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287970

Sigma-Aldrich

trans-1,2-Bis(diphenylphosphino)ethylene

97%

Synonym(s):

(E)-Vinylenebis[diphenylphosphine], trans-1,2-Ethenediylbis(diphenylphosphine), NSC 132587

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About This Item

Linear Formula:
(C6H5)2PCH=CHP(C6H5)2
CAS Number:
983-81-3
Molecular Weight:
396.40
EC Number:
213-570-2
MDL number:
MFCD00063219
UNSPSC Code:
12352002
PubChem Substance ID:
24857303
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

mp

126-130 °C (lit.)

functional group

phosphine

SMILES string

c1ccc(cc1)P(\C=C\P(c2ccccc2)c3ccccc3)c4ccccc4

InChI

1S/C26H22P2/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/h1-22H/b22-21+

InChI key

NCKJIJSEWKIXAT-QURGRASLSA-N

Application

Catalyst for:
  • Coupling of primary and secondary alkyl halides with aryl grignard reagents
  • Homogeneous hydrogenation of Carbon Dioxide mediated by Ruthenium

Reactant for:
  • Preparation of cyclopalladated derivatives of benzylidene
  • Preparation of cyclopalladated complexes containing tridentate thiosemicarbazone ligands as antimalarial agents
  • Catalytic asymetric intramolecular hydroamination of alkynylamines

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
03614PH
01206DH
07712JF
14220JS
10315BU

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Noora Svahn et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(55), 14654-14667 (2018-08-01)
A series of 4-ethynylaniline gold(I) complexes containing monophosphane (1,3,5-triaza-7-phosphaadamantane (pta; 2), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (3), and PR3 , with R=naphthyl (4), phenyl (5), and ethyl (6)) and diphosphane (bis(diphenylphosphino)acetylene (dppa; 7), trans-1,2-bis(diphenylphosphino)ethene (dppet; 8), 1,2-bis(diphenylphosphino)ethane (dppe; 9), and 1,3-bis(diphenylphosphino)propane (dppp; 10)) ligands

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