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1,4-Bis(diphenylphosphino)butane, also known as a phosphine ligand, is an organic compound that exists as a white to light yellow crystal powder. It is characterized by its phosphorus atoms bonded to two phenyl groups and a butane chain, which contributes to its unique chemical properties and reactivity.

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  • 7688-25-7 Structure
  • Basic information

    1. Product Name: 1,4-Bis(diphenylphosphino)butane
    2. Synonyms: [4-(Diphenylphosphino)butyl](diphenyl)phosphine;1,4-butanediylbis[diphenyl-phosphin;Bis(1,4-diphenylphosphino)butane;Phosphine, 1,4-butanediylbis[diphenyl-;1,4-bis(diphenylphosphino)butane(dppb);1,4-Bis(diphenyphosphino)Butane;1,4-Bis(diphenylphosphino)butane,98%DPPB;DPPB/1,4-BIS(DIPHENYLPHOSPHINO)BUTANE
    3. CAS NO:7688-25-7
    4. Molecular Formula: C28H28P2
    5. Molecular Weight: 426.47
    6. EINECS: 231-698-7
    7. Product Categories: Phosphines;Ligand;Phosphine Ligands;Synthetic Organic Chemistry;organophosphine ligand;Achiral Phosphine;Aryl Phosphine
    8. Mol File: 7688-25-7.mol
  • Chemical Properties

    1. Melting Point: 132-136 °C(lit.)
    2. Boiling Point: 542 °C at 760 mmHg
    3. Flash Point: 299.5 °C
    4. Appearance: White to almost white/Crystalline Powder
    5. Density: N/A
    6. Vapor Pressure: 2.92E-11mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. Water Solubility: Soluble in chloroform. Slightly soluble in water
    11. BRN: 706446
    12. CAS DataBase Reference: 1,4-Bis(diphenylphosphino)butane(CAS DataBase Reference)
    13. NIST Chemistry Reference: 1,4-Bis(diphenylphosphino)butane(7688-25-7)
    14. EPA Substance Registry System: 1,4-Bis(diphenylphosphino)butane(7688-25-7)
  • Safety Data

    1. Hazard Codes: Xi,F
    2. Statements: 36/38-36/37/38-11
    3. Safety Statements: 26-36-37/39-33-16-7/9
    4. WGK Germany: 3
    5. RTECS:
    6. F: 10-23
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 7688-25-7(Hazardous Substances Data)

7688-25-7 Usage

Uses

1,4-Bis(diphenylphosphino)butane is used as a ligand in various chemical reactions and applications due to its ability to form stable complexes with metal catalysts, enhancing their performance and selectivity.
Used in Organometallic Chemistry:
1,4-Bis(diphenylphosphino)butane is used as a ligand for alkylations, isomerization reactions, and other organometallic chemistry applications. Its presence improves the efficiency and selectivity of these reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Cross-Coupling Reactions:
1,4-Bis(diphenylphosphino)butane is used as a ligand in Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds. It plays an essential role in palladium(0)-catalyzed acylcyanation of arylacetylenes and deprotection of allyloxycarbamates, contributing to the formation of complex molecular structures.
Used in Heck Reaction:
In the Heck reaction, 1,4-Bis(diphenylphosphino)butane acts as a ligand, facilitating the formation of carbon-carbon bonds through the coupling of aryl or vinyl halides with alkenes in the presence of a palladium catalyst.
Used in Negishi Coupling:
1,4-Bis(diphenylphosphino)butane is used as a ligand in Negishi coupling, a cross-coupling reaction that involves the formation of carbon-carbon bonds between an organozinc reagent and an organic electrophile, such as an aryl or vinyl halide.
Used in Sonogashira Coupling:
In Sonogashira coupling, 1,4-Bis(diphenylphosphino)butane serves as a ligand, promoting the formation of carbon-carbon bonds between an aryl or vinyl halide and a terminal alkyne in the presence of a palladium catalyst.
Overall, 1,4-Bis(diphenylphosphino)butane is a versatile and essential ligand in various chemical reactions and applications, particularly in organometallic chemistry and cross-coupling reactions, due to its ability to enhance the performance and selectivity of metal catalysts.

Purification Methods

Recrystallise it from EtOH [Trippett J Chem Soc 4263 1961]. [King J Coord Chem 1 62 1971, Tolman Chem Rev 77 313 1977.]

