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:
Molecular Weight:
357.22
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
217-218-9
Beilstein/REAXYS Number:
3599467
MDL number:
Assay:
98%
Form:
powder
Quality Level
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
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.
signalword
Danger
hcodes
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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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
Geoffrey F Kelso et al.
Annals of the New York Academy of Sciences, 959, 263-274 (2002-04-27)
Mitochondrial-targeted antioxidants that selectively block mitochondrial oxidative damage and prevent some types of cell death have been developed. These antioxidants are ubiquinone and tocopherol derivatives and are targeted to mitochondria by covalent attachment to a lipophilic triphenylphosphonium cation. Because of
L Calzada et al.
Archives of andrology, 38(2), 151-155 (1997-03-01)
Membrane potential across the plasma membrane (psi) of human sperm was determined by measuring the accumulation of triphenylmethylphosphonium (TPMP+). Washed sperm of fertile or infertile men were suspended, incubated in low-K+ and high-Na+ or high-K+ and low-Na+ medium, and allowed