimica Acta,2011,vol. 370,p. 224 - 229

51
tetrafluoroboric acid [ No CAS ]
[ 1287-13-4 ]
[ 91-20-3 ]
[ 100506-76-1 ]

Yield	Reaction Conditions	Operation in experiment
60%		Under inert atmosphere, an oven-dried two neck round-bottom flask (500 ml.) equipped with a reflux condenser and a Teflon-coated egg-shaped magnetic stirring bar was charged with <strong>[1287-13-4]ruthenocene</strong> (S1) (4.52 g, 19.5 mmol, 1.00 equiv), naphthalene (25.0 g, 195 mmol, 10.0 equiv), AICI3 (2.61 g, 19.5 mmol, 1.00 equiv), and aluminum powder (-325 mesh, 99.7%, 264 mg, 9.77 mmol, 0.500 equiv). Then dry decalin (0.13 L, c = 0.15 M) was added, followed by dropwise addition of TiCI4 (1.07 ml_, 1.85 g, 9.77 mmol, 0.500 equiv) via a syringe. The resulting red suspension was heated to 140 C and was then stirred for 50 hours at 140 C. The oil bath was removed, and after cooling to room temperature, the reaction mixture was poured onto a mixture of ice (150 g), aqueous concentrated HCI-solution (28 ml_), and H202 (35% solution in H20, 28 ml_). The aqueous layer was separated from the organic layer with the aid of a separatory funnel, and the aqueous layer was washed with pentane (2 x 100 ml_). The combined organic layers were extracted with water (50 ml_), and then fluoroboric acid (48% solution in water, 5.1 ml_, 7.2 g, 39 mmol, 2.0 equiv) was added to the combined aqueous layers in the reaction flask. The resulting orange solution was stirred for 15 minutes, and then the suspension was extracted with dichloromethane (4 x 100 ml_). The combined organic layers were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to dryness. The brown residue was dissolved in dichloromethane (15 ml.) and then added dropwise through a syringe-filter to vigorously stirred diethyl ether (150 ml_). The suspension was filtered through a 60 ml. Buchner funnel with micro porosity (code M), and the pale yellow solid was washed with diethyl ether (2 x 30 ml_), and dried in vacuo to afford 2 as a yellow solid (4.50 g, 11.8 mmol, 60% yield). (0099) HRMS-EI (m/z) calc’d for CI5H13RU [M-BF4]+, 295.00553; found, 295.00563; deviation: 0.35 ppm.

Reference： [1]European Journal of Inorganic Chemistry,2012,p. 1485 - 1492
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 14207 - 14211
Angew. Chem.,2018,vol. 130,p. 14403 - 14407
[3]Patent: WO2020/7893,2020,A1 .Location in patent: Page/Page column 14

52
[ 1287-13-4 ]
[ 3030-47-5 ]
1,1'-dilithioruthenocene - N,N,N',N',N''-pentamethyldiethylenetriamine (1/1) [ No CAS ]

Reference： [1]Organometallics,2012,vol. 31,p. 6317 - 6321

53
[ 1287-13-4 ]
[ 7553-56-2 ]
[ 70210-62-7 ]

Yield	Reaction Conditions	Operation in experiment
59%		RcH (624mg, 2.7 mmol)was dissolved in freshly distilled THF (40 mL). 1.0 M THFsolution of KOtBu (0.34mL, 0.34mmol) was added into thereaction mixture. Then, the mixture was cooled at 80 C andstirred for 15 min. 1.2M pentane solution of LitBu (4.5mL,5.4 mmol) was added dropwise. The concentration of LitBusolution was determined by a reported titration method beforeuse.26 The mixture was stirred at 80C. After 2h, ground I2(1.03 g, 4.1mmol) was added, and the stirring was continuedfor another 22 h at that temperature. Then, the reaction wasquenched with 5mL of EtOH at 80 C, and warmed to roomtemperature. The mixture was washed with saturated Na2S2O3aqueous solution to deactivate excess I2. CH2Cl2 was added,and the organic layer was separated and dried over MgSO4.After evaporation of solvent, the residue was purified by flashcolumn chromatography using alumina as the stationary phaseand hexane as eluent. RcI was obtained as white-yellow solid(566mg, 59% yield). Anal. Calcd for C10H9IRu: C, 33.63; H,2.54%. Found for RcI: C, 33.64; H, 2.41%. 1HNMR(CDCl3): 4.46 (t, 2H, (C5H5)Ru(CH2CH2CI)), 4.57 (s, 5H, (C5H5)Ru-(C4H4I)), 4.83 (t, 2H, (C5H5)Ru(CH2CH2CI))ppm.