Check Digit Verification of cas no

The CAS Registry Mumber 7688-25-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,6,8 and 8 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7688-25:
(6*7)+(5*6)+(4*8)+(3*8)+(2*2)+(1*5)=137
137 % 10 = 7
So 7688-25-7 is a valid CAS Registry Number.
InChI:InChI=1/C28H28P2/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22H,13-14,23-24H2

7688-25-7 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (B1246)  1,4-Bis(diphenylphosphino)butane  >98.0%(GC)

  • 7688-25-7

  • 5g

  • 565.00CNY

  • Detail
  • TCI America

  • (B1246)  1,4-Bis(diphenylphosphino)butane  >98.0%(GC)

  • 7688-25-7

  • 25g

  • 1,680.00CNY

  • Detail
  • Alfa Aesar

  • (B21122)  1,4-Bis(diphenylphosphino)butane, 98%   

  • 7688-25-7

  • 1g

  • 136.0CNY

  • Detail
  • Alfa Aesar

  • (B21122)  1,4-Bis(diphenylphosphino)butane, 98%   

  • 7688-25-7

  • 5g

  • 498.0CNY

  • Detail
  • Alfa Aesar

  • (B21122)  1,4-Bis(diphenylphosphino)butane, 98%   

  • 7688-25-7

  • 25g

  • 1760.0CNY

  • Detail
  • Alfa Aesar

  • (B21122)  1,4-Bis(diphenylphosphino)butane, 98%   

  • 7688-25-7

  • 500g

  • 23233.0CNY

  • Detail
  • Aldrich

  • (261947)  1,4-Bis(diphenylphosphino)butane  98%

  • 7688-25-7

  • 261947-5G

  • 369.72CNY

  • Detail
  • Aldrich

  • (261947)  1,4-Bis(diphenylphosphino)butane  98%

  • 7688-25-7

  • 261947-25G

  • 1,389.96CNY

  • Detail

7688-25-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-Bis(diphenylphosphino)butane

1.2 Other means of identification

Product number -
Other names 4-diphenylphosphanylbutyl(diphenyl)phosphane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7688-25-7 SDS

7688-25-7Synthetic route

1,4-bis(diphenylphosphinyl)butane
4151-27-3

1,4-bis(diphenylphosphinyl)butane

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 7h;95%
1,4-bis(diphenylphosphinyl)butan-1-one

1,4-bis(diphenylphosphinyl)butan-1-one

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With tetramethyldisilazane; isopropyl titanoate(IV) In methyl cyclohexane at 60℃;94%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

diphenylphosphane
829-85-6

diphenylphosphane

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 47h;87%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 47h;87%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

A

Tetraphenyldiphosphin
1101-41-3

Tetraphenyldiphosphin

B

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide In various solvent(s) Ambient temperature; elektrochemical reaction, anode Mg bar, cathode stainless steel; var. solv.; Yields of byproduct given;A n/a
B 85%
potassium diphenylphosphine
15475-27-1, 4346-39-8

potassium diphenylphosphine

(S)-2-(dibenzylamino)-3-phenyl-1-bromopropane
208103-10-0

(S)-2-(dibenzylamino)-3-phenyl-1-bromopropane

A

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

B

Dibenzyl-((S)-1-benzyl-2-diphenylphosphanyl-ethyl)-amine
208103-11-1

Dibenzyl-((S)-1-benzyl-2-diphenylphosphanyl-ethyl)-amine

Conditions
ConditionsYield
In tetrahydrofuran at -78 - -40℃;A 30%
B 64%
1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

A

(4-chlorobutyl)diphenylphosphane
79369-66-7

(4-chlorobutyl)diphenylphosphane

B

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
In tetrahydrofuran; toluene 1) -50 deg C, 2) 50 deg C;A 53%
B n/a
tetrachlorure d'octaphenyl-1,1,4,4,9,9,12,12 tetraphosphonia-1,4,9,12 cyclohexadecane
113237-54-0

tetrachlorure d'octaphenyl-1,1,4,4,9,9,12,12 tetraphosphonia-1,4,9,12 cyclohexadecane

