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(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

Product Name(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide
CAS52509-14-5
MFC22H22BrO2P
MW429.29
EINECS257-977-3
MOL File52509-14-5.mol

Chemical Properties

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)

Safety Information

Hazard Codes	Xn
Risk Statements	20/21/22-36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	29329970
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide	English
SigmaAldrich	English
ACROS	English

Usage And Synthesis

Chemical Properties

white to light brown granular powder

Uses

Reactant for:

Preparation of a ratiometric fluorescent probe for specific detection of cysteine over homocysteine and glutathione
Microwave-assisted synthesis of KN-93 as inhibitor of calmodulin kinase II
Preparation of fluorinated spirobenzofuran piperidines as s1 receptor ligands
Synthesis and antitumor agents
Regio-selective preparation of indole derivatives via rhodium-catalyzed domino hydroformylation/indolization

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

4360-63-8

603-35-0

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

52509-14-5

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

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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