[ CAS No. 37366-09-9 ] {[proInfo.proName]}

Name: 37366-09-9|Dichloro(benzene)ruthenium(II) dimer|97%
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Quality Control of [ 37366-09-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 37366-09-9 ]

Product Details of [ 37366-09-9 ]

CAS No. :	37366-09-9	MDL No. :	MFCD00064686
Formula :	C₁₂H₁₂Cl₄Ru₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YGXMUPKIEHNBNQ-UHFFFAOYSA-J
M.W :	500.18	Pubchem ID :	10962144
Synonyms :	Benzeneruthenium(II) chloride dimer

Calculated chemistry of [ 37366-09-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	76.3
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	7.26
Log Po/w (WLOGP) :	-8.61
Log Po/w (MLOGP) :	4.92
Log Po/w (SILICOS-IT) :	2.12
Consensus Log Po/w :	1.14

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-8.01
Solubility :	0.00000491 mg/ml ; 0.0000000098 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.08
Solubility :	0.0000411 mg/ml ; 0.0000000822 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-2.27
Solubility :	2.67 mg/ml ; 0.00535 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.0

Safety of [ 37366-09-9 ]

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 [ 37366-09-9 ]

* 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 [ 37366-09-9 ]
Downstream synthetic route of [ 37366-09-9 ]

[ 37366-09-9 ] Synthesis Path-Upstream 1~20

1
[ 1165952-91-9 ]
[ 37366-09-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 45℃; for 3 h;	Synthesis of theruthenium dimer: [Ru(η⁶-C₆H₆)Cl₂]₂This complex wassynthesized by following the published procedure.[1] 1.7g (3,5.10^-3mol) of RuCl₃.3H₂O and 6mL of 1,3-cyclohexadiene (6,3.10^-2mol)were dissolved in 100 mL of a90percent aqueous ethanol solution. The red solution was stirred for 3h at 45°C. Thisresulting red precipitate was collected, washed with ethanol, and dried invacuum. Yield: 85percent.[1] R. A.Zelonka, M. C. Baird, Canadian Journal Chem, 1972, 50, 3063.

Reference： [1] Journal of Organometallic Chemistry, 2014, vol. 760, p. 248 - 259
[2] MedChemComm, 2014, vol. 5, # 5, p. 597 - 602

2
[ 1165952-92-0 ]
[ 37366-09-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	at 80 - 85℃; for 12 h;	According to the synthesis of the references (Inorg. Synth., (1982, 21, 74)A mixture of 2 OOg RuCl3.3H20 (9.64 mmol)And 10. 0 mL of 1,4-cyclohexanediol (106 mmol) were dissolved in 100 mL of ethanol at a temperature of 80 to 85 ° C and heated to reflux for 12 h. After cooling, the resulting brown mixture was suction filtered to give a brown powder which was washed with a small amount of methanol and dried in vacuo to give 1.96 g of a brown solid, yield: 81percent

Reference： [1] Patent: CN103509059, 2016, B, . Location in patent: Paragraph 0043; 0045; 0051-0053
[2] Chemistry - A European Journal, 2018,

3
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Reference： [1] Green Chemistry, 2016, vol. 18, # 6, p. 1469 - 1474
[2] Tetrahedron, 2013, vol. 69, # 39, p. 8360 - 8367
[3] Inorganic Chemistry, 2018, vol. 57, # 21, p. 13552 - 13563

4
[ 99-85-4 ]
[ 37366-09-9 ]

Reference： [1] Patent: CN108794542, 2018, A, . Location in patent: Paragraph 0032; 0033; 0034
[2] Patent: CN108794543, 2018, A, . Location in patent: Paragraph 0033; 0034

5
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Reference： [1] Inorganic Chemistry, 2011, vol. 50, # 19, p. 9714 - 9727
[2] Journal of Organometallic Chemistry, 1981, vol. 208, # 3, p. 369 - 387

6
[ 68193-73-7 ]
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Reference： [1] Journal of Organometallic Chemistry, 1984, vol. 263, # 3, p. 375 - 384

7
[ 10049-08-8 ]
[ 1165952-91-9 ]
[ 37366-09-9 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, p. 1922 - 1926[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, p. 2071 - 2076
[3] Russian Chemical Bulletin, 2005, vol. 54, # 10, p. 2374 - 2378

8
[ 2886-59-1 ]
[ 107-21-1 ]
[ 37366-09-9 ]
[ 659738-59-7 ]

Reference： [1] Organometallics, 2005, vol. 24, # 10, p. 2538 - 2541

9
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[ 37366-09-9 ]

Reference： [1] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1991, # 10, p. 2693 - 2702

10
[ 143-66-8 ]
[ 37366-09-9 ]

