23582-06-1

Basic information

• Product Name: [2-(diphenylarsino)ethyl]diphenylphosphine
• Synonyms: [2-(diphenylarsino)ethyl]diphenylphosphine;OXOPHENYLARSINE(2-DIPHENYLARSINOETHYL)DIPHENYLPHOSPHINE;1-DIPHENYLPHOSPHINO-2-DIPHENYLARSINOETHANE;2-(diphenylphosphinoethyl)diphenylarsine;1-(Diphenylarsino)-2-(diphenylphosphino)ethane;Diphenyl[2-(diphenylphosphino)ethyl]arsine;Einecs 245-758-5
• CAS NO: 23582-06-1
• Molecular Formula: C₂₆H₂₄AsP
• Molecular Weight: 442.364121
• EINECS: 245-758-5
• Mol File: 23582-06-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 518.1°Cat760mmHg
• Flash Point: 283.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 2.52E-10mmHg at 25°C
• CAS DataBase Reference: [2-(diphenylarsino)ethyl]diphenylphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(diphenylarsino)ethyl]diphenylphosphine(23582-06-1)
• EPA Substance Registry System: [2-(diphenylarsino)ethyl]diphenylphosphine(23582-06-1)

Safety Data

• Hazardous Substances Data: 23582-06-1(Hazardous Substances Data)

Usage

General Description

[2-(diphenylarsino)ethyl]diphenylphosphine is an organophosphorus compound with the chemical formula C26H24AsP. It is a member of the organoarsenic and organophosphorus chemical families and is commonly used in the field of organometallic chemistry. [2-(diphenylarsino)ethyl]diphenylphosphine is known for its ability to act as a ligand in coordination chemistry, forming stable complexes with metal ions. In addition, [2-(diphenylarsino)ethyl]diphenylphosphine has been studied for its potential applications in catalysis, as well as in the synthesis of various organic and inorganic compounds. Its unique molecular structure and properties make it a valuable tool in both academic and industrial research.

InChI:InChI=1/C26H24AsP/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

Synthetic route

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) (12146-37-1, 124717-04-0) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → (1-diphenylphosphino-2-diphenylarsinoethane)molybdenum tetracarbonyl (53557-42-9) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0)

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

[Pd(3,4-Me2C6H2C(Me)=NN(H)(3'-(CF3)C4H2N2))Cl] (1174037-38-7) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) + sodium perchlorate + silver trifluoromethanesulfonate (2923-28-6) → [Pd(3,4-Me2C6H2C(Me)=NN(H)(3'-(CF3)C4H2N2))(PPh2(CH2)2AsPh2)]ClO4 (1174037-43-4)

Conditions	Yield
In acetone byproducts: AgCl; Ag salt was added to soln. of Pd complex in acetone; stirred for 4 h; filtered through Celite; P-As ligand was added to filtrate; stirred for 2 h; NaClO4 was added; stirred for 1 h; H2O added; filtered; dried (vac.); elem. anal.;	99%

ammonium hexafluorophosphate + chloro(η5-cyclopentadienyl)(1,10-phenanthroline)ruthenium(II) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → bis(η5-cyclopentadienyl)bis(1,10-phenanthroline)(μ-1-(diphenylphosphino)-2-(diphenylarsino)ethane)diruthenium(II) hexafluorophosphate (109011-10-1)

Conditions	Yield
In ethanol a suspn. of Ru-complex in EtOH was treated with an ethanol soln. of dppae under inert atmosphere, mixt. was heated under reflux for 20 min, filtered, cooled to room temp., a soln. of NH4PF6 in EtOH was added; ppt. was isolated by filtration, washed with Et2O; elem. anal.;	98%

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate (84651-76-3) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → cyclopentadienylnickel(diphenylphosphino(diphenylarsino)ethylidene) (85412-97-1) + cyclopenta-1,3-diene (542-92-7)

Conditions	Yield
In chloroform under Ar, Ni complex and ligand stirred in CHCl3 for 5 min; filtered, filtrate dropped in ether, filtered, dried in vac., elem. anal.;	A 93% B n/a

ammonium hexafluorophosphate + [Pd(5-(COH)C6H3C(H)N(cyclohexyl)-C2,N)(μ-Cl)]2 (174865-79-3) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Pd(4-(COH)C6H3C(H)=NCy-C2,N)(1-diphenylphosphino-2-diphenylarsinoethane-P,As)][PF6] (523977-74-4)

