|
|
| | 1,4-Bis(diphenylphosphino)butane Basic information |
| | 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) |
| | 1,4-Bis(diphenylphosphino)butane Usage And Synthesis |
| Chemical Properties | 1,4-Bis(diphenylphosphino)butane is a white solid that is soluble in organic solvents.
| | 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. | | reaction suitability | reagent type: ligand
reaction type: Alkylations
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Isomerizations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling | | 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 | Ethanol-->Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->Sodium-->Magnesium sulfate-->Acetone-->n-Butyllithium-->Triphenylphosphine-->Lithium-->Diphenylphosphine-->1,4-Dibromobutane-->1,4-Dichlorobutane-->Diphenyl[4-(diphenylphosphinyl)butyl]phosphine oxide | | 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-->(4-chlorobutyl)diphenylphosphane-->Tetraphenylbiphosphine |
|