14647-23-5

Basic information

• Product Name: 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride
• Synonyms: DICHLORO[1,2-BIS(DIPHENYLPHOSPHINO)ETHANE]NICKEL(II);DICHLORO[BIS(1,2-DIPHENYLPHOSPHINO)ETHANE]NICKEL(II);1,2-BIS(DIPHENYLPHOSPHINE)ETHANE NICKEL(II) CHLORIDE;[1,2-BIS(DIPHENYLPHOSPHINO)ETHANE]DICHLORONICKEL(II);1,2-BIS(DIPHENYLPHOSPHINO)ETHANE NICKEL(II) CHLORIDE;[1,2-BIS(DIPHENYLPHOSPHINO)ETHANE]NICKEL(II) DICHLORIDE;1,2-Bis(diphenylphosphinoethane)nickel(II) chloride[Ni(dppe)Cl2];1,2-Bis-(Diphenylphosphino)EthaneDichloroNickel
• CAS NO: 14647-23-5
• Molecular Formula: C₂₆H₂₄P₂*Cl₂Ni
• Molecular Weight: 528.02
• EINECS: 1312995-182-4
• Product Categories: Ni;Metal Compounds;API intermediates;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Ni (Nickel) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysis and Inorganic Chemistry;Chemical Synthesis;metal-phosphine complexes
• Mol File: 14647-23-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 263-265 °C(lit.)
• Boiling Point: 514.8 °C at 760 mmHg
• Flash Point: 281.7 °C
• Appearance: orange/crystal
• Vapor Pressure: 3.38E-10mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Sparingly)
• Water Solubility: insoluble
• CAS DataBase Reference: 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride(14647-23-5)
• EPA Substance Registry System: 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride(14647-23-5)

Safety Data

• Hazard Codes: T,Xn
• Statements: 45-20/21/22-36/37/38-42/43-40
• Safety Statements: 53-22-26-36-45-52
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 14647-23-5(Hazardous Substances Data)

Usage

Chemical Properties

Orange to red crystalline powder

Uses

Different sources of media describe the Uses of 14647-23-5 differently. You can refer to the following data:
1. suzuki reaction
2. Dichloro[bis(1,2-diphenylphosphino)ethane]nickel(II) is a reactant involved in Kumada catalyst-transfer polycondensation, oxidation of carboranyl phosphine ligands, synthesis of nickel-iron dithiolato hydrides, Ullmann reactions - homocoupling reactions, co-catalyst for hydroformylation of alcohols for the synthesis of quaternary carbon centers, catalyst for Wacker-type intramolecular aerobic oxidative amination of alkenes.

InChI:InChI=1/C26H24P2.2ClH.Ni/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26;;;/h1-20H,21-22H2;2*1H;/q;;;+2/p-2

Synthetic route

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2) + chlorine (7782-50-5) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 3-chloropropanoic anhydride (20495-99-2) + [(1,2-bis(diphenylphosphino)ethaneO2)3Ni][NiCl4]

Conditions	Yield
In dichloromethane at -196.16℃; for 14h; Glovebox; Sealed tube;	A 100% B 96% C 75%

nickel(II) chloride hexahydrate + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
In ethanol at 80℃; for 0.5h; Sealed tube; Inert atmosphere;	98%
In methanol; isopropyl alcohol for 0.5h;	93%
In methanol; isopropyl alcohol equimolar amounts; stirring for 30 min;; filtration; recrystn. from hot acetone; elem. anal.;;	>75

nickel(II) chloride dihydrate + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
With acetic acid In water for 10h; Heating;	95%

dimethylnickel{1,2-bis(diphenylphosphino)ethane} (31387-22-1) + propionyl chloride (79-03-8) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + methane (34557-54-5) + ethane (74-84-0) + ethene (74-85-1) + acetone (67-64-1)

Conditions	Yield
In toluene toluene and EtCOCl added to Ni complex at -196°C, after evacuation stirred at room temp. for 24 h; ppt. collected by filtration, crystd. from THF-Et2O; GLC anal.;	A 88% B 51% C 8% D 15% E 21%

