Skip to Content
Merck
All Photos(1)

Documents

349720

Sigma-Aldrich

(3-Carboxypropyl)triphenylphosphonium bromide

98%

Synonym(s):

(4-Hydroxy-4-oxobutyl)triphenylphosphonium bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
HO2C(CH2)3P(C6H5)3Br
CAS Number:
17857-14-6
Molecular Weight:
429.29
MDL number:
MFCD00274196
UNSPSC Code:
12352002
PubChem Substance ID:
24861704
NACRES:
NA.22

Assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

244-247 °C (lit.)

SMILES string

[Br-].OC(=O)CCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C22H21O2P.BrH/c23-22(24)17-10-18-25(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H

InChI key

NKVJKVMGJABKHV-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • Piperamide analogs as histone deacetylase (HDAC) inhibitors with antitumor activity
  • Boron-containing benzoxaboroles as antimalarial agents
  • Methyl alkenyl quinolones as antimycobacterial agents
  • Solandelactone E via Sharpless epoxidation, Taber cyclopropanation, chemoselective reductions and lithiation-borylation-allylation sequence
  • Organotin compounds as antifungal agents
  • Oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B for negative regulation of insulin pathway (a promising target for treatment of diabetes and obesity)
  • 11-oxa prostaglandin analogs with ocular hypotensive 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Min Han et al.
Molecular pharmaceutics, 11(8), 2640-2649 (2014-05-09)
In this study, doxorubicin (DOX) was conjugated to a lipophilic triphenylphosphonium (TPP) that is selectively taken up by the mitochondrial membrane of cells. This new derivative of DOX, i.e., TPP-DOX, was characterized by infrared spectroscopy (IR), nuclear magnetic resonance ((1)H
Xin-Cheng Zhong et al.
Pharmaceutical development and technology, 26(1), 21-29 (2020-10-20)
Multidrug resistance (MDR) is a serious challenge in chemotherapy and also a major threat to breast cancer treatment. As an intracellular energy factory, mitochondria provide energy for drug efflux and are deeply involved in multidrug resistance. Mitochondrial targeted delivery of
Hongqiao Zhou et al.
Biomaterials science, 6(6), 1535-1545 (2018-04-20)
Although microwave (MW) thermal therapy has been widely studied for the treatment of tumors due to its less invasiveness, recurrence of tumors is still observed because of the relatively low bioavailability of MW sensitizers. For enhancing the bioavailability of MW

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service