A

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

B

1,4-bis(diphenylphosphinyl)butane
4151-27-3

1,4-bis(diphenylphosphinyl)butane

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 14h; Heating; Yield given. Yields of byproduct given;
1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

diphenylphosphane
829-85-6

diphenylphosphane

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With potassium hydroxide 1.) DMSO, 20 deg C, 2.) 50 deg C, 1 h; Yield given. Multistep reaction;
triphenylphosphine
603-35-0

triphenylphosphine

1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
With lithium In tetrahydrofuran at 0℃; for 0.5h;
tetrachlorure d'octaphenyl-1,1,6,6,9,9,14,14 tetraphosphonia-1,6,9,14 cyclohexadecadiene-3,11
113237-53-9

tetrachlorure d'octaphenyl-1,1,6,6,9,9,14,14 tetraphosphonia-1,6,9,14 cyclohexadecadiene-3,11

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr
2: 5N NaOH / aq. ethanol / 14 h / Heating
View Scheme
1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / toluene / 4 h / Heating
2: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr
3: 5N NaOH / aq. ethanol / 14 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 80 percent / toluene / 96 h / Heating; var. conc. and time
2: 95 percent / Hydrogen / Raney-Ni / 2.5 h / 20 °C / 41253.3 Torr
3: 5N NaOH / aq. ethanol / 14 h / Heating
View Scheme
iodo(cyclopentadienyl)dicarbonylruthenium(II)

iodo(cyclopentadienyl)dicarbonylruthenium(II)

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

(η5-C5H5)(CO)I(P(OMe)3)ruthenium(II)

(η5-C5H5)(CO)I(P(OMe)3)ruthenium(II)

B

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
pentamethylcyclopentadienyliron(III) dicarbonyl dimer In toluene under N2; soln. of Ru complex and 1 equiv of ligand in toluene heated to 105-110 °C, added catalyst, completion of react. detected by IR; cooled, evapd., sepd. by chromy. (SiO2, benzene), recrystd. from toluene/hexane; elem. anal.;
RuCl2(η6-p-cymene)(η1-dppb)

RuCl2(η6-p-cymene)(η1-dppb)

A

[RuCl2(η6-p-cymene)]2(μ-dppb)
853907-92-3

[RuCl2(η6-p-cymene)]2(μ-dppb)

B

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
In dichloromethane-d2 at 25℃; Equilibrium constant; Inert atmosphere; Schlenk technique;
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Conditions
ConditionsYield
Stage #1: 1,4-dibromo-butane With iodine; magnesium In tetrahydrofuran for 3h; Inert atmosphere;
Stage #2: chloro-diphenylphosphine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(1,4-bis(diphenylphosphino)butane)molybdenum tetracarbonyl
15553-69-2

(1,4-bis(diphenylphosphino)butane)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

C15H15BrO4

C15H15BrO4

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

C2H3O2(1-)*C54H50Br2O4P2

C2H3O2(1-)*C54H50Br2O4P2

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1h;100%
hexafluoro-1,4-naphthoquinone
1024-60-8

hexafluoro-1,4-naphthoquinone

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

3,3'-(butane-1,4-diylbis(diphenylphosphonionediyl))bis(5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olate)

3,3'-(butane-1,4-diylbis(diphenylphosphonionediyl))bis(5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olate)

Conditions
ConditionsYield
With air In water; dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere;100%
(S)-(-)-2-naphthyl-3-trifluoromethanesulfonyloxybiphenyl
170647-29-7, 173300-95-3

(S)-(-)-2-naphthyl-3-trifluoromethanesulfonyloxybiphenyl

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(S)-(+)-2-naphthyl-3-diphenylphosphinylbiphenyl
170647-33-3

(S)-(+)-2-naphthyl-3-diphenylphosphinylbiphenyl

Conditions
ConditionsYield
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium diacetate In dimethyl sulfoxide99%
carbonylgold(I) chloride
50960-82-2

carbonylgold(I) chloride

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

1,4-bis(diphenylphosphino)butane digold(I) dichloride
63640-04-0

1,4-bis(diphenylphosphino)butane digold(I) dichloride

Conditions
ConditionsYield
In benzene byproducts: CO; soln. of Ph2PCH2CH2CH2CH2PPh2 dropped to soln. of (OC)AuCl at 20°C under dry N2, stirred for 1 h (CO removed); filtered;99%
Pt(Sn(CH3)3)2(P(CH3C6H4)3)2

