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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)

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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Fengling Cui et al.
Journal of pharmaceutical and biomedical analysis, 43(3), 1033-1038 (2006-12-23)
A method for the determination of bismuth in pharmaceutical products using methyltriphenylphosphonium bromide as a molecular probe based on the resonance light scattering (RLS) technique was developed. In the presence of Tween-20, bismuth reacts with a large excess of I(-)
Synlett, 2771-2771 (2006)
Abhijit Mukhopadhyay et al.
Advanced drug delivery reviews, 59(8), 729-738 (2007-07-31)
Mitochondria is where the bulk of the cell's ATP is produced. Mutations occur to genes coding for members of the complexes involved in energy production. Some are a result of damages to nuclear coded genes and others to mitochondrial coded
Brian D Fink et al.
The Journal of pharmacology and experimental therapeutics, 342(3), 709-719 (2012-06-05)
Mitochondrial-targeted analogs of coenzyme Q (CoQ) are under development to reduce oxidative damage induced by a variety of disease states. However, there is a need to understand the bioenergetic effects of these agents and whether or not these effects are
E T Polymeropoulos et al.
Proceedings. Biological sciences, 279(1726), 185-193 (2011-06-03)
Metabolic rates of mammals presumably increased during the evolution of endothermy, but molecular and cellular mechanisms underlying basal metabolic rate (BMR) are still not understood. It has been established that mitochondrial basal proton leak contributes significantly to BMR. Comparative studies
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