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Merck

130079

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
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
24847941
EC Number:
217-218-9
Beilstein/REAXYS Number:
3599467
MDL number:
MFCD00011804
Assay:
98%
Form:
powder

Key Documents

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Quality Level

200

assay

98%

form

powder

reaction suitability

core: phosphonium, reaction type: C-C Bond Formation

mp

230-234 °C (lit.)

functional group

phosphine

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

Related Categories

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

signalword

Danger

hcodes

H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

wgk

WGK 3

flash_point_f

>464.0 °F

flash_point_c

> 240 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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Certificates of Analysis (COA)

Lot/Batch Number
0000522779
0000522779
0000522783
0000522783
BCCP0498

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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
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
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
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
Synlett, 2771-2771 (2006)
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