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1,4-Bis(diphenylphosphino)butane

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1,4-Bis(diphenylphosphino)butane Basic information

Product Name:
1,4-Bis(diphenylphosphino)butane
Synonyms:
  • [4-(Diphenylphosphino)butyl](diphenyl)phosphine
  • TETRAMETHYLENEBIS(DIPHENYLPHOSPHINE)
  • 98% DPPB
  • Tetramethylenebis(diphenylphosphine) DPPB
  • 1,4-Bis(diphenylphosphino)butane, 98% 5GR
  • 1,4-Bis(diphenylphosphiNA)butane
  • 1,4-Bis(diphenylphosphino)buta
  • 1,4-Bis(diphenylphosphino)butane Butane-1,4-diylbis[diphenylphosphine]
CAS:
7688-25-7
MF:
C28H28P2
MW:
426.47
EINECS:
231-698-7
Product Categories:
  • Phosphines
  • Phosphine Ligands
  • Ligand
  • Synthetic Organic Chemistry
  • Achiral Phosphine
  • Aryl Phosphine
  • organophosphine ligand
Mol File:
7688-25-7.mol
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1,4-Bis(diphenylphosphino)butane Chemical Properties

Melting point:
132-136 °C (lit.)
Boiling point:
542.0±33.0 °C(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
Crystalline Powder
color 
White to almost white
Water Solubility 
Soluble in chloroform. Slightly soluble in water
BRN 
706446
InChI
InChI=1S/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
InChIKey
BCJVBDBJSMFBRW-UHFFFAOYSA-N
SMILES
P(CCCCP(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1
CAS DataBase Reference
7688-25-7(CAS DataBase Reference)
NIST Chemistry Reference
1,4-Bis(diphenylphosphino)butane(7688-25-7)
EPA Substance Registry System
Phosphine, 1,4-butanediylbis[diphenyl- (7688-25-7)
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Safety Information

Hazard Codes 
Xi,F
Risk Statements 
36/38-36/37/38-11
Safety Statements 
26-36-37/39-33-16-7/9
WGK Germany 
3
F 
10-23
TSCA 
Yes
HS Code 
29319090

MSDS

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1,4-Bis(diphenylphosphino)butane Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

1,4-Bis(diphenylphosphino)butane is used in Suzuki reaction. It plays an essential role as a ligand in palladium(0)-catalyzed acylcyanation of arylacetylenes and deprotection of allyloxycarbamates. It acts as a ligand for alkylations, isomerization reactions and in organometallic chemistry. Further, it is used in Heck reaction, Negishi coupling and Sonogashira coupling. In addition to this, it is useful in organometallic chemistry.

storage

Readily oxidized in solution to the phosphine oxide and should be handled under N2 or Ar. The compound is air-stable in the solid state.

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.]

1,4-Bis(diphenylphosphino)butane Preparation Products And Raw materials

Raw materials

EtanolSodium hydroxideHydrochloric acidEthyl acetateTetrahydrofuranDichloromethaneSodiumMagnesium sulfateAcetonen-ButyllithiumTriphenylphosphineLitiumDiphenylphosphine1,4-Dibromobutane1,4-Dichlorobutane

Preparation Products

(S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE(R)-7,7'-BIS(DIPHENYLPHOSPHINO)-1,1'-SPIROBIINDANE(R)-(+)-7,7'-BIS(DIPHENYLPHOSPHINO)-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE(S)-7,7'-Bis[di(p-methylphenyl)phosphino]-1,1'-spirobiindane ,97%(R)-(+)-7,7'-BIS[DI(4-METHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE

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