Pt(Sn(CH3)3)2(P(CH3C6H4)3)2

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

Pt(Sn(CH3)3)2(C6H5)2P(CH2)4P(C6H5)2

Pt(Sn(CH3)3)2(C6H5)2P(CH2)4P(C6H5)2

Conditions
ConditionsYield
99%
benzene ruthenium(II) dichloride dimer

benzene ruthenium(II) dichloride dimer

ethylenediamine
107-15-3

ethylenediamine

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(dppb)RuCl2(enethylenediamine)
1158920-26-3, 200259-42-3

(dppb)RuCl2(enethylenediamine)

Conditions
ConditionsYield
Stage #1: benzene ruthenium(II) dichloride dimer; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 120℃; for 1.5h;
Stage #2: ethylenediamine In dichloromethane at 40℃; for 1.5h;
99%
hydrogenchloride
7647-01-0

hydrogenchloride

palladium
7440-05-3

palladium

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride
29964-62-3

[1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride

Conditions
ConditionsYield
Stage #1: hydrogenchloride; palladium With nitric acid In water
Stage #2: 1,4-di(diphenylphosphino)-butane In water; N,N-dimethyl-formamide at 50℃; for 1h;
98.9%
bis(1,5-cyclooctadiene)diiridium(I) dichloride
12112-67-3

bis(1,5-cyclooctadiene)diiridium(I) dichloride

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

IrCl(1,5-cyclooctadiene)(1,4-bis(diphenylphosphino)butane)
688063-92-5

IrCl(1,5-cyclooctadiene)(1,4-bis(diphenylphosphino)butane)

Conditions
ConditionsYield
With dimethyl 2,2-diallylmalonate In dichloromethane byproducts: cyclooctadiene; to a soln. of complex in CH2Cl2 was added diphosphine, then a soln. of 3equiv of diallyl ether in CH2Cl2, the mixt. was stirred at room temp. f or 3 h (inert atm.); volatiles were removed in vac., recrystd. from CH2Cl2/n-hexane; elem. anal.;98%
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
52462-29-0

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

A

[RuCl2(η6-p-cymene)]2(μ-dppb)
853907-92-3

[RuCl2(η6-p-cymene)]2(μ-dppb)

B

[(p-cymene)Ru(dppb)Cl](1+)

[(p-cymene)Ru(dppb)Cl](1+)

Conditions
ConditionsYield
In dichloromethane stirred for 4 h; filtered, solvent-removed; elem. anal.;A 98%
B 0%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

silver perchlorate

silver perchlorate

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Ag2(2,2'-bipyridyl)2(dppb)][ClO4]2

[Ag2(2,2'-bipyridyl)2(dppb)][ClO4]2

Conditions
ConditionsYield
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.;98%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

dimercaptomaleonitrile disodium salt hydrate

dimercaptomaleonitrile disodium salt hydrate

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(maleonitriledithilato)(1,4-bis(diphenylphosphino)butane)nickel(II)
81098-03-5

(maleonitriledithilato)(1,4-bis(diphenylphosphino)butane)nickel(II)

Conditions
ConditionsYield
In acetone mixt. of solids NiCl2*6H2O (1 mmol) and Ph2P(CH2)4P(Ph)2 (0.42 g) in acetone stirred for 1 h; pptd. by H2O addn. with stirring; ppt. filtered off; washed (H2O, EtOH, Et2O); dried at room temp.; elem. anal.;98%
dichloro(tetraethylcyclobutadiene)platinum(II)
56664-81-4

dichloro(tetraethylcyclobutadiene)platinum(II)

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(PtCl2(C4(C2H5)4))2((C6H5)2P(CH2)4P(C6H5)2)
217475-40-6

(PtCl2(C4(C2H5)4))2((C6H5)2P(CH2)4P(C6H5)2)

Conditions
ConditionsYield
In dichloromethane Ar-atmosphere; stirring Pt-complex with 0.5 equiv. of phosphine (room temp., 5-10 h); pptn. on Et2O addn., filtration, washing (Et2O), drying (vac.); elem. anal.;97%
dichloro(tetraethylcyclobutadiene)platinum(II)
56664-81-4

dichloro(tetraethylcyclobutadiene)platinum(II)

