[3-(dimethylamino)propyl]triphenylphosphanium bromide

• ChemBase ID: 149898
• Molecular Formular: C23H27BrNP
• Molecular Mass: 428.344941
• Monoisotopic Mass: 427.1064485
• SMILES: CN(C)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: CN(CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C.[Br-]
• InChI: InChI=1S/C23H27NP.BrH/c1-24(2)19-12-20-25(21-13-6-3-7-14-21,22-15-8-4-9-16-22)23-17-10-5-11-18-23;/h3-11,13-18H,12,19-20H2,1-2H3;1H/q+1;/p-1
• InChIKey: SSWPSKSQQSJKKF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(dimethylamino)propyl]triphenylphosphanium bromide
• IUPAC Traditional name: [3-(dimethylamino)propyl]triphenylphosphanium bromide
• Synonyms: (3-(Dimethylamino)propyl)triphenylphosphonium bromide; [3-(二甲基氨基)丙基]三苯基溴化磷

Database IDs

• CAS Number: 18355-96-9
• MDL Number: MFCD00012200
• Beilstein Number: 4637548
• PubChem SID: 24858461; 162244060
• PubChem CID: 15982517

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.306689
• LogD (pH = 7.4): 2.5438683
• Log P: 4.706395
• Molar Refractivity: 110.1057 cm^3
• Polarizability: 43.33508 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 193-196 °C

Safety Information

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

Product Information

• Purity: 98%
• Linear Formula: (CH3)2NCH2CH2CH2P(C6H5)3(Br)

DETAILS

Sigma Aldrich - 305855

Packaging
5 g in glass bottle
Application
Reactant for preparation of:
• Topoisomerase I-targeting antitumor agents1
• C15-C21 stereopentad of discodermolide via cleavage of aminoglycosides, double-bond isomerization, and selective hydroxyl group protection2
• Diphenyl amine based sodium channel blockers, effective against hNav1.23
• Reactant for Wittig reaction with benzaldehyde4