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157945

Sigma-Aldrich

(4-Carboxybutyl)triphenylphosphonium bromide

98%

Synonym(s):

5-(Triphenylphosphonio)pentanoic acid bromide, Carboxybutyltriphenylphosphonium bromide, NSC 147756

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About This Item

Linear Formula:
(C6H5)3P(Br)(CH2)4COOH
CAS Number:
17814-85-6
Molecular Weight:
443.31
Beilstein:
3586477
EC Number:
241-782-5
MDL number:
MFCD00011906
UNSPSC Code:
12352107
PubChem Substance ID:
24849711
NACRES:
NA.22

Quality Level

200

Assay

98%

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

204-207 °C (lit.)

functional group

carboxylic acid
phosphine

SMILES string

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

InChI

1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H

InChI key

MLOSJPZSZWUDSK-UHFFFAOYSA-N

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Application

  • Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells

Reactant for preparation of:
  • Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions
  • Methyl alkenyl quinolones as antimycobacterial agents
  • Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement
  • Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents
  • Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity
  • Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

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)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBH0658
0000217293
STBH0658
0000184026
0000118461

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Sigma-Aldrich

304131

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