Product Name

  • Name

    1,2-Bis(diphenylphosphino)ethane nickel(II) chloride

  • EINECS 629-489-4
  • CAS No. 14647-23-5
  • Article Data25
  • CAS DataBase
  • Density
  • Solubility insoluble in water
  • Melting Point 263-265 °C(lit.)
  • Formula C26H24Cl2NiP2
  • Boiling Point 514.8 °C at 760 mmHg
  • Molecular Weight 528.02
  • Flash Point 281.7 °C
  • Transport Information
  • Appearance Orange to red crystalline powder
  • Safety 53-22-26-36-45-52
  • Risk Codes 45-20/21/22-36/37/38-42/43-40
  • Molecular Structure Molecular Structure of 14647-23-5 (1,2-Bis(diphenylphosphino)ethane nickel(II) chloride)
  • Hazard Symbols ToxicT,HarmfulXn
  • Synonyms Nickel,dichloro[ethylenebis[diphenylphosphine]]-, cis- (8CI);Nickel,dichloro[1,2-ethanediylbis[diphenylphosphine]-P,P']-, (SP-4-2)-;1,2-Bis(diphenylphosphino)ethanenickel dichloride;Dichloro[1,2-ethanediylbis[diphenylphosphine]-P,P']nickel;Dichloro[ethylenebis[diphenylphosphine]]nickel;Nickel1,2-Bis(diphenylphosphino)ethane dichloride;1,2-Ethylenebis(diphenylphosphine)nickel dichloride;Dichloro[1,2-bis(diphenylphosphino)ethane]nickel(II);
  • PSA 27.18000
  • LogP -0.73980

Synthetic route

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2)

(1,2-bis(diphenylphosphino)ethane)Ni(C2H4CO2)

chlorine
7782-50-5

chlorine

A

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

B

3-chloropropanoic anhydride
20495-99-2

3-chloropropanoic anhydride

C

[(1,2-bis(diphenylphosphino)ethaneO2)3Ni][NiCl4]

[(1,2-bis(diphenylphosphino)ethaneO2)3Ni][NiCl4]

Conditions
ConditionsYield
In dichloromethane at -196.16℃; for 14h; Glovebox; Sealed tube;A 100%
B 96%
C 75%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
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

nickel(II) chloride dihydrate

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
With acetic acid In water for 10h; Heating;95%
dimethylnickel{1,2-bis(diphenylphosphino)ethane}
31387-22-1

dimethylnickel{1,2-bis(diphenylphosphino)ethane}

propionyl chloride
79-03-8

propionyl chloride

A

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

B

methane
34557-54-5

methane

C

ethane
74-84-0

ethane

D

ethene
74-85-1

ethene

E

acetone
67-64-1

acetone

Conditions
ConditionsYield
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)

NiCl3(bis(diphenylphosphino)ethane)

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; under 20 Torr; Solvent; Photolysis;87%
2,3,4,5-tetraphenylnickelole-bis(1,2-diphenylphosphino)ethane

2,3,4,5-tetraphenylnickelole-bis(1,2-diphenylphosphino)ethane

diphenyl acetylene
501-65-5

diphenyl acetylene

A

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

B

hexaphenylbenzene
992-04-1

hexaphenylbenzene

Conditions
ConditionsYield
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

dimethylnickel{1,2-bis(diphenylphosphino)ethane}

A

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

B

ethane
74-84-0

ethane

C

NiPh(Cl)(1,2-bis(diphenylphosphino)ethane)
88544-62-1

NiPh(Cl)(1,2-bis(diphenylphosphino)ethane)

D

NiCl(Me)(1,2-bis(diphenylphosphino)ethane)
88544-61-0

NiCl(Me)(1,2-bis(diphenylphosphino)ethane)

E

toluene
108-88-3

toluene

Conditions
ConditionsYield
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-dimethoxyethane)dichloronickel(II)

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
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

bis(1,5-cyclooctadiene)nickel (0)

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

A

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

B

(DPPE)NiCl(sulfonyl-O,O'-Me)

(DPPE)NiCl(sulfonyl-O,O'-Me)

C

1,5-dicyclooctadiene
5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
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

1,2-bis-(diphenylphosphino)ethane

nickel dichloride

nickel dichloride

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
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

(DPPE)Ni(cycloocta-1,5-diene)

dimethylamino sulfonyl chloride
13360-57-1

dimethylamino sulfonyl chloride

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

1,2-bis(diphenylphosphinoyl)ethane
4141-50-8

1,2-bis(diphenylphosphinoyl)ethane

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
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-)

C26H24Cl2P2(2+)*2Cl(1-)

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

Conditions
ConditionsYield
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

methyllithium lithium bromide

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

(μ-PhPH)2Fe2(CO)6

(μ-PhPH)2Fe2(CO)6

{μ-(Ph2PCH2CH2PPh2)Ni(PhP)2}Fe2(CO)6

{μ-(Ph2PCH2CH2PPh2)Ni(PhP)2}Fe2(CO)6

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

C2H3N*2ClO4(1-)*C36H44N8Ni3S4(2+)

