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377538

Sigma-Aldrich

Heptyltriphenylphosphonium bromide

97%

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About This Item

Linear Formula:
CH3(CH2)6P(C6H5)3Br
CAS Number:
13423-48-8
Molecular Weight:
441.38
EC Number:
236-539-5
MDL number:
MFCD00050249
UNSPSC Code:
12352002
PubChem Substance ID:
24863510
NACRES:
NA.22

Quality Level

100

Assay

97%

reaction suitability

reaction type: C-C Bond Formation

mp

173-176 °C (lit.)

SMILES string

[Br-].CCCCCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C25H30P.BrH/c1-2-3-4-5-15-22-26(23-16-9-6-10-17-23,24-18-11-7-12-19-24)25-20-13-8-14-21-25;/h6-14,16-21H,2-5,15,22H2,1H3;1H/q+1;/p-1

InChI key

WCZSOHSGMBVYFW-UHFFFAOYSA-M

Application

Reactant for:
  • Stereospecific rearrangement of epoxides to quaternary carbaldehydes
  • Synthesis of the male pheromone of two species of termite Zootermopsis
  • Regio- and stereoselective TEMPO oxidation
  • Diastereoselective synthesis of climacostol for antitumor activity
  • Enantioselective synthesis of chiral vinylphosphonate and phosphonate analogs of immunosuppressive agent FTY720
  • Preparation of embelin derivatives with XIAP inhibitory and anticancer activity

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

Storage Class Code

11 - Combustible Solids

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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Darya A Kuznetsova et al.
Journal of materials chemistry. B, 7(46), 7351-7362 (2019-11-07)
The purpose of this work was to obtain cationic liposomes based on 1,2-dipalmitoyl-sn-glycero-3-phosphocholine noncovalently modified using alkyltriphenylphosphonium bromides (TPPB-n) with different lengths of hydrocarbon tail for targeted delivery to mitochondria. The hydrodynamic diameter and electrokinetic potential of hybrid liposomes depending
Tejia Zhang et al.
Journal of lipid research, 56(8), 1501-1510 (2015-06-11)
Apoptosis is an intricately regulated cellular process that proceeds through different cell type- and signal-dependent pathways. In the mitochondrial apoptotic program, mitochondrial outer membrane permeabilization by BCL-2 proteins leads to the release of apoptogenic factors, caspase activation, and cell death.

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