Pentane-1,5-diylbis(triphenylphosphonium) bromide

Name: Pentane-1,5-diylbis(triphenylphosphonium) bromide
Brand: ChemScene
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CAS No. 22884-31-7
Cat. No. CS-0312019
Purity≥98%
MDL No.MFCD00051887

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Pentane-1,5-diylbis(triphenylphosphonium) bromide|CS-0312019

Structure of 22884-31-7

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General Information

CAS No. 22884-31-7
Cat. No. CS-0312019
Purity ≥98%
MDL No. MFCD00051887
Storage 4°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₁H₄₀Br₂P₂
Molecular Weight 754.51
Synonym(s) triphenyl(5-triphenylphosphaniumylpentyl)phosphanium,dibromide
SMILES C1([P+](CCCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)=CC=CC=C1.[Br-].[Br-]

Description

Pentane-1,5-diylbis(triphenylphosphonium) bromide features two triphenylphosphonium groups linked by a flexible pentane chain, enabling efficient phase-transfer catalysis. This bifunctional cationic reagent facilitates the transfer of anions across immiscible phases, enhancing reaction rates in organic synthesis. Its stability under standard conditions supports reliable performance in multistep transformations.

Application

Pentane-1,5-diylbis(triphenylphosphonium) bromide serves as a versatile diquaternary phosphonium salt enabling efficient Wittig-type olefination and Horner–Wadsworth–Emmons reactions. Its linear aliphatic spacer provides enhanced solubility and reduced steric crowding compared to symmetric analogs, facilitating high-yielding transformations with aldehydes and ketones. The product exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for scalable synthesis of conjugated dienes and functionalized olefins in medicinal chemistry and materials science applications.

Synthesis

Route1
- 111-24-0
- 603-35-0
- ~64%
- In-stock
  
  22884-31-7
References
- Calcagno, Patrizia; Kariuki, Benson M.; Kitchin, Simon J.; Robinson, James M. A.; Philp, Douglas; Harris, Kenneth D. M. Chemistry - A European Journal, 2000 , vol. 6, # 13 p. 2338 - 2349

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 0
LogP 2.1529
H_Acceptors 0
H_Donors 0
Rotatable_Bonds 12

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Pentane-1,5-diylbis(triphenylphosphonium) bromide

CAS No. 22884-31-7

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