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

MSDS

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

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide Usage And Synthesis

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.

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

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

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide(52509-14-5)Related Product Information

• Rocuronium bromide
• Diphenylphosphine
• 2-Bromomethyl-1,3-dioxolane
• Ethidium bromide
• Tetrakis(triphenylphosphine)palladium
• Sodium bromate
• Triphenylphosphine
• Methylmagnesium Bromide
• Methyl cyclopentenolone
• DBDCB
• Chlorodiphenylphosphine
• Triphenylphosphine hydrobromide
• METHYLCYCLOPENTADIENE DIMER
• Chlorodimethylphenylsilane
• Sodium bromide
• Allyl bromide
• Bromo-PEG1-t-butyl ester
• Diethyl bromodifluoromethanephosphonate