NiCl3(bis(diphenylphosphino)ethane) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
In acetonitrile at 25℃; under 20 Torr; Solvent; Photolysis;	87%

2,3,4,5-tetraphenylnickelole-bis(1,2-diphenylphosphino)ethane + diphenyl acetylene (501-65-5) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + hexaphenylbenzene (992-04-1)

Conditions	Yield
With hydrogenchloride In toluene under anhyd. and O2-free N2; refluxed (18 h); 6 N HCl added; ppt. filtered off; org. filtrate washed (aq. NaHCO3); dried (anhyd. MgSO4); evapd.;	A n/a B 60%

dimethylnickel{1,2-bis(diphenylphosphino)ethane} (31387-22-1) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + ethane (74-84-0) + NiPh(Cl)(1,2-bis(diphenylphosphino)ethane) (88544-62-1) + NiCl(Me)(1,2-bis(diphenylphosphino)ethane) (88544-61-0) + toluene (108-88-3)

Conditions	Yield
With chlorobenzene In neat (no solvent) mixt. of educt and PhCl stirred at room temp. for 5 d; hexane added, ppt. dissolved in THF, solid recovered by addn. of hexane; GLC, NMR anal.;	A n/a B 14% C n/a D 55% E 50%

(1,2-dimethoxyethane)dichloronickel(II) (29046-78-4) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;	54%
In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Glovebox;	219 mg

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + methanesulfonyl chloride (124-63-0) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (DPPE)NiCl(sulfonyl-O,O'-Me) + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4)

Conditions	Yield
In tetrahydrofuran inert atmosphere; addn. of DPPE to soln. of Ni(COD)2 in THF, cooling (-78°C), addn. of sulfonyl chloride, stirring (room temp.); filtn., pptn. on addn. of hexane, washing, drying; elem. anal.;	A 38% B 18% C n/a

1,2-bis-(diphenylphosphino)ethane (1663-45-2) + nickel dichloride → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
In not given
In N,N-dimethyl-formamide NiCl2 was reacted with dppe in DMF;
In ethanol in refluxing EtOHfor 15 min;

(DPPE)Ni(cycloocta-1,5-diene) (96055-24-2) + dimethylamino sulfonyl chloride (13360-57-1) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

1,2-bis(diphenylphosphinoyl)ethane (4141-50-8) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane / 1 h / 20 °C / Schlenk technique; Inert atmosphere; Sealed tube 2: hexachlorodisilane / dichloromethane-d2 / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox 3: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Glovebox View Scheme

C26H24Cl2P2(2+)*2Cl(1-) → 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: hexachlorodisilane / dichloromethane-d2 / 0.08 h / 20 °C / Inert atmosphere; Schlenk technique; Glovebox 2: dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Glovebox View Scheme

methyllithium lithium bromide + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (μ-PhPH)2Fe2(CO)6 → {μ-(Ph2PCH2CH2PPh2)Ni(PhP)2}Fe2(CO)6

Conditions	Yield
In tetrahydrofuran; diethyl ether; acetone (N2); to soln. of Fe- and LiMe/LiBr-complex in Et2O and THF added Ni complex at -78°C, then degassed acetone; mixt. was warmed up to room temp., after 1 h removed solvents in vac., leaving black solid.; chromy. (silicic acid/CH2Cl2); solvent removed, recrystn. from CH2Cl2/pentane; elem. anal.;	99%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + C2H3N*2ClO4(1-)*C36H44N8Ni3S4(2+) → 2ClO4(1-)*2H2O*C44H46N4Ni2P2S2(2+)

Conditions	Yield
Stage #1: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; C2H3N*2ClO4(1-)*C36H44N8Ni3S4(2+) In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1,2-bis-(diphenylphosphino)ethane In acetonitrile for 24h; Inert atmosphere; Stage #3: With sodium perchlorate In acetonitrile for 1h; Inert atmosphere;	95%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + diethyl ether (60-29-7) + C32H32Br4N8Ni3S4(2+)*2ClO4(1-)*2.5H2O → 2ClO4(1-)*0.75C4H10O*C42H40Br2N4Ni2P2S2(2+)

