Dodecyltriphenylphosphonium bromide

Base Information

• Chemical Name: Dodecyltriphenylphosphonium bromide
• CAS No.: 15510-55-1
• Molecular Formula: C30H40 P . Br
• Molecular Weight: 511.525
• Hs Code.: 2931900090
• European Community (EC) Number: 239-538-8
• UNII: 2OQV5UAF87
• DSSTox Substance ID: DTXSID90935130
• Wikidata: Q27156154
• ChEMBL ID: CHEMBL3229257
• Mol file: 15510-55-1.mol

Synonyms:dodecyltriphenylphosphonium;dodecyltriphenylphosphonium bromide

Chemical Property of Dodecyltriphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: WHITE TO YELLOW POWDER
• Melting Point: 85-88 ºC(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 13.59000
• Density: g/cm³
• LogP: 4.90540
• Storage Temp.: RT
• Sensitive.: Hygroscopic
• Solubility.: Soluble in DMSO (50 mg/ml) or ethanol (25 mg/mL)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 510.20510
• Heavy Atom Count: 32
• Complexity: 380

Purity/Quality:

98%, ^*data from raw suppliers

Dodecyltriphenylphosphonium bromide 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Description: Dodecyl-TPP (15510-55-1) is a mitochondria-targeting agent which inhibits mitochondrial function inhibiting oxidative phosphorylation and shifting cell metabolism to glycolysis.1 Potently eradicates cancer stem cells (50 nm to 1 mM) selectively over normal cells1. Synergizes with FDA-approved drugs such as doxycycline and niclosamide as well as natural compounds such as berberine. Selectively inhibits the growth of Gram-positive over Gram-negative bacteria.2

Technology Process of Dodecyltriphenylphosphonium bromide

There total 3 articles about Dodecyltriphenylphosphonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-dodecylbromide (143-15-7) + triphenylphosphine (603-35-0) → dodecyltriphenylphosphonium bromide (15510-55-1)

Guidance literature:

In toluene; Reflux;

DOI:10.1021/jf302872a

Reference yield:

bromoundecane (693-67-4) + triphenylphosphine (603-35-0) → dodecyltriphenylphosphonium bromide (15510-55-1)

Guidance literature:

In benzene; Heating;

Reference yield:

→ dodecyltriphenylphosphonium bromide (15510-55-1)

Guidance literature:

DOI:10.1016/0009-3084(71)90053-3

upstream raw materials:

1-dodecylbromide

triphenylphosphine

bromoundecane

Downstream raw materials:

C₃₀H₄₀P⁽¹⁺⁾*C₂H₆O₂PS₂^(1-)

dodecylidenetriphenylphosphorane

2,3-dihydro-1-benzoxepin-4-carboxylic acid ethylester

Refernces

• 1、 Luká?, Milo?,Pisár?ik, Martin,Garajová, Mária,Mrva, Martin,Du?eková, Aneta,Vrták, Andrej,Horáková, Renáta,Horváth, Branislav,Devínsky, Ferdinand. "Synthesis, Surface Activity, and Biological Activities of Phosphonium and Metronidazole Salts". . p. 1025 - 1032. Retrieved 2020/07/27.
• 2、 Vidal, Diogo M.,Fávaro, Carla F.,Guimar?es, Matheus M.,Zarbin, Paulo H. G.. "Identification and synthesis of the male-produced sex pheromone of the soldier beetle chauliognathus fallax (Coleoptera: Cantharidae)". . p. 1506 - 1511. Retrieved 2016/08/10.