| Identification | More | [Name]
(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide | [CAS]
52509-14-5 | [Synonyms]
(1,3-DIOXOLAN-2-YLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
(1,3-DIOXOLANE-2-YL METHYL) TRIPHENYL PHOSPHONIUM BROMIDE
LABOTEST-BB LT00233112
TRIPHENYL-1,3-DIOXOLAN-2-YLMETHYL-PHOSPHONIUM BROMIDE
2-(1,3)-DIOXOLANE-2-YL-METHYLTRIPHENYLPHOSPHONIUM BROMIDE
Phosphonium, (1,3-dioxolan-2-ylmethyl)triphenyl-, bromide
(1,3-DIOXOLAN-2-YLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE 98%
(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide, 98 %
1,3-Dioxolan-2-ylmethyl-triphenylphosphanium bromide
Triphenyl(1,3-dioxolane-2-ylmethyl)phosphonium·bromide | [EINECS(EC#)]
257-977-3 | [Molecular Formula]
C22H22BrO2P | [MDL Number]
MFCD00011966 | [Molecular Weight]
429.29 | [MOL File]
52509-14-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light brown granular powder | [Melting point ]
193-195 °C(lit.)
| [storage temp. ]
Store below +30°C. | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder or Crystals | [color ]
White to light brown | [Water Solubility ]
Soluble in water (20°C). | [Sensitive ]
Hygroscopic | [InChI]
InChI=1S/C22H22O2P.BrH/c1-4-10-19(11-5-1)25(18-22-23-16-17-24-22,20-12-6-2-7-13-20)21-14-8-3-9-15-21;/h1-15,22H,16-18H2;1H/q+1;/p-1 | [InChIKey]
FRHRVQQUICVJDG-UHFFFAOYSA-M | [SMILES]
[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)CC1OCCO1.[Br-] | [CAS DataBase Reference]
52509-14-5(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light brown granular powder | [Uses]
(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium Bromide is used as a reactant in the synthesis of ketolides methyloxoerythromycins with antibacterial activity as highly potent against macrolide-resistant and susceptible respiratory pathogens. | [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
General procedure: 2-Bromomethyl-1,3-dioxolane (60.0 mmol) and triphenylphosphine (60.0 mmol) were dissolved in toluene (50 mL) and heated to reflux for 24 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and the solid product formed was collected by filtration. The solid was washed with ether and subsequently dried under reduced pressure to give ((1,3-dioxolan-2-yl)methyl)triphenylphosphonium bromide. Yield: 3.5 g (54%). Melting point: 194-195°C. | [Purification Methods]
Wash the crystals with Et2O, dry them in a vacuum and recrystallise them from CH2Cl2/dry Et2O to give prisms m 172-174o, which is raised to 191.5-193o on drying at 56o/0.5mm. [Cresp et al. J Chem Soc, Perkin Trans 1 37 1974.] | [References]
[1] Patent: US2009/170790, 2009, A1. Location in patent: Page/Page column 23
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 41, p. 8342 - 8347,6 |
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