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

(C4(C2H5)4)PtCl((C6H5)2P(CH2)4P(C6H5)2)(1+)*Cl(1-)*CH2Cl2=[(C4(C2H5)4)PtCl((C6H5)2P(CH2)4P(C6H5)2)]Cl*CH2Cl2

(C4(C2H5)4)PtCl((C6H5)2P(CH2)4P(C6H5)2)(1+)*Cl(1-)*CH2Cl2=[(C4(C2H5)4)PtCl((C6H5)2P(CH2)4P(C6H5)2)]Cl*CH2Cl2

Conditions
ConditionsYield
In dichloromethane Ar-atmosphere; stirring Pt-complex with equimolar amt. of phosphine (room temp., 2-3 h); pptn. on Et2O addn., standing (overnight), filtration, washing (Et2O), drying (vac.);97%
[Pd(o-C6H4C=NCH=CHNMe)(μ-Cl)]2

[Pd(o-C6H4C=NCH=CHNMe)(μ-Cl)]2

sodium perchlorate

sodium perchlorate

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Pd(o-C6H4C=NCH=CHNMe)((C6H5)2P(CH2)4P(C6H5)2-P,P)]ClO4
202066-49-7

[Pd(o-C6H4C=NCH=CHNMe)((C6H5)2P(CH2)4P(C6H5)2-P,P)]ClO4

Conditions
ConditionsYield
In acetone N2-atmosphere; stirring equimolar amts. of Pd-complex and phosphine (room temp., 2 h), addn. of NaClO4, stirring for 2 h, addn. of H2O, stirringfor 4 h (pptn.); filtration, drying (vac.), recrystn. (CH2Cl2/hexane); elem. anal.;97%
RuBr2(P(C6H5)3)3
56586-92-6, 15709-75-8

RuBr2(P(C6H5)3)3

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

RuBr2(1,4-bis(diphenylphosphino)butane)(PPh3)
184014-42-4

RuBr2(1,4-bis(diphenylphosphino)butane)(PPh3)

Conditions
ConditionsYield
In further solvent(s) Ar-atmosphere; equimolar amts., stirring in CH2Br2 at room temp. for 2 h; vol. reduction, pptn. on EtOH addn., collection (filtration), washing (EtOH, hexanes), drying (vac.); elem. anal.;97%
tris(triphenylphosphine)ruthenium(II) chloride
15529-49-4, 41756-81-4

tris(triphenylphosphine)ruthenium(II) chloride

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Ru(dppp)2]Cl2

[Ru(dppp)2]Cl2

Conditions
ConditionsYield
In hexane for 2h; Reflux;97%
Ru(OAc)2(CO)(PPh3)2

Ru(OAc)2(CO)(PPh3)2

ethylenediamine
107-15-3

ethylenediamine

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Ru(acetate)(CO)(1,4-bis(diphenylphosphino)butane)(1,2-ethylendiamine)]acetate

[Ru(acetate)(CO)(1,4-bis(diphenylphosphino)butane)(1,2-ethylendiamine)]acetate

Conditions
ConditionsYield
Stage #1: Ru(OAc)2(CO)(PPh3)2; 1,4-di(diphenylphosphino)-butane In dichloromethane at 20℃; for 6h;
Stage #2: ethylenediamine In dichloromethane at 20℃; for 2h;
97%
3,4,5-tris(tetradecyloxy)benzyl chloride

3,4,5-tris(tetradecyloxy)benzyl chloride

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

3,4,5-tris(tetradecyloxy)1,4-bis(diphenylphosphonium chloride)butane

3,4,5-tris(tetradecyloxy)1,4-bis(diphenylphosphonium chloride)butane

Conditions
ConditionsYield
In chloroform at 61℃; for 65h; Inert atmosphere;97%
[Ru(η1-OAc)(η2-OAc)(PPh3)2(CO)]
142215-87-0, 38596-65-5, 52746-32-4, 61990-12-3

[Ru(η1-OAc)(η2-OAc)(PPh3)2(CO)]

ethylenediamine
107-15-3

ethylenediamine

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Ru(acetate)(CO)(1,4-bis(diphenylphosphino)butane)(1,2-ethylendiamine)]acetate

