(5-Carboxypentyl)(triphenyl)phosphonium bromide

Bezeichnung:(5-Carboxypentyl)(triphenyl)phosphonium bromide

CAS-Nr50889-29-7

Englisch Name:(5-Carboxypentyl)(triphenyl)phosphonium bromide

CBNumberCB5259203

SummenformelC24H26BrO2P

Molgewicht457.34

MOL-Datei50889-29-7.mol

(5-Carboxypentyl)(triphenyl)phosphonium bromide physikalisch-chemischer Eigenschaften

Schmelzpunkt	197-201 °C
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Soluble in Chloroform and Methanol.
Aggregatzustand	Solid
Farbe	White to Off-White
Sensitive	Hygroscopic
InChI	InChI=1S/C24H25O2P.BrH/c25-24(26)19-11-4-12-20-27(21-13-5-1-6-14-21,22-15-7-2-8-16-22)23-17-9-3-10-18-23;/h1-3,5-10,13-18H,4,11-12,19-20H2;1H
InChIKey	JUWYRPZTZSWLCY-UHFFFAOYSA-N
SMILES	[P+](CCCCCC(=O)O)(C1C=CC=CC=1)(C1=CC=CC=C1)C1C=CC=CC=1.[Br-]
CAS Datenbank	50889-29-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-20/21/22
S-Sätze:	26-36-36/37/39-22
WGK Germany	3
HS Code	2931599090

Gefahreninformationscode (GHS)

(5-Carboxypentyl)(triphenyl)phosphonium bromide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S22:Staub nicht einatmen.
Chemische Eigenschaften
White Crystalline Solid
Verwenden
(5-Carboxypentyl)(triphenyl)phosphonium bromide is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.
Reactant for:
1. Preparation of inhibitor of protein tyrosine phosphatase 1B for treatment of diabetes and obesity.
2. Synthesis of folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity.
3. Preparation of peptide nucleic acids (PNA) with high specific activity.
4. Synthesis of roseophilin via Wittig/aldol methodology.
Verwenden
It is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.
Synthese

4224-70-8

603-35-0

50889-29-7

General procedure for the synthesis of 5-carboxypentyltriphenylphosphonium bromide from 6-bromohexanoic acid and triphenylphosphine: 6-bromohexanoic acid (10.00 g, 51.27 mmol) and triphenylphosphonium (14.12 g, 53.83 mmol) were dissolved in freshly distilled acetonitrile (50 mL) and the reaction mixture refluxed for 48 h under vigorous stirring. Upon completion of the reaction, the solution was cooled to room temperature and precipitation of Wittig salt was induced by scraping the inner wall of the glass reactor. The resulting white solid product was collected by filtration and washed with ether to give the final 5-carboxypentyltriphenylphosphonium bromide in 98% (22.87 g) yield. The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD): δ 1.62-1.72 (m, 6H), 2.29 (t, 2H), 3.40-3.47 (m, 2H), 7.76-7.91 (m, 15H).
Einzelnachweise
[1] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 321 - 330
[2] Analytical Chemistry, 2006, vol. 78, # 1, p. 71 - 81
[3] Journal of Organic Chemistry, 2004, vol. 69, # 14, p. 4615 - 4625
[4] Journal of Natural Products, 2001, vol. 64, # 11, p. 1426 - 1429
[5] Patent: WO2008/30532, 2008, A2. Location in patent: Page/Page column 41

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