(3-carboxypropyl)triphenylphosphanium bromide

• ChemBase ID: 74358
• Molecular Formular: C22H22BrO2P
• Molecular Mass: 429.286641
• Monoisotopic Mass: 428.05407857
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CCCC(=O)O.[Br-]
• Canonical SMILES: OC(=O)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C22H21O2P.BrH/c23-22(24)17-10-18-25(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H
• InChIKey: NKVJKVMGJABKHV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-carboxypropyl)triphenylphosphanium bromide
• IUPAC Traditional name: (3-carboxypropyl)triphenylphosphanium bromide
• Synonyms: (4-Hydroxy-4-oxobutyl)triphenylphosphonium bromide; (3-Carboxypropyl)triphenylphosphonium bromide; 3-Carboxypropyltriphenylphosphonium bromide 98+%; 3-Carboxypropyltriphenylphosphonium bromide; (3-丙羧基)三苯基溴化膦; (3-羧丙基)三苯基溴化膦

Database IDs

• CAS Number: 17857-14-6
• EC Number: 000-000-0
• MDL Number: MFCD00274196
• Beilstein Number: 4173599
• PubChem SID: 162039277; 24861704
• PubChem CID: 10717451

CALCULATED PROPERTIES

• Acid pKa: 3.9646883
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.088036
• LogD (pH = 7.4): 1.4524759
• Log P: 4.6314483
• Molar Refractivity: 102.7602 cm^3
• Polarizability: 40.372 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 244-247 °C(lit.); 244-250°C; 247-250°C

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Linear Formula: HO2C(CH2)3P(C6H5)3Br

DETAILS

Sigma Aldrich - 349720

Packaging
25, 100 g in glass bottle
Application
Reactant for preparation of:
• Piperamide analogs as histone deacetylase (HDAC) inhibitors with antitumor activity1
• Boron-containing benzoxaboroles as antimalarial agents2
• Methyl alkenyl quinolones as antimycobacterial agents3
• Solandelactone E via Sharpless epoxidation, Taber cyclopropanation, chemoselective reductions and lithiation-borylation-allylation sequence4
• Organotin compounds as antifungal agents5
• Oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B for negative regulation of insulin pathway (a promising target for treatment of diabetes and obesity)6
• 11-oxa prostaglandin analogs with ocular hypotensive activity7