Reference： [1]Bulletin of the Chemical Society of Japan,2016,vol. 89,p. 1344 - 1353
[2]Organometallics,2013,vol. 32,p. 2037 - 2040

54
[ 1287-13-4 ]
[ 579-10-2 ]
[ 66507-25-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The compounds Cc+COOH·PF6- (7) [28,29], FcCOOH (4) [59], RcCOOH (5) [60], OcCOOH (6) [61], FcCHO (1) [59] and RcCHO (2) [62] were synthesized as described before. Details on the synthesis of OcCHO is non-existent although a report exists where the authors mentioned it was synthesized in an analogous way to RcCHO via monolithiation and addition of DMF [63]. We used the following procedure (Scheme 1): a solution of N-methylformanilide (14ml) and POCl3 (7.5ml) was stirred for 1h at room temperature under an argon atmosphere before osmocene (700mg, 2.2mmol) dissolved in toluene (10ml) was added drop wise. The mixture was heated up to 80C and kept at this temperature for 2h. After cooling to 0C, CH3COONa (5g, 61mmol) dissolved in water (100ml) was slowly added and subsequently the mixture was stirred for 24h at room temperature. The organic layer was washed with 1M HCl, water, saturated solution of Na2CO3 and again water, dried and evaporated. Finally, the crude aldehyde was cleaned by column chromatography with n-hexane:diethyl ether combination in 3:4 ratio, Rf=0.5. Yellow, parallel-piped crystals suitable for X-ray diffraction were grown from acetone in 79% yield (275mg). 1H NMR δH (300MHz, CDCl3)/ppm: 4.86 (5H, s, C5H5), 5.02 (2H, t, C5H4), 5.22 (2H, t, C5H4). Calculated for C11H10OOs: C, 37.92; H, 2.89; O, 4.59; Os, 54.60%. Found: C, 37.90; H, 2.90; O, 4.75%.

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 745-746,p. 393 - 403

55
[ 1287-13-4 ]
[ 1079-66-9 ]
[ 1356191-89-3 ]

Yield	Reaction Conditions	Operation in experiment
19%		Ruthenocene (1g, 4.3mmol) was dissolved in dry THF (15ml) and the system degassed under Ar for 30min. The solution was cooled to-78C and t-butyl lithium (2.55ml, 4.3mmol, 1eq. Warning: t-butyl lithium combusts spontaneously upon air exposure) was added dropwise to the solution under Ar. The solution was allowed to warm to room temperature and stirred for 2h. It was again cooled to-78C and chlorodiphenylphosphine (2.34ml, 13.0mmol, 3eq.) was slowly added under Ar. The solution was allowed to warm to room temperature and stirred for a further 2 days. The reaction mixture was quenched with saturated sodium bicarbonate and extracted with CH2Cl2. The product was separated by column chromatography, (Rf=0.81) to yield 0.34g (19%) of 2, m.p.=127C. Recrystallisation of 2 from CH2Cl2 and n-hexane gave crystallographic quality crystals. Elemental analysis (%): calc. for C22H19RuP (415.4): C, 63.6; H, 4.6; found: C, 63.5; H, 4.6. 1H NMR (CDCl3, δ, ppm): 4.47 (s, 5H, C5H5); 4.50 (t, 2H, 0.5× C5H4, 3JHH 1.61Hz), 4.73 (t, 2H, 0.5× C5H4, 3JHH 1.65Hz); 7.36 (m, 10H, 2× C6H5). 31P{1H} NMR (CDCl3, δ, ppm):-16 (s, P). 13C{1H} NMR (CDCl3, δ, ppm): 72 (s, C5H5); 73 (d, C5H4, 3JPC 3Hz); 75 (d, C5H4, 2JPC 16Hz); 80 (d, Cq/C5H4, 1JPC 9Hz); 128 (d, C6H5, 3JPC 7Hz); 128 (s, C6H5); 133 (d, C6H5, 2JPC 19Hz); 139 (d, Cq/C6H5, 1JPC 10Hz).

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 754,p. 80 - 87

56
[ 1287-13-4 ]
[ 70210-63-8 ]
[ 70210-62-7 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 3662 - 3667

57
[ 1287-13-4 ]
[ 540-72-7 ]
[ 1584163-40-5 ]
[ 183667-33-6 ]
[ 1584163-41-6 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 3662 - 3667

58
[ 1287-13-4 ]
[ 16420-13-6 ]
C₁₆H₂₀N₂RuS₂ [ No CAS ]

Reference： [1]ACS Catalysis,2014,vol. 4,p. 1850 - 1858

59
[ 1287-13-4 ]
[ 132524-91-5 ]
tert-butyl (E)-4-ruthenocenylbut-2-enoate [ No CAS ]

