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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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

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