Reference： [1] Journal of Organometallic Chemistry, 1984, vol. 264, # 3, p. 365 - 378

11
[ 20759-14-2 ]
[ 1165952-92-0 ]
[ 37366-09-9 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2002, # 3, p. 416 - 427

12
[ 64-17-5 ]
[ 2886-59-1 ]
[ 37366-09-9 ]

Reference： [1] Organometallics, 2005, vol. 24, # 10, p. 2538 - 2541

13
[ 54913-13-2 ]
[ 37366-09-9 ]

Reference： [1] Journal of Organometallic Chemistry, 1988, vol. 354, p. 117 - 122

14
[ 71-43-2 ]
[ 37366-09-9 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 33, p. 11568 - 11573

15
[ 1165952-91-9 ]
[ 37366-09-9 ]

Reference： [1] Organometallics, 2000, vol. 19, # 5, p. 790 - 797

16
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[ 37366-09-9 ]

Reference： [1] Journal of Organometallic Chemistry, 1981, vol. 208, # 3, p. 369 - 387

17
[ 71-43-2 ]
[ 37366-09-9 ]

Reference： [1] Journal of Organometallic Chemistry, 2012, vol. 714, p. 88 - 93

18
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[ 37366-09-9 ]

Reference： [1] Chemical Communications, 2016, vol. 52, # 71, p. 10735 - 10738

19
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[ 37366-09-9 ]

Reference： [1] Tetrahedron Asymmetry, 2017, vol. 28, # 12, p. 1739 - 1749

20
[ 2886-59-1 ]
[ 37366-09-9 ]
[ 52462-30-3 ]

Reference： [1] Organometallics, 2018, vol. 37, # 7, p. 1092 - 1102

[ 37366-09-9 ] Synthesis Path-Downstream 1~87

1
[ 20759-14-2 ]
[ 1165952-92-0 ]
[ 37366-09-9 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 416 - 427

2
[ 37366-09-9 ]
[ 240417-00-9 ]
Me₂NC₆H₄C₆H₄PPh₂Ru(C₆H₆)Cl₂ [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1482 - 1483

3
[ 37366-09-9 ]
[ 461-89-2 ]
[ 135252-87-8 ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 410,p. 73 - 84

4
[ 37366-09-9 ]
[ 461-89-2 ]
{(η6-C6H6)Ru(μ-OH)2(μ-C3N3O2H2)Ru(η6-C6H6)}Cl [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1991,vol. 410,p. 73 - 84

5
[ 37366-09-9 ]
[ 443-72-1 ]
{(η6-benzene)RuCl(μ-N6-methyladeninate)}4 [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1993,vol. 206,p. 15 - 22

6
[ 37366-09-9 ]
[ 247940-06-3 ]
[ 568592-69-8 ]

Reference： [1]Organometallics,2003,vol. 22,p. 2749 - 2757

7
[ 37366-09-9 ]
[ 22795-99-9 ]
[Ru(II)((S)-(-)-2-aminomethyl-1-ethylpyrrolidine)(η6-benzene)Cl]Cl [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2004,vol. 357,p. 1247 - 1255

8
[ 37366-09-9 ]
[ 25372-03-6 ]
[ 832103-23-8 ]

Reference： [1]Inorganic Chemistry,2004,vol. 43,p. 8600 - 8608

9
[ 37366-09-9 ]
sodium hexafluoroantimonate [ No CAS ]
[ 148461-14-7 ]
[chloro((4S)-2-(2-diphenylphosphanylphenyl)-4-isopropyl-1,3-oxazoline)(benzene)ruthenium(II)] hexafluoroantimonate [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2006,p. 3155 - 3166

10
[ 37366-09-9 ]
[ 251320-86-2 ]
[ 568592-70-1 ]

Reference： [1]Organometallics,2003,vol. 22,p. 2749 - 2757

11
[ 37366-09-9 ]
[ 2820-37-3 ]
[C₆H₆RuCl₂((CH₃)2C₃H₂N₂)] [ No CAS ]

Reference： [1]Polyhedron,2004,vol. 23,p. 885 - 894

12
[ 37366-09-9 ]
[ 99646-28-3 ]
[((R)-tol-BINAP)RuCl₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 100℃; for 0.166667h;	A 200-mL Schlenk tube was charged with [RuCl2(benzene)]2 (2.0 g, 4.0 mmol) and <strong>[99646-28-3](R)-tol-BINAP</strong> (5.7 g, 8.4 mmol). The tube was put under vacuum for 15 minutes and then back flushed with argon. DMF (133 mL, degassed with argon) was added to the tube and the mixture was flushed with argon. The tube was closed and heated to 100 C. for 10 minutes (stirring). The DMF was then removed under high vacuum at 70 C. to give [(<strong>[99646-28-3](R)-tol-BINAP</strong>)RuCl2(DMF)x] as a reddish/brown solid (See, Org. Syn. 71, 1993, 1-13).