Reference： [1]Organometallics,2014,vol. 33,p. 5924 - 5927

60
[ 1287-13-4 ]
[ 1490-25-1 ]
4-oxo-4-ruthenocenyl butyric methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With aluminum (III) chloride; In dichloromethane; for 12h;	A1C13 (0.8 g, 6 mmol) was added slowly to the solution of <strong>[1287-13-4]ruthenocene</strong> (1.3 g, 6 mmol) in 15 ml of DCM. 0.34 ml methyl 4-chloro-4-oxobutanoate (6 mmol) was added dropwise to the first solution and the resulting mixture was stirred for 12 firs. Then the reaction was quenched by water. The aqueous layer was extracted three times with dichloromethane. The organic layer was dried over MgS04 and evaporated. The residue was purified by column chromatography on silica gel eluting with PE:EtOAc (6: 1) to give methyl 4-oxo-4-ruthenocenyl butanoate as a light yellow solid 0.9 g, yield 43%. 1H NMR (300 MHz, CDC13): δ 2.64 (t, J= 6.7 Hz, 2H, CH2), 2.98 (t, J= 6.7 Hz, 2H, CH2), 3.70 (s, 3H, OCH3), 4.62 (s, 5H, C5H5), 4.78 (t, J= 3.0 Hz, 2H, C5H4), 5.13 (t, J= 3.0 Hz, 2H, C5H4).
43%	With aluminum (III) chloride; In dichloromethane; for 12h;	(prepared according to M. Aslam Siddiqi et al.Materials 2010, 3, 1172-1185) AlCl3 (0.8 g, 6 mmol) was added slowly to the solution of <strong>[1287-13-4]ruthenocene</strong> (1.3 g, 6 mmol) in15 ml of DCM. 0.34 ml methyl 4-chloro-4-oxobutanoate (6 mmol) was added dropwise to the first solution and the resultingmixture was stirred for 12 hrs. Then the reaction was quenched by water. The aqueous layer was extracted three timeswith dichloromethane. The organic layer was dried over MgSO4 and evaporated. The residue was purified by columnchromatography on silica gel eluting with PE:EtOAc (6:1) to give methyl 4-oxo-4-ruthenocenyl butanoate as a light yellowsolid 0.9 g, yield 43%. 1H NMR (300 MHz, CDCl3): δ 2.64 (t, J= 6.7 Hz, 2H, CH2), 2.98 (t, J= 6.7 Hz, 2H, CH2), 3.70 (s,3H, OCH3), 4.62 (s, 5H, C5H5), 4.78 (t, J= 3.0 Hz, 2H, C5H4), 5.13 (t, J= 3.0 Hz, 2H, C5H4)

Reference： [1]Patent: WO2015/63201,2015,A1 .Location in patent: Page/Page column 25
[2]Patent: EP2868664,2015,A1 .Location in patent: Paragraph 0121

61
[ 1287-13-4 ]
[ 133745-75-2 ]
monofluororuthenocene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: Under a positive pressure of argon, the respective metallocene(1 equiv.) and potassium tert-butoxide (0.125 equivalents) weredissolved in dry tetrahydrofuran (1 mmol in 10 ml). The solution ofthe metallocene was cooled to 78 C and the solution of tertbutyllithiumin n-heptane (1.6 M, 2 equivs.) was added slowly,ensuring that the temperature did not exceed 70 C. Stirring wascontinued for 60 min at 78 C. After that, the suspension wastransferred into a solution of NFSI (2.5 equivs.) in dry diethylether(7 ml per 1 mmol) at 20 C. Then, the reaction mixture wasdirectly subjected to a water-cooled column containing neutralalumina gel (activity III, diameter 2 cm, length 25 cm). The columnwas eluted with hexanes until the eluent was colorless (for 1) or approx. four times (for 6), in order to remove excess NFSI and otherpolar byproducts. The solvent was removed in vacuo.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 797,p. 125 - 130

62
[ 67969-82-8 ]
[ 1287-13-4 ]
[ 75-05-8 ]
[ 107799-44-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	at 0 - 20℃; for 20h;Inert atmosphere;	Example 1 In an argon atmosphere, 2.35 g (14.5 mmol) of a tetrafluoroboric acid-diethyl ether complex was added at 0C to a suspension prepared by mixing 3.15 g (13.6 mmol) of bis(η5-cyclopentadienyl)ruthenium ((η5-C5H5)2Ru) and 30 mL of acetonitrile. The resulting mixture was stirred at room temperature for 20 hours, and the solvent was then removed by distillation under reduced pressure. The remaining solid was washed with a mixture of dichloromethane and diethyl ether (dichloromethane:diethyl ether=1:13 (vol%)) to obtain [tris(acetonitrile)(η5-cyclopentadienyl)ruthenium(II)][tetrafluoroborate] ([Ru(η5-C5H5)(MeCN)3][BF4]) as a yellow solid (4.30 g, yield: 84%). 1H-NMR (500 MHz, CDCl3, δ): 4.21 (s, 5H), 2.43 (s, 9H). 13C-NMR (125 MHz, CDCl3, δ): 125.5,68.8,4.05.

Reference： [1]Patent: EP2930179,2015,A1 .Location in patent: Paragraph 0167; 0168

63
[ 1287-13-4 ]
[ 28995-88-2 ]
ruthenocenylethynylbenzene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 15645 - 15649

64
[ 1287-13-4 ]
[ 4659-45-4 ]
2,6-dichlorobenzoylruthenocene [ No CAS ]