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Sigma-Aldrich

1,3-Bis(diphenylphosphino)propane

97%

Synonym(s):

dppp

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About This Item

Linear Formula:
(C6H5)2PCH2CH2CH2P(C6H5)2
CAS Number:
6737-42-4
Molecular Weight:
412.44
Beilstein:
2821785
EC Number:
229-791-2
MDL number:
MFCD00003050
UNSPSC Code:
12352002
PubChem Substance ID:
24855854
NACRES:
NA.22

Quality Level

200

Assay

97%

form

solid

reaction suitability

reagent type: ligand
reaction type: C-C Bond Formation
reagent type: ligand
reaction type: Carbonylations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

63-65 °C (lit.)

functional group

phosphine

SMILES string

C(CP(c1ccccc1)c2ccccc2)CP(c3ccccc3)c4ccccc4

InChI

1S/C27H26P2/c1-5-14-24(15-6-1)28(25-16-7-2-8-17-25)22-13-23-29(26-18-9-3-10-19-26)27-20-11-4-12-21-27/h1-12,14-21H,13,22-23H2

InChI key

LVEYOSJUKRVCCF-UHFFFAOYSA-N

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General description

1,3-Bis(diphenylphosphino)propane is an organophosphorus compound, that belongs to the class of diphosphine ligands. It is used in transition metal-catalyzed cross-coupling reactions such as Suzuki-Miyaura coupling, Sonogashira coupling, and Negishi coupling reactions. 1,3-Bis(diphenylphosphino)propane is also used in the development of biologically active metal coordination complexes because of its ability to coordinate well with the metals via monodentate or bidentate manner.

Application

  • Nanoclusterzyme Dual Colorimetric Sensings: The study explored the utility of 1,3-Bis(diphenylphosphino)propane in creating nanoclusterzymes, demonstrating applications in dual colorimetric sensings. This application suggests significant potential in analytical chemistry and sensor development (Zhao et al., 2023).
  • Assembly of Icosahedral Units: Research detailed the use of 1,3-Bis(diphenylphosphino)propane in the stronger assembly of icosahedral units within metal clusters, emphasizing its role in enhancing structural stability and potential applications in nanotechnology (Zhou et al., 2023).
  • Synthesis and Stability of Gold Clusters: A publication highlighted the synthesis and evaluation of the stability of mixed-diphosphine ligated gold clusters using 1,3-Bis(diphenylphosphino)propane, underlining its critical role in organometallic chemistry and potential industrial applications (Philliber et al., 2022).
  • Size-Conversion in Gold Phosphine Clusters: The work investigated core charge density effects on size-conversion from Au(6) P(8) to Au(8) P(8) Cl(2), facilitated by 1,3-Bis(diphenylphosphino)propane, presenting new insights into cluster chemistry and its implications for catalytic and electronic applications (Lv et al., 2020).
  • Synthesis of Donor-Acceptor Diblock Copolymer: This study employed 1,3-Bis(diphenylphosphino)propane in sequential polymerizations to synthesize a novel donor-acceptor diblock copolymer, showcasing the versatility of this ligand in polymer chemistry and its potential for creating advanced materials (Ono et al., 2014).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Zelinda Engelbrecht et al.
Anti-cancer agents in medicinal chemistry, 18(3), 394-400 (2017-05-23)
A broad range of metal-coordinated complexes have been studied for their anticancer activities. However, some of these complexes display high toxicity profiles to non-malignant cells, therefore limiting their use in cancer therapeutics. Several silver(I) triphenylphosphine adducts were prepared as 1:1
Nathália Cristina Campanella et al.
Genetics and molecular biology, 35(1), 159-163 (2012-04-07)
The antitumorigenic potential of two palladium(II) complexes, [Pd(ca(2)-o-phen)Cl(2)] - C1 and [Pd(dmba)(dppp)Cl] - C2, was evaluated, using MDA-MB-435 cells, a human breast adenocarcinoma cell-line that does not express the estrogen receptor α (ER-). Growth inhibition and induced alterations in cell-morphology
Wanessa Carvalho Pires et al.
Molecular and cellular biochemistry, 438(1-2), 199-217 (2017-08-11)
The aim of this work was the synthesis, characterization, and cytotoxicity evaluation of three new Ru(II) complexes with a general formula [Ru(Spy)(bipy)(P-P)]PF
Renxuan Xie et al.
Nature communications, 11(1), 893-893 (2020-02-16)
The glass transition temperature (Tg) is a key property that dictates the applicability of conjugated polymers. The Tg demarks the transition into a brittle glassy state, making its accurate prediction for conjugated polymers crucial for the design of soft, stretchable
Heyan Jiang et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(34), 8280-8285 (2017-03-24)
The effect of chain structure on flexibility and stability of macromolecules containing weak P-Fe metal coordination bonds is studied. Migration insertion polymerization (MIP) of FpC
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