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440418

Sigma-Aldrich

1,3-Bis(dicyclohexylphosphino)propane

95%

Synonym(s):

1,3-Bis(dicyclohexylphosphanyl)propane

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About This Item

Linear Formula:
(C6H11)2P(CH2)3P(C6H11)2
CAS Number:
Molecular Weight:
436.63
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

form

viscous liquid

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

refractive index

n20/D 1.554 (lit.)

bp

>350 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

C1CCC(CC1)P(CCCP(C2CCCCC2)C3CCCCC3)C4CCCCC4

InChI

1S/C27H50P2/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/h24-27H,1-23H2

InChI key

RSJBEKXKEUQLER-UHFFFAOYSA-N

General description

1,3-Bis(dicyclohexylphosphino)propane is a versatile compound that serves as a ligand in organometallic chemistry.

Application

1,3-Bis(dicyclohexylphosphino)propane is used as a ligand in the:
  • Synthesis of gold clusters.
  • Palladium-catalyzed decarboxylative coupling reaction.

Features and Benefits

The bulky nature of 1,3-Bis(dicyclohexylphosphino)propane provides steric hindrance to prevent unwanted side reactions, leading to higher yields and selectivity.

Storage Class Code

10 - Combustible liquids

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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Transition-metal-catalyzed C--H alkylation using alkenes
Dong Z, et al.
Chemical Reviews, 117(13), 9333-9403 (2017)
Synthesis and Characterization of Gold Clusters Ligated with 1, 3-Bis (dicyclohexylphosphino) propane
Johnson GE, et al.
ChemPlusChem, 78(9), 1033-1039 (2013)
New strategies for the transition-metal catalyzed synthesis of aliphatic amines
Trowbridge A, et al.
Chemical Reviews, 120(5), 2613-2692 (2020)

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