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130079

Sigma-Aldrich

Methyltriphenylphosphonium bromide

98%

Synonym(s):

TPMP, Triphenylmethylphosphonium bromide, triphenylmethylphosphonium bromide

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About This Item

Linear Formula:
CH3P(C6H5)3Br
CAS Number:
1779-49-3
Molecular Weight:
357.22
Beilstein:
3599467
EC Number:
217-218-9
MDL number:
MFCD00011804
UNSPSC Code:
12352002
PubChem Substance ID:
24847941
NACRES:
NA.22

Assay

98%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

230-234 °C (lit.)

SMILES string

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

InChI

1S/C19H18P.BrH/c1-20(17-11-5-2-6-12-17,18-13-7-3-8-14-18)19-15-9-4-10-16-19;/h2-16H,1H3;1H/q+1;/p-1

InChI key

LSEFCHWGJNHZNT-UHFFFAOYSA-M

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Application

Used widely for methylenation via the Wittig reaction
Wittig olefination salt employed recently in a synthesis of an enyne which, via ring closing metathesis, provided a benzazepine ring system.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H411

Precautionary Statements

P273 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

>464.0 °F

Flash Point(C)

> 240 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Meredith F Ross et al.
The Biochemical journal, 400(1), 199-208 (2006-09-05)
Lipophilic monocations can pass through phospholipid bilayers and accumulate in negatively-charged compartments such as the mitochondrial matrix, driven by the membrane potential. This property is used to visualize mitochondria, to deliver therapeutic molecules to mitochondria and to measure the membrane
M P Murphy
Expert opinion on biological therapy, 1(5), 753-764 (2001-12-01)
Mitochondrial dysfunction causes or exacerbates a number of diseases. These include genetic disorders such as Friedreich's ataxia where the primary lesion is a defect in a nuclear gene and those diseases caused by mutations to mitochondrial DNA. Mitochondrial damage also
V Borutaite et al.
Biochimica et biophysica acta, 1272(3), 154-158 (1995-12-12)
We investigated the effects of ischemia on the kinetics and control of mitochondria isolated from normal and ischemic heart. The dependence of the respiratory chain, phosphorylation system and proton leak on the mitochondrial membrane potential were measured in mitochondria from
I Madar et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 40(7), 1180-1185 (1999-07-15)
In vitro studies have demonstrated the membrane potential-dependent enhanced uptake of phosphonium salts, including [3H]triphenylmethylphosphonium (TPMP), into mitochondria of carcinoma and glioma-derived tumor cells, suggesting the potential use of phosphonium salts as tracers for tumor imaging. This study characterizes the
Meredith F Ross et al.
The Biochemical journal, 411(3), 633-645 (2008-02-26)
Mitochondria-targeted molecules comprising the lipophilic TPP (triphenylphosphonium) cation covalently linked to a hydrophobic bioactive moiety are used to modify and probe mitochondria in cells and in vivo. However, it is unclear how hydrophobicity affects the rate and extent of their
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