[Ru(acetate)(CO)(1,4-bis(diphenylphosphino)butane)(1,2-ethylendiamine)]acetate

Conditions
ConditionsYield
Stage #1: [Ru(η1-OAc)(η2-OAc)(PPh3)2(CO)]; 1,4-di(diphenylphosphino)-butane In dichloromethane at 20℃; for 6h; Inert atmosphere; Schlenk technique;
Stage #2: ethylenediamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique;
97%
formaldehyd
50-00-0

formaldehyd

rhodium(III) trichloride hydrate

rhodium(III) trichloride hydrate

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

RhCl(CO)(1,4-bis(diphenylphosphino)butane)
62795-67-9

RhCl(CO)(1,4-bis(diphenylphosphino)butane)

Conditions
ConditionsYield
In ethanol; water for 0.5h; Inert atmosphere; Reflux;96.6%
potassium tetrachloroplatinate

potassium tetrachloroplatinate

water
7732-18-5

water

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[PtCl2(dppb)]*2H2O

[PtCl2(dppb)]*2H2O

Conditions
ConditionsYield
In methanol; dichloromethane for 24h; Schlenk technique; Inert atmosphere; Reflux;96.3%
pentacarbonyl(acetonitrile)tungsten
15096-68-1

pentacarbonyl(acetonitrile)tungsten

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

A

{1,4-bis(diphenylphosphino)butane}tetracarbonyltungsten(0)
54111-75-0

{1,4-bis(diphenylphosphino)butane}tetracarbonyltungsten(0)

B

{W(CO)5}2(P(C6H5)2(CH2)4P(C6H5)2)
120950-72-3

{W(CO)5}2(P(C6H5)2(CH2)4P(C6H5)2)

Conditions
ConditionsYield
In toluene (W(CO)5(NCMe)) and diphosphine (molar ratio: 5:1) refluxed in toluene under nitrogen (2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR;A 4%
B 96%
In chloroform (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in CHCl3 under nitrogen (55°C, 2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR;A 87%
B 13%
In chloroform (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in CHCl3 under nitrogen (55°C, 2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR;A 76%
B 24%
In toluene (W(CO)5(NCMe)) and diphosphine (molar ratio: 2:1) refluxed in toluene under nitrogen (2-2.5 h), soln. filtered through cellulose, pumped to dryness; washing with hexane or chromy. (silica gel, benzene); 31P-NMR;A 43%
B 57%
[,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate

[,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

{Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}(1+)*BF4(1-)={Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}BF4
70196-23-5

{Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}(1+)*BF4(1-)={Rh((C6H5)2PCH2CH2CH2CH2P(C6H5)2)2}BF4

Conditions
ConditionsYield
In methanol; dichloromethane H2-atmosphere; stirring (room temp., 20 min), phosphine soln. (CH2Cl2) addn., stirring (2 h); evapn. (vac.);96%
dichloro(1,5-cyclooctadiene)platinum(ll)
12080-32-9

dichloro(1,5-cyclooctadiene)platinum(ll)

phosphoric acid monophenyl ester
701-64-4

phosphoric acid monophenyl ester

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

{Pt(O2P(O)OC6H5)((C6H5)2P(CH2)4P(C6H5)2)}*H2O

{Pt(O2P(O)OC6H5)((C6H5)2P(CH2)4P(C6H5)2)}*H2O

Conditions
ConditionsYield
With Ag2O In dichloromethane react. under dry N2, addn. of (C6H5)2P(CH2)4P(C6H5)2, phenyl dihydrogenphosphate (molar ratio = 1:1) and an excess of Ag2O to a stirred soln. of PtCl2(cycloocta-1,5-diene) in CH2Cl2, refluxing for 4 h, cooling; filtration,, evapg. the filtrate to dryness under reduced pressure, oily residue, dissolving the oil in CH2Cl2, addn. of light petroleum, crystn. on standing, recrystn. from CH2Cl2-light petroleum, drying in vac., elem. anal.;96%
dichloro(1,5-cyclooctadiene)platinum(ll)
12080-32-9

dichloro(1,5-cyclooctadiene)platinum(ll)

ammonium hexafluorophosphate

ammonium hexafluorophosphate

2,6-dimethylphenyl isonitrile
119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[(1,4-bis(diphenylphosphino)butane)(2,6-dimethylphenyl isocyanide)platinum(II)](PF6)2*0.5dichloromethane

