(4-Carboxybutyl)triphenylphosphoniumbromid

Bezeichnung:(4-Carboxybutyl)triphenylphosphoniumbromid

CAS-Nr17814-85-6

Englisch Name:(4-Carboxybutyl)triphenylphosphonium bromide

CBNumberCB2407120

SummenformelC23H24BrO2P

Molgewicht443.31

MOL-Datei17814-85-6.mol

Synonyma

(4-Carboxybutyl)triphenylphosphoniumbromid

(4-Carboxybutyl)triphenylphosphoniumbromid physikalisch-chemischer Eigenschaften

Schmelzpunkt	204-207 °C(lit.)
Siedepunkt	324.7-327.4℃ at 101.93-102.15kPa
chüttdichte	360-400kg/m3
Dichte	1.371 at 20℃
Dampfdruck	0Pa at 25℃
Flammpunkt	195°(383°F)
storage temp.	Store below +30°C.
Löslichkeit	DMSO, Methanol, Water
Aggregatzustand	solid
Farbe	White to Off-White
Wasserlöslichkeit	Soluble in ethanol, methanol and soluble water. Insoluble in toluene and hexane.
Sensitive	Hygroscopic
BRN	3586477
InChI	1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H
InChIKey	KQJPHSBFOSLICV-UHFFFAOYSA-N
SMILES	[Br-].OC(=O)CCCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3
LogP	0.146
CAS Datenbank	17814-85-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
RIDADR	3278
WGK Germany	3
HS Code	29310095
Speicherklasse	6.1D - Non-combustible acute toxic Cat.3 toxic hazardous materials or hazardous materials causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Dam. 1

Gefahreninformationscode (GHS)

(4-Carboxybutyl)triphenylphosphonium bromide Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die 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.
Chemische Eigenschaften
WHITE TO ALMOST WHITE CRYSTALLINE POWDER
Verwenden
- Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells
Reactant for preparation of:
- Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions
- Methyl alkenyl quinolones as antimycobacterial agents
- Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement
- Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents
- Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity
- Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction
Verwenden
suzuki reaction
Verwenden
(4-Carboxybutyl)triphenylphosphonium Bromide (cas# 17814-85-6) is a compound useful in organic synthesis.
reaction suitability
reaction type: C-C Bond Formation
Synthese

2067-33-6

603-35-0

17814-85-6

General method: 5-Bromovaleric acid (1 eq.) and triphenylphosphine (1 eq.) were dissolved in 300 mL of toluene and the reaction was refluxed under argon protection for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The target product 4-carboxybutyltriphenylphosphonium bromide was obtained by crystallization and purification of the residue from a suitable solvent.
Einzelnachweise
[1] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3196 - 3206
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 697 - 704
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[4] Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6353 - 6363

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