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130079

Sigma-Aldrich

Methyltriphenylphosphonium bromide

98%

Sinónimos:

TPMP, Triphenylmethylphosphonium bromide, triphenylmethylphosphonium bromide

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About This Item

Fórmula lineal:
CH3P(C6H5)3Br
Número de CAS:
1779-49-3
Peso molecular:
357.22
Beilstein/REAXYS Number:
3599467
EC Number:
217-218-9
MDL number:
MFCD00011804
UNSPSC Code:
12352002
PubChem Substance ID:
24847941
NACRES:
NA.22

Quality Level

200

assay

98%

form

powder

reaction suitability

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

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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

signalword

Danger

hcodes

H301,H411

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class

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

wgk_germany

WGK 3

flash_point_f

>464.0 °F

flash_point_c

> 240 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000375303
0000375302
0000307099
0000307102
0000375302

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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
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
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
Duncan G G McMillan et al.
The Journal of biological chemistry, 282(24), 17395-17404 (2007-04-17)
Analysis of the atp operon from the thermoalkaliphilic Bacillus sp. TA2.A1 and comparison with other atp operons from alkaliphilic bacteria reveals the presence of a conserved lysine residue at position 180 (Bacillus sp. TA2.A1 numbering) within the a subunit 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
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