[(1,4-bis(diphenylphosphino)butane)(2,6-dimethylphenyl isocyanide)platinum(II)](PF6)2*0.5dichloromethane

Conditions
ConditionsYield
In dichloromethane; acetone under N2; successive addn. of diphosphine, isocyanide and excess of NH4PF6 to Pt-compd. dissolved in CH2Cl2 and acetone, stirring at room temp.for 2 h; evapn. of solvent to dryness under reduced pressure, extn. of residue with CH2Cl2, washing with H2O and drying over Na2SO4, concg. of soln., crystn. by addn. of Et2O; elem. anal.;96%
[Pd(μ-N3)(2-(2'-thienyl)pyridine(-H))]2
1190631-16-3

[Pd(μ-N3)(2-(2'-thienyl)pyridine(-H))]2

1,4-di(diphenylphosphino)-butane
7688-25-7

1,4-di(diphenylphosphino)-butane

[Pd(N3)(2-(2'-thienyl)pyridine)]2(μ-1,4-bis(diphenylphosphino)butane)
1190630-94-4

[Pd(N3)(2-(2'-thienyl)pyridine)]2(μ-1,4-bis(diphenylphosphino)butane)

Conditions
ConditionsYield
In dichloromethane (under N2 or Ar, Schlenk); CH2Cl2 soln. of ligand added to soln. of Pd-complex in CH2Cl2, stirred for 5 h; solvent removed, washed with Et2O, recrystd. from CH2Cl2-n-hexane; elem.anal.;96%

7688-25-7Relevant articles and documents

Catalytic Cleavage of Unactivated C(aryl)-P Bonds by Chromium

Ling, Liang,Luo, Meiming,Tang, Jinghua,Yuan, Shuqing,Zeng, Xiaoming

, p. 1581 - 1586 (2022/03/14)

We describe here the coupling to transform aryl phosphine derivatives by the cleavage of unactivated C(aryl)-P bonds with chromium catalysis, allowing us to achieve the reaction with alkyl bromides and arylmagnesium reagents under mild conditions. Mechani

Method for preparing aryl ketone derivatives

-

Paragraph 0019, (2019/10/01)

The present invention discloses a method for preparing aryl ketone derivatives. The method provided by the invention adopts 1-(hetero)arylcycloalcohol as a starting material, and raw materials are easy to obtain and have a plurality of kinds; the products obtained by utilizing the method have various types and wide applications, and the obtained products can be conveniently converted and derivatized to obtain important phosphorus ligands and catalysts; and in addition, the method disclosed in the invention has the advantages of mild reaction conditions, a high yield of the target products, lowpollution and a simple reaction operation and post-treatment process, and is suitable for industrial production.

Bisphosphine catalyzed sequential [3 + 2] cycloaddition and Michael addition of ynones with benzylidenepyrazolones: Via dual α′,α′-C(sp3)-H bifunctionalization to construct cyclopentanone-fused spiro-pyrazolones

Zhang, Jiayong,Miao, Zhiwei

supporting information, p. 9461 - 9471 (2019/01/03)

A bisphosphine-catalyzed sequential [3 + 2] cycloaddition and Michael addition reaction of ynones with benzylidenepyrazolones has been developed. Under the catalysis of DPPB [1,4-bis(diphenylphosphino)butane], the reaction proceeded smoothly to give spiro-[cyclopentanone] pyrazolone derivatives in moderate to good yields with good diastereoselectivities via sequential dual α′,α′-C(sp3)-H bifunctionalization annulation. This strategy provides a novel route toward the synthesis of spiro-[cyclopentanone] pyrazolones containing three contiguous stereocenters which possess potential pharmaceutical activities.