Reference： [1]Patent: US2008/318973,2008,A1 .Location in patent: Page/Page column 46

13
[ 37366-09-9 ]
[ 35132-20-8 ]
[ 99646-28-3 ]
trans-RuH(η1-BH4)[(R)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl][(R,R)-1,2-diphenylethylenediamine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		trans-RuH(eta1-BH4)[(R)-tolbinap][(R,R)-dpen] was synthesized. First, trans-RuCl2[(R)-tolbinap][(R,R)-dpen] was synthesized. That is, [RuCl2(benzene)]2 (129 mg; 0.258 mmol) (made by Aldrich Inc.) and (R)-TolBINAP (373 mg; 0.55 mmol) (made by AZmax Co., Ltd.) were weighed and placed in a 50 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding DMF (9 mL) with a syringe, heating in an oil bath set to 100 C. was performed for 10 minutes under an argon atmosphere. After cooling the reaction solution to room temperature, (R, R)-DPEN (117 mg; 0.55 mmol) (made by Kankyo Kagaku Center Co., Ltd.) was added under an argon gas flow to the reddish-brown RuCl2[(R)-tolbinap](dmf)n solution, and stirring at 25 C. was performed for 3 hours. To a green-colored crude product obtained by distilling off the DMF under reduced pressure (1 mmHg), methylene chloride (10 mL) was added, and after dissolving as much of a yellow product as possible, a green impurity was removed by filtration. The yellow solution that was obtained by filtration whereafter concentrated to approximately 1 mL and then diethyl ether (5 mL) was added to precipitate solids. The solids obtained were separated by filtration and dried under reduced pressure(1 mmHg)to obtain trans-RuCl2[(R)-tolbinap][(R,R)-dpen] (340 mg; 0.32 mmol; yield: 58%) as a yellow powder. [TolBINAP] and [tolbinap] are abbreviations for 2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl, ?DMF? and ?dmf? are abbreviations for N,N-dimethylformamide, and ?DPEN? and ?dpen? are abbreviations for 1,2-diphenylethylenediamine. [00030] The abovementioned trans-RuCl2[(R)-tolbinap] [(R,R)-dpen] (106.3 mg; 0.1 mmol) and sodium borohydride (94.6 mg; 2.5 mmol) (made by Nacalai Tesque, Inc.) were then weighed and placed in a 50 mL Schlenk reaction tube equipped with a stirrer coated with polytetrafluoroethylene, and after depressurizing the interior of the vessel to eliminate air, argon was introduced. After then adding a 1:1 volume ratio mixed solvent of benzene/ethanol (4 mL) with a syringe, heating in an oil bath set to 65 C. was performed for 5 minutes under an argon atmosphere. The reaction solution was thereafter stirred for 30 minutes at room temperature. After then drying and solidifying the crude product by distilling off the solvent under reduced pressure (1 mmHg), benzene (6 mL) was added under an argon gas flow to dissolve as much of a yellow product as possible and then the excess sodium borohydride was eliminated by filtration by celite (0.5 g). A yellow filtrate thus obtained was concentrated to approximately 1 ml by depressurization (1 mm Hg) and hexane (6 mL) was then added under an argon gas flow. Yellow solids thus precipitated were separated by filtration through a glass filter and dried under reduced pressure (1 mmHg) to obtain trans-RuH(eta1-BH4)[(R)-tolbinap] [(R,R)-dpen] (76.0 mg; yield: 70%; see formula (3) below) as a yellow powder. Decomposition temperature: 164 C.; 1HNMR(400 MHZ, C6D6) delta-13.60(t, 1, J=22.4 Hz, RuH), -0.40(brs, 4, BH4), 1.45(s, 3, CH3), 1.55(s, 3, CH3), 1.62(s, 3, CH3), 1.63(s, 3, CH3), 1.95(dd, 1, J=7.2 and 8.4 Hz, NHH), 2.38(d, 1, J=8.2 Hz, NHH) ,3.65(dd, 1, J=7.9 and 11.2 Hz, CHNH2), 3.82-3.88(m, 2, 2 NHH), 4.00(ddd, 1, J=7.9, 8.4 and 11.6 Hz, CHNH2), 6.13-8.12(m, 38, aromatics) ;31PNMR(161.7 MHz, C6D6) delta71.2(d, J=41.4 Hz), 75.2(d, J=41.4 Hz);IR(toluene)2316(s), 1862(s), 1092(s), 1080(s)cm-1; ESI-MS m/z1007.26([M-H]+), theoretical value (C62H60BN2P2Ru): 1007.34. The powder obtained was then recrystallized from a THF/hexane mixed solvent of a volume ratio of approximately 1:5 to obtain yellow prismatic crystals, and these were used for X-ray crystallography.