Conditions	Yield
In acetone ligand (2 equiv.) added to soln. of Pd complex in acetone; stirred at room temp. for 2 h; NH4PF6 (1 equiv.) added; stirred for 1 h; water added dropwise; stirred for 2 h; filtered; ppt. washed with water; dried in vac. over anhyd. CaCl2; recrystd. from CH2Cl2-n-hexane; elem. anal.;	88%

[Pd(CH2CMe2PtBu2)(μ-Cl)]2 + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → Pd(2+)*Cl(1-)*((CH3)3C)2PC4H8(1-)*(C6H5)2PCH2CH2As(C6H5)2=(PdCl(((CH3)3C)2PC(CH3)2CH2)((C6H5)2PCH2CH2As(C6H5)2))

Conditions	Yield
In benzene to stirred soln. (Pt2Cl2(Bu2tPCMe2CH2)2) in benzene added ape and react. mixt. stirred at 40°C for 5 h under N2 atm.; soln. concd., hexane added, solid filtered, washed with ether and vac. dried; elem. anal.;	86%

chloro(methyl)(1,5-cyclooctadiene)platinum(II) (50978-00-2) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → PtCH3Cl(C6H5)2AsCH2CH2P(C6H5)2

Conditions	Yield
In dichloromethane ligand was added to soln. of the Pt complex in CH2Cl2, mixt. stirred at room temp. for 1 h; concd., filtered, washed with hexane and ether, dried under reduced pressure; elem. anal.;	86%

ammonium hexafluorophosphate + [Pd(5-(COH)C6H3C(H)N(cyclohexyl)-C2,N)(μ-Cl)]2 (174865-79-3) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Pd(5-(COH)C6H3C(H)=NCy-C2,N)(1-diphenylphosphino-2-diphenylarsinoethane-P,As)][PF6] (521070-28-0)

Conditions	Yield
With silver trifluorosulfonate In acetone byproducts: AgCl; AgOSO2CF3 (1 equiv.) added to soln. of Pd complex in acetone; stirred for 1 h; filtered through Celite; ligand (2 equiv.) and NH4PF6 (3 equiv.) added to soln.; stirred for 12 h; filtered; ppt. recrystd. from CHCl3-n-hexane; elem. anal.;	86%

sodium tetrafluoroborate (13755-29-8) + [Pt(6-neo-pentyl-2,2'-bipyridine(1-)κC,κ2N,N')Cl] (308108-82-9) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Pt(C10H7N2CH2C(CH3)2CH2)(C6H5)2PCH2CH2As(C6H5)2](1+)*BF4(1-)=[[PtC10H7N2CH2C(CH3)2CH2](C6H5)2PCH2CH2As(C6H5)2](BF4) (507271-10-5)

Conditions	Yield
In acetone NaBF4 was added to Me2CO soln. of 1 equiv. of Pt- and 1 equiv. of P-compd., resp., mixt. was stirred in for 4 h; solvent was evapd. to dryness, residue was recrystd. from CH2Cl2/Et2O, elem. anal.;	84%

Rh(1,5-cyclooctadiene)(η3-2-Me-allyl) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [η3-(2-Me-C3H4)Rh(arphos)] (81178-02-1)

Conditions	Yield
In hexane; dichloromethane a soln. of ligand in CH2Cl2 was added a soln. of complex in hexane and stirred for 0.5 h, N2 atm.; evapn. in vac., repptn. from CH2Cl2 with hexane at -30°C; elem. anal.;	83%

hydrogenchloride (7647-01-0) + potassium perrhenate (10466-65-6) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → ReOCl3(1-diphenylphosphino-2-diphenylarsinoethane) (181574-50-5)

Conditions	Yield
In hydrogenchloride; propan-1-ol refluxing in concd. HCl/PrOH=1:7 v/v for 24 h (pptn.); collection (filtration), washing (EtOH), drying (vac.);	83%

(C5Me5)MoCo2(CO)8CCO2-iPr + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → {C5(CH3)5}MoCo2(CO)6CCO2CH(CH3)2((C6H5)2AsCH2CH2P(C6H5)2)