C2H3N*2ClO4(1-)*C36H44N8Ni3S4(2+)

2ClO4(1-)*2H2O*C44H46N4Ni2P2S2(2+)

2ClO4(1-)*2H2O*C44H46N4Ni2P2S2(2+)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

diethyl ether
60-29-7

diethyl ether

C32H32Br4N8Ni3S4(2+)*2ClO4(1-)*2.5H2O

C32H32Br4N8Ni3S4(2+)*2ClO4(1-)*2.5H2O

2ClO4(1-)*0.75C4H10O*C42H40Br2N4Ni2P2S2(2+)

2ClO4(1-)*0.75C4H10O*C42H40Br2N4Ni2P2S2(2+)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

(μ-dithio)bis(tricarbonyliron)

(μ-dithio)bis(tricarbonyliron)

lithium triethylborohydride
22560-16-3

lithium triethylborohydride

{μ-(diphos)NiS2}Fe2(CO)6
116888-32-5

{μ-(diphos)NiS2}Fe2(CO)6

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

{μ-(diphos)NiS2}Fe2(CO)6
116888-32-5

{μ-(diphos)NiS2}Fe2(CO)6

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

[Sn((CH2S5C3)2)(CH3)2]
470664-68-7

[Sn((CH2S5C3)2)(CH3)2]

[Ni(2-thioxo-1,3-dithiol-4,5-dithiolato)(bis(diphenylphosphino)ethane)]
96042-52-3

[Ni(2-thioxo-1,3-dithiol-4,5-dithiolato)(bis(diphenylphosphino)ethane)]

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

cadmium(II) diethyldithiocarbamate
14239-68-0

cadmium(II) diethyldithiocarbamate

dichloromethane
75-09-2

dichloromethane

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorocadmate*0.5(dichloromethane)

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorocadmate*0.5(dichloromethane)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

bis(N,N-diethyldithiocarbamato)zinc(II)
14324-55-1

bis(N,N-diethyldithiocarbamato)zinc(II)

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorozincate

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachlorozincate

Conditions
ConditionsYield
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

pentachlorothiophenol

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

C38H24Cl10NiP2S2

C38H24Cl10NiP2S2

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

disodium maleonitriledithiolato

disodium maleonitriledithiolato

(bis(1,2-diphenylphosphino)ethane)(maleonitriledithiolato)nickel(II)
81097-96-3

(bis(1,2-diphenylphosphino)ethane)(maleonitriledithiolato)nickel(II)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

silver diethyldithiocarbamate
38351-46-1

silver diethyldithiocarbamate

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) chloride

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) chloride

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) dichloroargenate

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) dichloroargenate

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

thallium(I) bis(3-tert-butylmercaptoimidazolyl)dihydroborate

thallium(I) bis(3-tert-butylmercaptoimidazolyl)dihydroborate

[(1,2-bis(diphenylphosphino)ethane)Ni(.kappa(3)-S,S,H-bis(3-tert-butylmercaptoimidazolyl)dihydroborate)]Cl

[(1,2-bis(diphenylphosphino)ethane)Ni(.kappa(3)-S,S,H-bis(3-tert-butylmercaptoimidazolyl)dihydroborate)]Cl

Conditions
ConditionsYield
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

hexamethylcyclotrisilathiane

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

methyllithium
917-54-4

methyllithium

Ni(SSiMe3)2(1,2-diphenylphosphino)ethane)
379262-18-7

Ni(SSiMe3)2(1,2-diphenylphosphino)ethane)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

(CH3C5H4)2TiS4P2(C6H4OCH3)2
90432-13-6

(CH3C5H4)2TiS4P2(C6H4OCH3)2

A

dichlorobis(η5-methylcyclopentadienyl)titanium(IV)
1282-40-2

dichlorobis(η5-methylcyclopentadienyl)titanium(IV)

NiS3P(C6H4OCH3)(P(C6H5)2(CH2)2P(C6H5)2)
90413-02-8

NiS3P(C6H4OCH3)(P(C6H5)2(CH2)2P(C6H5)2)

Conditions
ConditionsYield
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

3-thiapentan-1,5-dithiol

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6
86991-88-0

[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6

2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi

2Li(1+)*SCH2CH2SCH2CH2S(2-)=LiSCH2CH2SCH2CH2SLi

C40H47FeNiP2S3(1+)*F6P(1-)

C40H47FeNiP2S3(1+)*F6P(1-)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

3,5-dichlorothiophenol
17231-94-6

3,5-dichlorothiophenol

C38H30Cl4NiP2S2

C38H30Cl4NiP2S2

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

tris(N,N-diethyldithiocarbamato)manganese(III)
15740-71-3

tris(N,N-diethyldithiocarbamato)manganese(III)

dichloromethane
75-09-2

dichloromethane

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachloromanganate(II)*dichloromethane

(N,N-diethyldithiocarbamato)[1,2-bis(diphenylphosphino)ethane]nickel(II) tetrachloromanganate(II)*dichloromethane

