[3-(Dimethylamino)propyl]triphenylphosphonium bromide hydrobromide Chemical Properties

Melting point:

283-285 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Off-White

Stability:

Hygroscopic

InChI

InChI=1S/C23H27NP.2BrH/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;2*1H/q+1;;/p-1

InChIKey

NEQVFHFOWYYPBS-UHFFFAOYSA-M

SMILES

[P+](C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)CCCN(C)C.[Br-].Br

CAS DataBase Reference

27710-82-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10

MSDS

• Language:English Provider:SigmaAldrich

[3-(Dimethylamino)propyl]triphenylphosphonium bromide hydrobromide Usage And Synthesis

Uses

(3-(Dimethylamino)propyl)triphenylphosphonium bromide is used as a reactant for preparing chlorpheniramine analogs reverse chloroquine resistance in Plasmodium falciparum by inhibiting PfCRT.

Synthesis

To a suspension of (3-bromopropyl)triphenylphosphonium bromide (1.0 g, 2.1 mmol) in ethanol (5 mL) was slowly added 40% aqueous dimethylamine (3 mL) at room temperature. The reaction mixture was transferred to a sealed microwave reaction tube and heated at 100 °C with stirring for 30 min. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by recrystallization in acetonitrile to afford [3-(dimethylamino)propyl]triphenylphosphonium bromide hydrobromide (0.90 g, 82% yield) as a white solid, which was used directly in the subsequent reaction.ESI MS m/z 348.3 (corresponding to Ph3PCH2CH2CH2CH2NMe2+ ions).

References

[1] Patent: WO2012/79017, 2012, A1. Location in patent: Page/Page column 68
[2] Patent: US2007/232814, 2007, A1. Location in patent: Page/Page column 24

[3-(Dimethylamino)propyl]triphenylphosphonium bromide hydrobromide(27710-82-3)Related Product Information

• Scopolamine hydrobromide
• Sodium bromate
• Clidinium bromide
• Hydrogen bromide
• Propyl gallate
• (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
• Propyl butyrate
• HYOSCINE N BUTYL BROMIDE BP
• Ethidium bromide
• DEXTROMETHORPHAN HYDROBROMIDE
• Methyl bromide
• Olopatadine
• 3-((Dimethylamino)propyl)triphenylphosphonium bromide
• (3-AMINOPROPYL)DIPHENYLPHOSPHINE
• [3-(Dimethylamino)propyl]triphenylphosphonium bromide hydrobromide
• Bromide