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B102806

Sigma-Aldrich

Butyltriphenylphosphonium bromide

99%

Synonym(s):

NSC 59684, TBP

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About This Item

Linear Formula:
(C6H5)3P(Br)CH2CH2CH2CH3
CAS Number:
1779-51-7
Molecular Weight:
399.30
Beilstein/REAXYS Number:
3580224
EC Number:
217-219-4
MDL number:
MFCD00011855
UNSPSC Code:
12352002
PubChem Substance ID:
24891546
NACRES:
NA.22

assay

99%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

240-243 °C (lit.)

SMILES string

[Br-].CCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C22H24P.BrH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1

InChI key

IKWKJIWDLVYZIY-UHFFFAOYSA-M

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Application

Reactant for:
  • Free radical 5-exo-dig cyclization
  • Intramolecular hydroacylalkoxylation
  • Wittig reactions for stereoselective synthesis of alkenes
  • Dimerization of α-olefins
  • Alkylidenation of hydrazides for synthesis of indoles
  • Tandem cyclization and 1,2-thiolate shift of nitrogen ylides

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCJ1143
MKBX5378V
MKBL6767V
MKBL6765V
MKBH4711V

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C W Keevil et al.
Analytical biochemistry, 139(1), 228-236 (1984-05-15)
Polyvinyl chloride membrane electrodes sensitive to tetraphenyl phosphonium (TPP+), butyltriphenyl phosphonium ( bTPP +), and methyltriphenyl phosphonium ( mTPP +) ions have been compared for the determination of the electrical potential difference (delta psi) of the oral bacteria, Streptococcus mutans
A P Singh et al.
Archives of biochemistry and biophysics, 245(2), 436-445 (1986-03-01)
Equilibration of the butyltriphenyl phosphonium (BTPP+) cation into cytochrome c oxidase reconstituted proteoliposomes was measured potentiometrically. The maximum membrane potential (delta psi) generated by oxidase activity was estimated to lie between -65 and -90 mV, vesicle interior negative, when internal
Jing Wang et al.
Journal of the American Society for Mass Spectrometry, 22(10), 1771-1783 (2011-09-29)
Fixed charge chemical modifications on peptides and proteins can impact fragmentation behaviors in tandem mass spectrometry (MS/MS). In this study, we employed a thiol-specific cationic alkylation reagent, (4-iodobutyl)triphenylphosphonium (IBTP), to selectively modify cysteine thiol groups in mitochondrial proteome samples. Tandem
J E McCarthy et al.
The Biochemical journal, 196(1), 311-321 (1981-04-15)
1. Aerobic respiration by cells of Paracoccus dentrificans drives the uptake of the lipophilic cation butyltriphenylphosphonium. Anaerobiosis or addition of an uncoupler of oxidative phosphorylation (carbonyl cyanide p-trifluoromethoxyphenylhydrazone) results in efflux of the cation. Changes in the concentration of butyltriphenylphosphonium
A J Clark et al.
The Biochemical journal, 200(2), 389-397 (1981-11-15)
1. The membrane potential in intact cells of Rhodopseudomonas capsulata during photosynthesis and during dark respiration has been measured by two independent methods. 2. The light-induced and O2-induced shifts in the carotenoid absorption spectrum were measured in the intact cells.
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