Conditions	Yield
Stage #1: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; C32H32Br4N8Ni3S4(2+)*2ClO4(1-)*2.5H2O In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With 1,2-bis-(diphenylphosphino)ethane In acetonitrile for 24h; Inert atmosphere; Stage #3: diethyl ether Further stages;	95%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (μ-dithio)bis(tricarbonyliron) + lithium triethylborohydride (22560-16-3) → {μ-(diphos)NiS2}Fe2(CO)6 (116888-32-5)

Conditions	Yield
In tetrahydrofuran; acetone under N2, to the stirred soln. of 2.91 mmol Fe compd. in THF cooled to -78°C was added LiEt3BH in THF in small portions, to this was added (diphos)NiCl2 and acetone, stirred for 6 h at -78°C, then warmed to room temp. over 1 h; solvent. evapd. in vac., chromy. (silicic acid-CH2Cl2), recrystd. from CH2Cl2;	93%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (μ-dithio)bis(tricarbonyliron) (14243-23-3) → {μ-(diphos)NiS2}Fe2(CO)6 (116888-32-5)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran (N2); (a) 1-2 equiv of LiB(C2H5)3H/THF added slowly to Fe complex soln., (b) treated with Ni complex in THF/acetone;	93%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + [Sn((CH2S5C3)2)(CH3)2] (470664-68-7) → [Ni(2-thioxo-1,3-dithiol-4,5-dithiolato)(bis(diphenylphosphino)ethane)] (96042-52-3)

Conditions	Yield
In acetone byproducts: cyclo-[S(CS)S2C2SCH2CH2SC2S2(CS)S]; Ni complex added to suspn. of Sn complex in acetone, stirred for 12 h; solvent removed in vacuo, chromy. (silica, hexane/acetone (2/1));	93%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + cadmium(II) diethyldithiocarbamate (14239-68-0) + dichloromethane (75-09-2) → (N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorocadmate*0.5(dichloromethane)

Conditions	Yield
In acetonitrile refluxed for 1 h; filtered, evapd. to dryness (vac.), repptd. (dichloromethane/diethyl ether), ppt. filtered, washed (diethyl ether), dried (vac.); elem. anal.;	93%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + bis(N,N-diethyldithiocarbamato)zinc(II) (14324-55-1) → (N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorozincate

Conditions	Yield
In acetonitrile refluxed for 1 h; filtered, evapd. to dryness (vac.), repptd. (dichloromethane/diethyl ether), ppt. filtered, washed (diethyl ether), dried (vac.); elem. anal.;	93%

pentachlorothiophenol (133-49-3) + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) → C38H24Cl10NiP2S2

Conditions	Yield
Stage #1: pentachlorothiophenol With methyllithium In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; Schlenk technique; Stage #2: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether for 2h; Inert atmosphere; Schlenk technique;	93%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + disodium maleonitriledithiolato → (bis(1,2-diphenylphosphino)ethane)(maleonitriledithiolato)nickel(II) (81097-96-3)

Conditions	Yield
In acetone byproducts: NaCl; mixing equimolar amts. at 0°C, stirring and warming to room temp.(overnight); centrifugation, evapn. (vac.), chromy. (SiO2, CHCl3), crystn. on slow evapn.;	92.4%
In acetone byproducts: NaCl; acetone was added to a mixture of solid complex and salt, stirred for 30 min; filtration, pptn. by slow addition of water, filtration, washin a ppt. with diethyl ether, recrystn. (dichloromethane/diethyl ether); elem. anal.;

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + silver diethyldithiocarbamate (38351-46-1) → (N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) chloride + (N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) dichloroargenate

Conditions	Yield
In acetonitrile byproducts: AgCl; refluxed for 1 h; filtered (celite), evapd. to dryness (vac.), repptd. (dichloromethane/diethyl ether), ppt. filtered, washed (diethyl ether), dried (vac.); elem.anal.;	A n/a B 92%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + thallium(I) bis(3-tert-butylmercaptoimidazolyl)dihydroborate → [(1,2-bis(diphenylphosphino)ethane)Ni(.kappa(3)-S,S,H-bis(3-tert-butylmercaptoimidazolyl)dihydroborate)]Cl

