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(2-Carboxyethyl)triphenylphosphonium bromide

Product Name(2-Carboxyethyl)triphenylphosphonium bromide
CAS51114-94-4
MFC21H20BrO2P
MW415.26
EINECS
MOL File51114-94-4.mol

Chemical Properties

Melting point	186 °C
storage temp.	Inert atmosphere,Room Temperature
form	Powder or Chunks
color	White to slightly yellow
InChI	InChI=1S/C21H19O2P.BrH/c22-21(23)16-17-24(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20;/h1-15H,16-17H2;1H
InChIKey	BVKRDNIULHRLCO-UHFFFAOYSA-N
SMILES	[P+](CCC(=O)O)(C1=CC=CC=C1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br-]

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	37/39-26
HS Code	29319090

MSDS

Provider	Language
ACROS	English

Usage And Synthesis

Chemical Properties

white to slightly yellow powder or chunks

Uses

(2-Carboxyethyl)triphenylphosphonium bromide is utilized as a starting reagent in the preparation of activated carbodiimide-triphenylphosphonium complexes and TPP-conjugated lipids[6].

Synthesis

590-92-1

603-35-0

(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM BROMIDE

51114-94-4

GENERAL PROCEDURE: Add 3-bromopropionic acid (5.0 mmol), triphenylphosphine (20.0 mmol) and dry acetonitrile (10.0 mL) to a round bottom flask. The mixture was heated to reflux with vigorous stirring. The heating was stopped after 15 hours of reaction and the reaction solution was concentrated. The residue was washed sequentially with benzene (3 x 10 mL), hexane (10 mL) and ether (2 x 10 mL). After drying, a white crystalline solid 2-carboxyethyltriphenylphosphonium bromide (1.8 g, 87% yield) was obtained. Compounds 6b-d were synthesized according to the preparation of 6a above.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 21, p. 5878 - 5881
[2] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 12304 - 12310
[3] Chemistry of Natural Compounds, 1990, vol. 26, # 4, p. 486 - 487
[4] Khimiya Prirodnykh Soedinenii, 1990, # 4, p. 568 - 569
[5] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 275 - 284
[6] Benien, P., Solomon, M. A., Nguyen, P., Sheehan, E. M., Mehanna, A. S., & D’Souza, G. G. M. (2015). Hydrophobized triphenyl phosphonium derivatives for the preparation of mitochondriotropic liposomes: choice of hydrophobic anchor influences cytotoxicity but not mitochondriotropic effect. Journal of Liposome Research, 26(1), 21–27. https://doi.org/10.3109/08982104.2015.1022557

(2-Carboxyethyl)triphenylphosphonium bromide

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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