Conditions	Yield
In tetrahydrofuran soln. of MoCo2 complex and arphos in THF stirred at ambient temp. for 45 min under dry N2; chromy. (SiO2; ether/hexane, 10/90); elem. anal.;	82%

sodium tetrafluoroborate (13755-29-8) + PtCl(C10H7N2C(CH3)2) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → Pt(C10H7N2C(CH3)2)((C6H5)2AsCH2CH2P(C6H5)2)(1+)*BF4(1-)=[Pt(C10H7N2C(CH3)2)((C6H5)2PCH2CH2As(C6H5)2)]BF4

Conditions	Yield
In acetone addn. of 1 equiv. of ligand to Pt-complex soln., then addn. of excess NaBF4, stirring (room temp.); evapn., dissoln. in CH2Cl2, filtration, concn., crystn. on Et2O addn.; elem. anal.;	81.4%

rhenium (III) chloride + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → Re3Cl9(arphos)1.5

Conditions	Yield
In ethanol combining of Re3Cl9 and arphos as solids, addn. of ethanol, pptn.; elem. anal.;	80%

sodium tetrafluoroborate (13755-29-8) + [Pt(6-neo-pentyl-2,2'-bipyridine(1-)κC,κ2N,N')Cl] (308108-82-9) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Pt2(C10H7N2CH2C(CH3)2CH2)2(μ-(1-diphenylphosphino-2-diphenylarsinoethane))](BF4)2

Conditions	Yield
In acetone NaBF4, Pt-compd. and 0.5 equiv. of P-compd. were stirred in Me2CO soln.at room temp. for 1 d; solvent was evapd. to dryness, residue was recrystd. from CH2Cl2/Et2O, elem. anal.;	80%

silver(I) hexafluorophosphate (26042-63-7) + [Pd(CH2CMe2PtBu2)(μ-Cl)]2 + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → (Pd(((CH3)3C)2PC(CH3)2CH2)((C6H5)2PCH2CH2As(C6H5)2))(1+)*PF6(1-)=(Pd(((CH3)3C)2PC(CH3)2CH2)((C6H5)2PCH2CH2As(C6H5)2))PF6 (99279-36-4)

Conditions	Yield
In methanol; dichloromethane byproducts: AgCl; to stirred soln. (Pd2Cl2(But2PCMe2CH2)2) in CH2Cl2 added 2 equiv. AgPF6in methanol and mixt. stirred for 30 min, AgCl centrifuged and filtered, ape added and react. mixt. stirred at room temp. for 4 h under N2 atm.; soln. concd., ether added; elem. anal.;	78%

[Pt2((COMe)2H)2(μ-Cl)2] + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → trans-P-Pt-Cl-[Pt(COMe)Cl(1-(diphenylarsino)-2-(diphenylphosphino)ethane] (264142-17-8, 263870-12-8) + trans-P-Pt-COMe-[Pt(COMe)Cl(1-(diphenylarsino)-2-(diphenylphosphino)ethane)] (263870-12-8, 264142-17-8)

Conditions	Yield
In acetone byproducts: CH3CHO; arsinophosphinoethane deriv. was dropped in acetone to acetone soln. of Pt-complex at -30 °C (ratio 2:1), mixt. was slowly warmed up to room temp.; isomer ratio trans-P-Pt-Cl : trans-P-Pt-COMe = 9:1 (detn. by (13)P-NMR);crystn. of trans-P-Pt-Cl isomer within 12 h, filtration, dried in vac.;	A 78% B n/a

sodium tetrafluoroborate (13755-29-8) + PtCl(C10H7N2C(CH3)2) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Pt2(C10H7N2C(CH3)2)2(μ-Ph2PCH2CH2AsPh2)](BF4)2

Conditions	Yield
In acetone addn. of 0.5 equiv. of ligand to Pt-complex soln., then addn. of excessNaBF4, stirring (room temp., 3 h); evapn., dissoln. in CH2Cl2, filtration, concn., crystn. on Et2O addn.; elem. anal.;	76%

1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → C26H24AsF2P

Conditions	Yield
With Carbonyl fluoride In dichloromethane at 25℃;	75%

cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) + silver trifluoromethanesulfonate (2923-28-6) → [{Ru(2,2'-bipyridine)2Cl}2{μ-Ph2P(CH2)2AsPh2}][CF3SO3]2