Conditions	Yield
In dichloromethane byproducts: TlCl; 1 equiv. of Tl-compd. suspn. in CH2Cl2 was added to Ni-compd. soln. in CH2Cl2, stirring for 15 min; soln. was filtered, concd. in vac., pentane was added, solid was filtered off, dried in vac. for 3 h, elem. anal.;	92%

hexamethylcyclotrisilathiane (3574-04-7) + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + methyllithium (917-54-4) → Ni(SSiMe3)2(1,2-diphenylphosphino)ethane) (379262-18-7)

Conditions

Yield

In tetrahydrofuran; diethyl ether under inert atm. soln. (Me2SiS)3 in Et2O was treated with soln. MeLi in Et2O, stirred at 0°C for 5 min, and added to suspn. NiCl2(dppe) in THF and stirred at 0°C for 10 min, THF was added and stirred at0°C for 15 min; soln. was evapd., residue was extd. with toluene and centrifuged, soln. was concd., hexane was added, ppt. was filtered and washed with hexane; elem. anal.;

92%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (CH3C5H4)2TiS4P2(C6H4OCH3)2 (90432-13-6) → dichlorobis(η5-methylcyclopentadienyl)titanium(IV) (1282-40-2) + NiS3P(C6H4OCH3)(P(C6H5)2(CH2)2P(C6H5)2) (90413-02-8)

Conditions	Yield
In tetrahydrofuran byproducts: (C6H4OCH3PS)3; The soln. of reagents in THF was stirred for 20 h (N2 atm.);; evapd., recrystd. by dilution of CH2Cl2 soln. with methanol; elem. anal.;;	A n/a B 91%

3-thiapentan-1,5-dithiol (3570-55-6) + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 (86991-88-0) + 2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi → C40H47FeNiP2S3(1+)*F6P(1-)

Conditions	Yield
Stage #1: 3-thiapentan-1,5-dithiol; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; 2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 In tetrahydrofuran; hexane Inert atmosphere; Schlenk technique;	90%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 3,5-dichlorothiophenol (17231-94-6) → C38H30Cl4NiP2S2

Conditions	Yield
Stage #1: 3,5-dichlorothiophenol With methyllithium In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere; Schlenk technique; Stage #2: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; diethyl ether for 2h; Inert atmosphere; Schlenk technique;	90%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + tris(N,N-diethyldithiocarbamato)manganese(III) (15740-71-3) + dichloromethane (75-09-2) → (N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachloromanganate(II)*dichloromethane

Conditions	Yield
In acetonitrile byproducts: tetraethylthiuram disulfide; refluxed for 1 h; filtered, evapd. to dryness (vac.), repptd. (dichloromethane/diethyl ether), ppt. filtered, washed (diethyl ether), dried (vac.); elem. anal.;	89%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + [NEt4][Fe(N(CH2CH2S)3)(NO)] + acetonitrile (75-05-8) → [(Fe(N(CH2CH2S)3)(NO)-S,S')NiCl(dppe)]*CH3CN

Conditions	Yield
In acetonitrile under N2 atm. to stirred suspn. (NiCl2(dppe)) in MeCN was added soln. (NEt4)(Fe(N(CH2CH2S)3)(NO)) in MeCN; after standing overnight, ppt. was filtered and dried; elem. anal.;	88%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + C9H13NO2S3 → Ni[(SCH2)2NTs](dppe)

Conditions	Yield
With sodium ethanolate In ethanol; dichloromethane for 3h;	88%

carbon disulfide (75-15-0) + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + (2-cyanophenyl)acetonitrile (3759-28-2) → [Ni(1,2-bis(diphenylphosphino)ethane)(2-cyanobenzylcyanidedithiolate)]

Conditions	Yield
Stage #1: (2-cyanophenyl)acetonitrile With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: carbon disulfide In tetrahydrofuran for 2h; Inert atmosphere; Stage #3: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran; dichloromethane at 20℃; for 24h; Inert atmosphere;	88%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 (86991-88-0) + (LiSCH2CH2)2O·2THF + bis(2-mercaptoethyl)ether (2150-02-9) → C40H47FeNiOP2S2(1+)*F6P(1-)

