| Identification | Back Directory | [Name]
(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM BROMIDE | [CAS]
51114-94-4 | [Synonyms]
CET
2-Carboxyethyl triphenylphosponium bromide
2-Carobxyethyl triphenylphosphonium bromide
(2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
2-CARBOXYETHYL TRIPHENYLPHOSPHONIUM BROMIDE 97%
(2-Carboxyethyl)triphenylphosphonium bromide, 97 %
(2-Carboxyethyl)triphenylphosphoniuM broMide, 97% 5GR | [Molecular Formula]
C21H20BrO2P | [MDL Number]
MFCD00031698 | [MOL File]
51114-94-4.mol | [Molecular Weight]
415.26 |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellow powder or chunks | [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-] |
| Hazard Information | Back Directory | [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]
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 |
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