Conditions	Yield
Stage #1: cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride; silver trifluoromethanesulfonate In acetone at 20℃; for 2h; Inert atmosphere; Stage #2: 1-diphenylarsino-2-diphenylphosphinoethane In ethanol; toluene at 20℃; for 456h; Sealed tube; Inert atmosphere;	74%

tetrakis(actonitrile)copper(I) hexafluorophosphate (64443-05-6) + {N(PPh3)2}2{Ru4(μ-H)2(CO)12} + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → Cu2Ru4H2*12CO*(C6H5)2AsCH2CH2P(C6H5)2=Cu2Ru4H2((C6H5)2As(CH2)2P(C6H5)2)(CO)12

Conditions	Yield
In dichloromethane under N2; Ru containing salt treated with Cu-complex at -30°C; stirred for 1 min; bidentate ligand added; warmed to ambient temp. with stirring; solvent removed (reduced pressure);; extn. (CH2Cl2:Et2O 1:4); extract filtered (Celite); solvent removed (reduced pressure); chromy. (Florisil, -20°C, CH2Cl2-light petroleum); crystn. (CH2Cl2-light petroleum), elem. anal.;;	72%

chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II) (92390-26-6) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → (η5-pentamethylcyclopentadienyl)ruthenium(II)chloro[(1-diphenylarsanyl-2-diphenylphosphanyl)ethylene]

Conditions

Yield

In tetrahydrofuran byproducts: cyclooctadiene; stirring a soln. of (C5Me5)Ru(COD)Cl and the ligand for 24 h, all manipulations under argon, nitrogen or vacuum contg. less than 1 ppm oxygen and water; filtn., removal of the solvent in vacuum, addn. of hexane and THF at -78°C, warming to 40°C, stirring for 15 min, filtn., standing at room temp. overnight, filtn., washing with hexane, drying in vacuum, elem. anal.;

72%

NEt4{Nb(CO)6} (82581-56-4) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [Nb(CO)4((C6H5)2P(CH2)2As(C6H5)2)2](1-) + [(C2H5)4N](1+)*[Nb(CO)4(C6H5)2As(CH2)2P(C6H5)2](1-)=[(C2H5)4N][Nb(CO)4(C6H5)2As(CH2)2P(C6H5)2] (83536-55-4)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under N2, about equimolar amts. of (Et4N)Nb(CO)6 and phosphine dissolved in THF, irradiated (UV, Duran filter) for 70 min; pptd. by stirring concd. soln. with heptane, ppt. filtered off, washed with THF/heptane, dried under high vac. (0.01 Torr, 5 h);	A n/a B 71%

Co3(CO)9CCO2(menthyl) (117707-13-8) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → (Ph2AsCH2CH2PPh2)Co3O2(CO)7CCO2(menthyl)

Conditions	Yield
In tetrahydrofuran stirred under N2; 15 min at 40°C, 30 min at room temp.; progress of reaction followed by TLC (ether/hexane: 15/85); chromd. (silica gel; ether/hexane: 15/85); elem. anal.;	69%

[Pd(5-(COH)C6H3C(H)N(cyclohexyl)-C2,N)(μ-Cl)]2 (174865-79-3) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [(Pd[4-(COH)C6H3C(H)=NCy-C2,N](Cl))2(μ-1-diphenylphosphino-2-diphenylarsinoethane)] (523977-71-1)

Conditions	Yield
In acetone ligand (1 equiv.) added to soln. of Pd complex in acetone; stirred at room temp. for 12 h; filtered; solid dried in vac.; recrystd. from CHCl3-n-hexane; elem. anal.;	68%

carbonylchlorohydridotris(triphenylphosphine)ruthenium(II) (157072-60-1, 166941-05-5, 16971-33-8, 61521-25-3) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → [RuHCl(CO)(P(C6H5)3)((C6H5)2PCH2CH2As(C6H5)2)]

Conditions	Yield
In toluene (N2); reflux (1.5 h); filtration, concn., pptn. with n-pentane, filtration, washing (CH2Cl2/n-pentane, then n-pentane), drying (vac.); elem. anal.;	66%

{N(PPh3)2}2{Ru4(μ-H)2(CO)12} + tetrakis(acetonitrile)silver(I) hexafluorophosphate (86728-82-7) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → Ag2Ru4H2*12CO*(C6H5)2AsCH2CH2P(C6H5)2=Ag2Ru4H2((C6H5)2As(CH2)2P(C6H5)2)(CO)12