Conditions	Yield
Stage #1: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; (LiSCH2CH2)2O·2THF; bis(2-mercaptoethyl)ether With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: [(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6 In tetrahydrofuran; hexane Inert atmosphere; Schlenk technique;	88%

1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + sodium trimethylsilanethiolate (87495-22-5) → Ni(dppe)(SSiMe3)2 (379262-18-7)

Conditions	Yield
In tetrahydrofuran (N2); standard air-sensitive technique; NaSSiMe3 (2.2 equiv.) was added to stirred suspn. of Ni complex in THF; suspn. was stirred for 20 min; solvent removed (vac.); extd. (ether); filtered through Celite; hexane added; crystd. (-30°C); elem. anal.;	87%

ammonium hexafluorophosphate + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 2-mesityl isocyanide (57116-96-8) → [Ni(1,2-bis(diphenylphosphino)ethane)(mesityl isocyanide)3](PF6)2

Conditions	Yield
In dichloromethane; acetone addn. of mixt. of 3 equiv. of isocyanide and excess NH4PF6 (in CH2Cl2/Me2CO=1:1) to Ni-complex soln. (in CH2Cl2/Me2CO=3:1), stirring for 2 h; solvent removal, extn. into CH2Cl2; elem. anal.;	87%

ammonium hexafluorophosphate + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 1,4,7-trithiacyclononane (6573-11-1) → {Ni((SC2H4)3)2}(2+)*2PF6(1-)={Ni((SC2H4)3)2}{PF6}2 + {Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}(2+)*2PF6(1-)={Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}{PF6}2

Conditions	Yield
In methanol react. of Ni complex with cyclononane (1 molar equivalent) in refluxing methanol; addn. of NH4PF6, refluxing, pptn.; fractional recrystn. from CH3CN-diethyl ether (removal of (Ni((9)aneS3)2)(PF6)); elem. anal.;	A n/a B 86%

thallium(I) hexafluorophosphate + 1,2-bis(diphenylphosphino)ethane nickel(II) chloride (14647-23-5) + 1,4,7-trithiacyclononane (6573-11-1) → {Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}(2+)*2PF6(1-)={Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}{PF6}2

Conditions	Yield
In nitromethane react. of Ni complex with cyclononane (1 molar equivalent) in nitromethane at 293K in the presence of TlPF6 (2 molar equivalents);; filtration; addn. of diethyl ether, crystn.; elem. anal.;	86%

Upstream product

• 983-81-3 trans-1,2-bis(diphenylphosphino)ethylene 
• 29046-78-4 dichloronickel(1,2-dimethoxyethane) 
• 1663-45-2 1,2-bis-(diphenylphosphino)ethane 
• 83864-14-6 nickel dichloride 
• 31387-22-1 dimethylnickel{1,2-bis(diphenylphosphino)ethane} 
• 79-03-8 propionyl chloride 
• 96055-24-2 (DPPE)Ni(cycloocta-1,5-diene) 
• 13360-57-1 dimethylamino sulfonyl chloride 
• 501-65-5 diphenyl acetylene 
• 7782-50-5 chlorine 
• 15629-91-1 {NiJ₂-1.2-Bis-diphenylphosphino-aethan} 
• 19615-85-1 {NiJ₂-(1.2-Bis-diphenylphosphino-aethan)2} 
• 19615-83-9 {NiBr₂-(1.2-Bis-diphenylphosphino-aethan)2} 
• 14647-21-3 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 

