(4-carboxybutyl)triphenylphosphanium bromide

• ChemBase ID: 74853
• Molecular Formular: C23H24BrO2P
• Molecular Mass: 443.313221
• Monoisotopic Mass: 442.06972864
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CCCCC(=O)O.[Br-]
• Canonical SMILES: OC(=O)CCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: 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
• InChIKey: MLOSJPZSZWUDSK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-carboxybutyl)triphenylphosphanium bromide
• IUPAC Traditional name: (4-carboxybutyl)triphenylphosphanium bromide
• Synonyms: (4-Carboxybutyl)triphenylphosphonium bromide; (4-Carboxybutyl)triphenyl-phosphonium Bromide; Triphenyl(4-carboxybutyl)phosphonium Bromide; 5-(Triphenylphosphonio)pentanoic acid bromide; Carboxybutyltriphenylphosphonium bromide; NSC 147756; (4-Carboxybutyl)triphenylphosphonium bromide; (4-羧丁基)三苯基溴化磷鎓; (4-羧丁基)三苯基溴化膦

Database IDs

• CAS Number: 17814-85-6
• EC Number: 241-782-5
• MDL Number: MFCD00011906
• Beilstein Number: 3586477
• PubChem SID: 24849711; 162039771
• PubChem CID: 161236

CALCULATED PROPERTIES

• Acid pKa: 3.8977032
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4681077
• LogD (pH = 7.4): 1.8612405
• Log P: 5.076017
• Molar Refractivity: 107.3612 cm^3
• Polarizability: 42.217678 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 198-200°C; 204-207 °C(lit.); 205-209°C
• Flash Point: 195°C(383°F)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Hygroscopic; Irritant/Hygroscopic
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-36; 36
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: (C6H5)3P(Br)(CH2)4COOH

DETAILS

Sigma Aldrich - 157945

Packaging
10, 50, 250 g in poly bottle
Application

• Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells1Reactant for preparation of:
• Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions2
• Methyl alkenyl quinolones as antimycobacterial agents3
• Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement4
• Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents5
• Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity6
• Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction7

REFERENCES

• Use of LiHMDS as base in the Wittig reaction with aromatic aldehydes gives a much higher proportion of the trans-alkene than alternative bases such as dimsyl sodium or KO-t-Bu: Tetrahedron Lett., 22, 4185 (1981). See Appendix 1.