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B102806

Butyltriphenylphosphonium bromide

Name: Butyltriphenylphosphonium bromide
Brand: ALDRICH

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

UNSPSC Code:

12352002

NACRES:

NA.22

PubChem Substance ID:

24891546

EC Number:

217-219-4

Beilstein/REAXYS Number:

3580224

MDL number:

MFCD00011855

Assay:

99%

Form:

powder

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Properties

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

Description

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

GHS07

signalword

Warning

hcodes

H302 + H312

pcodes

P264 - P280 - P301 + P312 - P302 + P352 + P312 - P362 + P364 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Membrane potentials in reconstituted cytochrome c oxidase proteoliposomes determined by butyltriphenyl phosphonium cation distribution.

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

Comparison of polyvinyl chloride membrane electrodes sensitive to alkylphosphonium ions for the determination of the electrical difference (delta psi) of Streptococcus mutans and Lactobacillus casei.

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

Tandem mass spectrometric characterization of thiol peptides modified by the chemoselective cationic sulfhydryl reagent (4-iodobutyl)triphenylphosphonium--effects of a cationic thiol derivatization on peptide fragmentation.

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

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Global Trade Item Number

SKU	GTIN
B102806-100G	04061833541258