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219592

Sigma-Aldrich

2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide

98%

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Empirical Formula (Hill Notation):
C24H26BrO2P
CAS Number:
69891-92-5
Molecular Weight:
457.34
Beilstein:
4117571
EC Number:
274-189-5
MDL number:
MFCD00012000
UNSPSC Code:
12352005
PubChem Substance ID:
24853138

Assay

98%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

193-195 °C (lit.)

SMILES string

[Br-].C1COC(CC[P+](c2ccccc2)(c3ccccc3)c4ccccc4)OC1

InChI

1S/C24H26O2P.BrH/c1-4-11-21(12-5-1)27(22-13-6-2-7-14-22,23-15-8-3-9-16-23)20-17-24-25-18-10-19-26-24;/h1-9,11-16,24H,10,17-20H2;1H/q+1;/p-1

InChI key

XETDBHNHTOJWPZ-UHFFFAOYSA-M

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Application

2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide can be used:
  • As a three-carbon homologating agent used to prepare α,β- or β,γ- unsaturated compounds.
  • In the olefination of methyl 5-oxopentanoate to yield methyl 7-(1,3-dioxan2-yl)hept-(5Z)-enoate.
  • As a cathode interfacial layer material in polymer solar cells.

Reactant for:
  • Wittig olefination

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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2-(1, 3-Dioxan-2-yl)-ethylidenetriphenylphosphorane, A New Three-Carbon Homologating Agent
Stowell JC and Keith DR
Synthesis, 1979(2), 32-133 (1979)
Algal pheromone biosynthesis: stereochemical analysis and mechanistic implications in gametes of Ectocarpus siliculosus
Rui F and Boland W
The Journal of Organic Chemistry, 75(12), 3958-3964 (2010)
Organophosphorus Derivatives as Cathode Interfacial-Layer Materials for Highly Efficient Fullerene-Free Polymer Solar Cells
Gupta M, et al.
ACS Applied Materials & Interfaces, 10(42), 35896-35903 (2018)

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