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

[NEt4][Fe(N(CH2CH2S)3)(NO)]

[NEt4][Fe(N(CH2CH2S)3)(NO)]

acetonitrile
75-05-8

acetonitrile

[(Fe(N(CH2CH2S)3)(NO)-S,S')NiCl(dppe)]*CH3CN

[(Fe(N(CH2CH2S)3)(NO)-S,S')NiCl(dppe)]*CH3CN

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

C9H13NO2S3

C9H13NO2S3

Ni[(SCH2)2NTs](dppe)

Ni[(SCH2)2NTs](dppe)

Conditions
ConditionsYield
With sodium ethanolate In ethanol; dichloromethane for 3h;88%
carbon disulfide
75-15-0

carbon disulfide

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

(2-cyanophenyl)acetonitrile
3759-28-2

(2-cyanophenyl)acetonitrile

[Ni(1,2-bis(diphenylphosphino)ethane)(2-cyanobenzylcyanidedithiolate)]

[Ni(1,2-bis(diphenylphosphino)ethane)(2-cyanobenzylcyanidedithiolate)]

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6
86991-88-0

[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6

(LiSCH2CH2)2O·2THF

(LiSCH2CH2)2O·2THF

bis(2-mercaptoethyl)ether
2150-02-9

bis(2-mercaptoethyl)ether

C40H47FeNiOP2S2(1+)*F6P(1-)

C40H47FeNiOP2S2(1+)*F6P(1-)

Conditions
ConditionsYield
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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

sodium trimethylsilanethiolate
87495-22-5

sodium trimethylsilanethiolate

Ni(dppe)(SSiMe3)2
379262-18-7

Ni(dppe)(SSiMe3)2

Conditions
ConditionsYield
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

ammonium hexafluorophosphate

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

2-mesityl isocyanide
57116-96-8

2-mesityl isocyanide

[Ni(1,2-bis(diphenylphosphino)ethane)(mesityl isocyanide)3](PF6)2

[Ni(1,2-bis(diphenylphosphino)ethane)(mesityl isocyanide)3](PF6)2

Conditions
ConditionsYield
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

ammonium hexafluorophosphate

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

1,4,7-trithiacyclononane
6573-11-1

1,4,7-trithiacyclononane

A

{Ni((SC2H4)3)2}(2+)*2PF6(1-)={Ni((SC2H4)3)2}{PF6}2

{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

{Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}(2+)*2PF6(1-)={Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}{PF6}2

Conditions
ConditionsYield
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

thallium(I) hexafluorophosphate

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

1,2-bis(diphenylphosphino)ethane nickel(II) chloride

1,4,7-trithiacyclononane
6573-11-1

1,4,7-trithiacyclononane

{Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}(2+)*2PF6(1-)={Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}{PF6}2

{Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}(2+)*2PF6(1-)={Ni(C6H5)2PCH2CH2P(C6H5)2((SC2H4)3)}{PF6}2

Conditions
ConditionsYield
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%

1,2-Bis(diphenylphosphino)ethane nickel(II) chloride Chemical Properties

Systematic Name: Dichloronickel - ethane-1,2-diylbis(diphenylphosphane) (1:1)
Synonyms of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride (CAS NO.14647-23-5): 1,2-Bis(Diphenylphosphinoethane)nickel(II) chloride[Ni(dppe)Cl2] ; 1,2-Bis-(Diphenylphosphino EthaneDichloroNickel
CAS NO: 14647-23-5
Molecular Formula: C26H24Cl2NiP2
Molecular Weight: 528.02
Molecular Structure:
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 7
Polar Surface Area: 27.18 Å2
Flash Point: 281.7 °C
Enthalpy of Vaporization: 75.68 kJ/mol
Boiling Point: 514.8 °C at 760 mmHg
Vapour Pressure: 3.38E-10 mmHg at 25°C
Melting Point: 263-265 °C(lit.)
Storage temp: Refrigerator
Water Solubility: insoluble
Appearance: Orange to red crystalline powder
Product Categories of 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride (CAS NO.14647-23-5): 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

1,2-Bis(diphenylphosphino)ethane nickel(II) chloride Safety Profile

Hazard Codes: ToxicT,HarmfulXn
Risk Statements: 45-20/21/22-36/37/38-42/43-40
 R20/21/22: Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R42/43: May cause sensitization by inhalation and skin contact. 
R40: Limited evidence of a carcinogenic effect. 
R45: May cause cancer.
Safety Statements: 22-26-36-45-52-53
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S52: Not recommended for interior use on large surface areas. 
S53: Avoid exposure - obtain special instructions before use.
WGK Germany: 3

1,2-Bis(diphenylphosphino)ethane nickel(II) chloride Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. This chemical poses an explosion hazard. This material may become self-reactive and possibly explosive.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store 1,2-Bis(diphenylphosphino)ethane nickel(II) chloride (CAS NO.14647-23-5) in a cool, dry place. Store in a tightly closed container.

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