Synthesis of pincer ruthenium RuCl(CNN)(PP) catalysts from [RuCl(μ-Cl)(η6-p-cymene)]2

Zhang, Shuanming,Baratta, Walter

supporting information, p. 3339 - 3342 (2013/07/19)

The cationic [RuCl(η6-p-cymene)(HCNNa)]Cl (1a) (HCNNa = 1-(6-arylpyridin-2-yl)methanamine) and the neutral RuCl 2(η6-p-cymene)(HCNNb) (1b) (HCNN b = 2-aminomethylbenzo[h]quinoline) complexes have been obtained by reaction of the precursor [RuCl(μ-Cl)(η6-p-cymene)] 2 with the corresponding nitrogen ligand (HCNNa and HCNNb) in THF. Complex 1a reacts cleanly with monodentate (P = PPh3) and bidentate phosphines (PP = dppb, dppf) in ethanol in the presence of NEt3, affording the pincer catalysts RuCl(CNN a)(PPh3)2 (2) and RuCl(CNNa)(PP) (PP = dppb 3, dppf 4). Similarly, the benzo[h]quinoline pincer derivative RuCl(CNNb)(dppb) (5) is obtained from 1b and dppb. Complex 3 has also been prepared in a one-pot reaction from [RuCl(μ-Cl)(η6-p- cymene)]2, HCNNa, and dppb in ethanol. Similarly, the chiral complex RuCl(CNNa)((R,S)-Josiphos) was isolated as a single stereoisomer by treatment of [RuCl(μ-Cl)(η6-p-cymene)] 2 with HCNNa and (R,S)-Josiphos in 1-butanol. Reaction of 1a and 1b with dppb affords cymene diphosphine species by displacement of the HCCN ligand.

A catalytic method for the reduction of secondary and tertiary phosphine oxides

Berthod, Mika?l,Favre-Réguillon, Alain,Mohamad, Jahjah,Mignani, Gérard,Docherty, Gordon,Lemaire, Marc

, p. 1545 - 1548 (2008/02/05)

TMDS has been found to be an efficient hydride source for the reduction of tertiary and secondary phosphine oxides using a catalytic amount of Ti(Oi-Pr)4. All classes of tertiary phosphine oxides, such as triaryl, trialkyl, and diphosphine, were effectively reduced. Georg Thieme Verlag Stuttgart.

A mild and efficient CsOH-promoted synthesis of ditertiary phosphines

Honaker, Matthew T.,Salvatore, Ralph Nicholas

, p. 277 - 283 (2007/10/03)

A mild and efficient method for the synthesis of ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, various dihalides were coupled with diphenylphosphine at room temperature, and the results have demonstrated that this methodology offers a general synthetic procedure producing a variety of ditertiary phosphines in high yields.

CsOH-promoted P-alkylation: A convenient and highly efficient synthesis of tertiary phosphines

Honaker, Matthew T.,Sandefur, Benjamin J.,Hargett, James L.,McDaniel, Alicia L.,Salvatore, Ralph Nicholas

, p. 8373 - 7377 (2007/10/03)

A mild and efficient method for the synthesis of tertiary phosphines and ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves and DMF at room temperature, various secondary phosphines and alkyl bromides were examined, and the results have demonstrated that this methodology offers a general synthetic procedure to produce tertiary phosphines in moderate to high yields. Optically active tertiary phosphine synthesis is also described.

Preparation of organohalosilanes

-

, (2008/06/13)

When oganohalosilanes are prepared by charging a reactor with a contact mass containing a metallic silicon powder and a copper catalyst, and introducing an organohalide-containing gas into the reactor to effect the direct reaction, a poly(organo)phosphino compound is added to the contact mass. The invention is successful in producing organohalosilanes at a significantly improved production rate without reducing the selectivity of useful silane.

Method for producing benzoic acid derivatives

-

, (2008/06/13)

The invention relates to a method for producing a benzoic acid derivative represented by the general formula (1). The method includes the step of reacting an aromatic compound represented by the general formula (2), with carbon monoxide and a hydroxy compound (i.e., water or an alcohol), in the presence of (a) a metal compound containing a metal of 8, 9 and 10 groups of periodic table, (b) a first phosphine derivative represented by the general formula (R1)2P—Q—P(R1)2, and (c) a base, It is possible to easily and efficiently produce the benzoic acid derivative by the method.

Process for the hydrogenation of imines

-

, (2008/06/13)

A process for the hydrogenation of imines with hydrogen under elevated pressure in the presence of iridium catalysts containing diphosphine ligands, with or without an inert solvent, the reaction mixture containing a soluble ammonium chloride, bromide or iodide or a soluble metal chloride, bromide, or iodide, wherein the reaction mixture additionally contains at least one solid acid with the exception of ion exchangers. Improved optical yields and high chemical conversion rates are achieved while the catalyst is easily separable.

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