Downstream Products

• 535969-39-2 7-isopropylindene 
• 79361-89-0 (η-5C5H5)Ni(dppe) 
• 113572-50-2 {Ni(ethylenebis(dithiocarbamate))(dppe)} 
• 115677-85-5 (phenyl)nickel(II)bromide{1,2-bis(diphenylphosphino)ethane} 
• 15628-25-8 Ni⁽⁰⁾(1,2-bis(diphenylphosphino)ethane)2 
• 15793-01-8 Ni(CO)2{1,2-bis(diphenylphosphino)ethane} 
• 75-77-4 chloro-trimethyl-silane 
• 96555-94-1 (((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Ni)2P₂ 
• 110305-32-3 (((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Ni(PSi(CH₃)3)2) 
• 17446-52-5 trimethylphosphinosilane 
• 7803-51-2 phosphan 
• 115746-73-1 ((C₆H₅)2PCH₂CH₂P(C₆H₅)2)Ni((CH₃)3SiPPC(CH₃)3) 
• 116888-32-5 {μ-(diphos)NiS2}Fe2(CO)6 

Relevant articles and documents

Catecholato complexes of cobalt and nickel with 1,4-disubstituted-1,4-diazabutadiens-1,3 and 1,2-bis(diphenylphosphino)ethane

Divalent cobalt and nickel form four-coordinate complexes with sterically hindered 3,6-di-tert-butylcatecholato dianion (3,6-DBCat) and neutral bidentate 1,4-disubstituted-1,4-diazabutadiens-1,3 (DAB). Structural study of (1,4-di-tert-butyl-1,4-diazabutadiene-1,3)(3,6-di-tert-butyl-catecolato)nickel and (1,4-bis-(2,6-di-iso-propylphenyl)-2,3-dimethyl-1,4-diazabutadiene-1,3)(3,6-di-tert-butyl-catecolato)cobalt indicates square-planar environment of metals. Chemical one-electron oxidation of nickel complexes proceeds through catecholate ligand and leads to o-semiquinonato adducts. EPR spectral parameters indicate preservation of square-planar configuration after oxidation. Complexes (DAB)M(Cat) (M = Ni, Co) undergo neutral ligand substitution reactions. [Figure not available: see fulltext.]

Kinetics of the Homogeneous and Heterogeneous Coupling of Furfural with Biomass-Derived Alcohols

The tandem dehydrogenation and aldol condensation of butanol with furfural was investigated over homogeneous and heterogeneous catalysts using kinetics and isotope effects. In the homogeneous system, Ni(dppe)Cl2 catalyzes the transfer dehydrogenation of butanol to the furfural, whereas the aldol condensation of butyraldehyde and furfural takes place over the basic K2CO3 cocatalyst. In the heterogeneous system, a transition-metal-free mixed Mg–Al oxide, both the transfer hydrogenation and aldol condensation take place over the basic sites of the catalyst, and the rate-determining step is the alpha-hydride transfer from the butanol to the furfural.

A new polymorph, form C, of [1,2-bis(diphenylphosphino)ethane]-dichloronickel(II)

The title compound, [NiCl2(C26H24P2)], has arisen as a result of the unexpected reduction (hydrogenation) of the trans-1.2-bis(diphenylphosphino)ethene ligand. The hydrothermal reaction conditions have produced a third polymorphic form of the compound which has twofold symmetry, crystallizes in an enantiomer-selective manner and contains an unexpectedly short C-C (ethane) bond. Contacts of the form C-H···Cl are present, one involving alkyl and the other aryl hydrogen, with C···Cl distance of 3.556 (4) and 3.664 (6) A, respectively.

Efficient catalytic transfer hydrogenation reactions of carbonyl compounds by Ni(II)-diphosphine complexes

The catalytic transfer hydrogenation reactions of a series of aromatic and aliphatic carbonyl compounds were investigated using divalent Ni(II)-diphosphine complexes, [L2NiCl2] (where L2 = 1,1-bis(diphenylphosphino)methane (dppm), 1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), 1,1-bis(diphenylphosphino)ferrocene (dppf), and N-butyl-N-(diphenylphosphino)-1,1-diphenylphosphinamine (dppba)). This is a single-step reaction in the presence of potassium hydroxide and isopropyl alcohol to afford the corresponding alcohols. This protocol tolerates other sensitive functional groups like olefinic double bonds and also achieves high chemoselectivity. All the reactions were monitored by GC and GC–MS. The plausible mechanism is also discussed. The method reported in the present article is simple, cost-effective, and provides excellent conversions. Nickel-diphosphine complexes appear as a potential alternative to expensive transition metal complexes.