Conditions	Yield
In dichloromethane under N2; Ru containing salt treated with Ag-complex at -30°C; stirred for 1 min; bidentate ligand added; warmed to ambient temp. with stirring; solvent removed (reduced pressure);; extn. (CH2Cl2:Et2O 1:4); extract filtered (Celite); solvent removed (reduced pressure); chromy. (alumina, -20°C, CH2Cl2-light petroleum); crystn. (CH2Cl2-light petroleum); elem. anal.;;	65%

{dicarbonylnitrosyl(cyclohexadienyl(phenyl))manganese}{PF6} + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → {(C6H5C6H6)Mn(NO)(CH2P(C6H5)2)(CH2As(C6H5)2)}(1+)*PF6(1-)={(C6H5C6H6)Mn(NO)(CH2P(C6H5)2)(CH2As(C6H5)2)}PF6 (142042-19-1)

Conditions	Yield
In dichloromethane Mn complex and ligand suspd. in CH2Cl2 and refluxed, color changed from yellow to reddish; after 5.5 h concd., pptn. with diethyl ether, extd. (overnight, Soxhlet, toluene), pptn. (room temp., CH3CN soln. layered with Et2O), elem. anal.;	65%

hexacarbonyl(μ-1,1,3,3-teramethyl-2-thiocarbonylcyclohexane)diiron (84433-24-9, 61793-17-7) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → hexacarbonyl(1-diphenylphosphino-2-diphenylarsinoethane)(μ-1,1,3,3-teramethyl-2-thiocarbonylcyclohexane)diiron(Fe-Fe) (128178-28-9) + pentacarbonyl(1-diphenylphosphino-2-diphenylarsinoethane)(μ-1,1,3,3-teramethyl-2-thiocarbonylcyclohexane)diiron(Fe-Fe) (128178-29-0)

Conditions	Yield
In hexane; toluene dropwise addn. of ligand in toluene to the Fe compd. in hexane under N2 and stirring at 20°C for 18 h; concn. (vac.), chromy. on silica gel, eluating with toluene-hexane, evapn. (vac.) and recrystn. from hexane; elem. anal.;	A 64% B 11%

carbonyldihydridotris(triphenylphosphine)ruthenium(II) (22337-78-6) + 1-diphenylarsino-2-diphenylphosphinoethane (23582-06-1) → RuH2(CO)P(C6H5)3(P(C6H5)2C2H4As(C6H5)2) (80515-25-9)

Conditions	Yield
In toluene A soln. of reagents in toluene was refluxed for 1.5 h (inert atm.);; elem. anal.;;	64%

Downstream Products

• 121445-48-5 (CH₃)3SiNP(C₆H₅)2CH₂CH₂As(C₆H₅)2 
• 53557-42-9 (1-diphenylphosphino-2-diphenylarsinoethane)molybdenum tetracarbonyl 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 125392-27-0 ((dadpe)pentacarbonylrhenium)tetrafluoroborate 
• 125392-25-8 ((dadpe)pentacarbonylrhenium)tetrafluoroborate 
• 78064-18-3 [Pt(C₆H₅)2((C₆H₅)2AsCH₂CH₂P(C₆H₅)2)] 
• 126493-13-8 {Os₂(MeCO₂)2(CO)4(bis(diphenylphosphino)ethane)}n 
• 126493-17-2 {Os₂(MeCO₂)(CO)4(1-diphenylarsino-2-diphenylphosphinoethane)2}PF₆ 
• 128178-28-9 hexacarbonyl(1-diphenylphosphino-2-diphenylarsinoethane)(μ-1,1,3,3-teramethyl-2-thiocarbonylcyclohexane)diiron(Fe-Fe) 
• 128178-29-0 pentacarbonyl(1-diphenylphosphino-2-diphenylarsinoethane)(μ-1,1,3,3-teramethyl-2-thiocarbonylcyclohexane)diiron(Fe-Fe) 
• 128844-72-4 {Ru2(CO)4(μ-O2CMe)2(Ph2As(CH2)2PPh2)}n 
• 134736-57-5 Cr(CO)3(η1-Ph2AsCH2CH2PPh2)(η2-Ph2AsCH2CH2PPh2) 

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