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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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Synlett, 2771-2771 (2006)
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(-)
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
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
D P Nolan et al.
European journal of biochemistry, 267(15), 4615-4623 (2000-07-21)
The plasma-membrane potential (Delta(psi)p) in bloodstream forms of Trypanosoma brucei was studied using several different radiolabelled probes: 86Rb+ and [14C]SCN- were used to report Delta(psi)p directly because they distribute in easily measured quantities across the plasma membrane only, and [3H]methyltriphenylphosphonium
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