chlorine
A
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
B
3-chloropropanoic anhydride
Conditions | Yield |
---|---|
In dichloromethane at -196.16℃; for 14h; Glovebox; Sealed tube; | A 100% B 96% C 75% |
1,2-bis-(diphenylphosphino)ethane
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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 |
1,2-bis-(diphenylphosphino)ethane
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
Conditions | Yield |
---|---|
With acetic acid In water for 10h; Heating; | 95% |
dimethylnickel{1,2-bis(diphenylphosphino)ethane}
propionyl chloride
A
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
B
methane
C
ethane
D
ethene
E
acetone
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% |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
Conditions | Yield |
---|---|
In acetonitrile at 25℃; under 20 Torr; Solvent; Photolysis; | 87% |
diphenyl acetylene
A
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
B
hexaphenylbenzene
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}
A
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
B
ethane
C
NiPh(Cl)(1,2-bis(diphenylphosphino)ethane)
D
NiCl(Me)(1,2-bis(diphenylphosphino)ethane)
E
toluene
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)
1,2-bis-(diphenylphosphino)ethane
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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)
methanesulfonyl chloride
1,2-bis-(diphenylphosphino)ethane
A
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
C
1,5-dicyclooctadiene
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
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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)
dimethylamino sulfonyl chloride
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
1,2-bis(diphenylphosphinoyl)ethane
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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 |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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 |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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
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
diethyl ether
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
lithium triethylborohydride
{μ-(diphos)NiS2}Fe2(CO)6
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
(μ-dithio)bis(tricarbonyliron)
{μ-(diphos)NiS2}Fe2(CO)6
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
[Sn((CH2S5C3)2)(CH3)2]
[Ni(2-thioxo-1,3-dithiol-4,5-dithiolato)(bis(diphenylphosphino)ethane)]
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
cadmium(II) diethyldithiocarbamate
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
bis(N,N-diethyldithiocarbamato)zinc(II)
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
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
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
(bis(1,2-diphenylphosphino)ethane)(maleonitriledithiolato)nickel(II)
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
silver diethyldithiocarbamate
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
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
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
methyllithium
Ni(SSiMe3)2(1,2-diphenylphosphino)ethane)
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
(CH3C5H4)2TiS4P2(C6H4OCH3)2
A
dichlorobis(η5-methylcyclopentadienyl)titanium(IV)
NiS3P(C6H4OCH3)(P(C6H5)2(CH2)2P(C6H5)2)
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
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6
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
3,5-dichlorothiophenol
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
tris(N,N-diethyldithiocarbamato)manganese(III)
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
acetonitrile
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% |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; dichloromethane for 3h; | 88% |
carbon disulfide
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
(2-cyanophenyl)acetonitrile
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
[(η5-pentamethylcyclopentadienyl)iron(acetonitrile)3]PF6
bis(2-mercaptoethyl)ether
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
sodium trimethylsilanethiolate
Ni(dppe)(SSiMe3)2
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% |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
2-mesityl isocyanide
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% |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
1,4,7-trithiacyclononane
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% |
1,2-bis(diphenylphosphino)ethane nickel(II) chloride
1,4,7-trithiacyclononane
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% |
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
Hazard Codes: T,Xn
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
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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