Reference： [1]Patent: US6720439,2004,B1 .Location in patent: Page/Page column 7-8

14
[ 37366-09-9 ]
[ 54-05-7 ]
[ 1108749-82-1 ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 1122 - 1131

16
[ 3731-51-9 ]
[ 37366-09-9 ]
[ 99646-28-3 ]
[dichloro((R)-2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl)(α-picolylamino)ruthenium(II)] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		A ruthenium complex (R)-1 (RuCl2[(R)-tolbinap](pica)) shown in chemical formula 2 below was synthesized as follows. First, 105.5 mg (0.21 mmol) [RuCl2(eta6-benzene)]2 (Aldrich Chemical), 2 equivalents (R)-TolBINAP (286.0 mg, 0.42 mmol) (AZmax Co.), and 5.0 mL DMF were placed in a 10 mL Schlenk flask under argon atmosphere to prepare a solution. After argon was passed through the solution for five minutes, the solution was heated at 100C for 10 minutes. The solvent was then removed under vacuum, 45.4 mg (0.42 mmol) of 2-picolylamine (PICA) (Tokyo Chemical Industry Co., Ltd.) was added thereto along with 3.0 mL of methylene chloride, and the resulting solution was stirred for 2 hours. By decreasing the volume to about 0.5 mL and then adding hexane (2 mL), yellow precipitates were formed. The supernatant was removed by filtration, and the resulting powder was vacuum-dried to yield a ruthenium complex (R)-1 in 86% yield (322.0 mg). The ruthenium complex (R)-1 was used in the hydrogenation reaction described below without purification. The melting point was >150C (decomposition point). The ruthenium complex (R)-1 was obtained as a diastereomer mixture. By heating this mixture at 80C for 30 minutes in toluene, the content of the main diastereomer increased to >90% in terms of relative integral. The spectrum data of the ruthenium complex (R)-1 was as follows: 1HNMR (400 MHz, C6D6) delta1.78(s, 3, CH3), 1.90(s, 3, CH3), 2.28(s, 3, CH3), 2.33(s, 3, CH3), 2.86(br s, 1, NHH), 3.22(br s, 1, NHH), 3.95(br s, 1, CHH), 4.93(br s, 1, CHH), 6.19-8.36(m, 32, aromatics); 31PNMR(161.7 MHz, C6D6) delta44.74(d, J = 35.6 Hz), 41.93 (d, J = 35.6 Hz). However, the reaction rate and the enantioselectivity of the hydrogenation reaction of the ketone described below are independent of the initial diastereomer mixture.

Reference： [1]Patent: EP1813621,2007,A1 .Location in patent: Page/Page column 4

17
[ 17084-13-8 ]
[ 37366-09-9 ]
[ 75-05-8 ]
[ 391604-55-0 ]
[ 1301766-98-2 ]

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 13579 - 13592
[2]European Journal of Inorganic Chemistry,2011,p. 1806 - 1814
[3]Journal of Organometallic Chemistry,2012,vol. 714,p. 88 - 93

18
[ 37366-09-9 ]
[ 142646-58-0 ]
[ 1332307-95-5 ]

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

19
[ 17084-13-8 ]
[ 37366-09-9 ]
[ 387827-64-7 ]
[ 75-05-8 ]
[ 1392046-22-8 ]

Reference： [1]Journal of Organometallic Chemistry,2012,vol. 714,p. 88 - 93

20
[ 37366-09-9 ]
[ 17985-72-7 ]
[ 1428536-29-1 ]

Reference： [1]Organometallics,2013,vol. 32,p. 2112 - 2120

21
[ 37366-09-9 ]
[ 18741-85-0 ]
[ 99646-28-3 ]
((R)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl)-RuCl₂-((R)-(+)-1-1'-bi(2-naphtylamine)) [ No CAS ]

Reference： [1]Catalysis Today,2013,vol. 213,p. 109 - 114

22
[ 37366-09-9 ]
[ 99646-28-3 ]
[ 3685-05-0 ]
[ 1448454-21-4 ]

Reference： [1]Catalysis Today,2013,vol. 213,p. 109 - 114

23
[ 37366-09-9 ]
[ 1190077-27-0 ]
[ 7650-91-1 ]
RuCl2{P(BnPh2)3}2{(1S,1’S)-1,1’-biisoindoline} [ No CAS ]

Reference： [1]ChemCatChem,2013,vol. 5,p. 2253 - 2257

24
[ 4318-37-0 ]
[ 37366-09-9 ]
ammonium hexafluorophosphate [ No CAS ]
[Ru(η6-benzene)(N-methylhomopiperazine)Cl](PF6) [ No CAS ]