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Tetrabutylammoniumiodid

Tetrabutylammonium iodide Struktur
311-28-4
CAS-Nr.
311-28-4
Bezeichnung:
Tetrabutylammoniumiodid
Englisch Name:
Tetrabutylammonium iodide
Synonyma:
TBAI;TETRA-N-BUTYLAMMONIUM IODIDE;Tetrabutylazanium iodide;Tetrabutylammonium i;etrabutylazanium,iodide;%, SLR, Fisher Chemical;Dronedarone Impurity 52;Tetrabutylaminium·iodide;tetrabutyl-ammoniuiodide;Tetrabutylammonium Iodid
CBNumber:
CB0187592
Summenformel:
C16H36IN
Molgewicht:
369.37
MOL-Datei:
311-28-4.mol

Tetrabutylammoniumiodid Eigenschaften

Schmelzpunkt:
141-143 °C(lit.)
Siedepunkt:
145.3℃[at 101 325 Pa]
Dichte
1.20
Dampfdruck
0Pa at 25℃
storage temp. 
Store below +30°C.
L?slichkeit
acetonitrile: 0.1 g/mL, clear, colorless
Aggregatzustand
Crystalline Powder
Farbe
White to cream
Geruch (Odor)
Amine like
Wasserl?slichkeit
Soluble in water and methanol. Insoluble in benzene.
Sensitive 
Light Sensitive & Hygroscopic
maximale Wellenl?nge (λmax)
λ: 290 nm Amax: 0.1
λ: 300 nm Amax: 0.05
λ: 320 nm Amax: 0.02
λ: 500 nm Amax: 0.02
BRN 
3916152
Expositionsgrenzwerte
ACGIH: TWA 0.01 ppm
Stabilit?t:
Stable. Incompatible with strong oxidizing agents. Light-sensitive.
InChIKey
DPKBAXPHAYBPRL-UHFFFAOYSA-M
LogP
0.869 at 25℃
CAS Datenbank
311-28-4(CAS DataBase Reference)
EPA chemische Informationen
Tetrabutylammonium iodide (311-28-4)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn
R-S?tze: 22-36/37/38
S-S?tze: 26-36-37/39
WGK Germany  3
RTECS-Nr. BS5450000
8
TSCA  Yes
HS Code  29239000
Toxizit?t LD50 orally in Rabbit: 1990 mg/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Tetrabutylammoniumiodid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

Beschreibung

Tetrabutylammonium iodide is a organic ammonium compound, for which all four valences of a nitrogen atom are bonded organically. It is often used as phase-transfer catalysts and ion pair reagents.

Chemische Eigenschaften

Tetrabutylammonium iodide is an organic ammonium compound with the molecular formula C16H36IN. white or tan powder. Soluble in water and ethanol, slightly soluble in chloroform and benzene. Stable under normal temperature and pressure.

Verwenden

Tetrabutylammonium iodide is used in the preparation of novel quaternary amines to serve as antibacterial agents in the rise of drug-resistant bacteria,it is also used in phosphonium reversible inhibitors of cholinesterases.

Reaktionen

Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:
Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.
Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.
Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.
Other reactions where TBAI can be used as a catalyst:
TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.
Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.
Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.

Allgemeine Beschreibung

Tetrabutylammonium iodide is a quaternary ammonium salt used in phase-transfer reactions. It is also used in regioselective ether cleavage reactions and as a source of iodide for nucleophilic displacement reactions.

l?uterung methode

Crystallise the iodide from toluene/pet ether (see entry for the corresponding bromide), acetone, ethyl acetate, EtOH/diethyl ether, nitromethane, aqueous EtOH or water. Dry it at room temperature under a vacuum. It has also been dissolved in MeOH/acetone (1:3, 10mL/g), filtered and allowed to stand at room temperature to evaporate to ca half its original volume. Distilled water (1mL/g) is then added, and the precipitate is filtered off and dried. It can also be dissolved in acetone, precipitated by adding ether and dried in a vacuum at 90o for 2 days. It has also been recrystallised from CH2Cl2/pet ether or hexane, or anhydrous methanol and stored in a vacuum desiccator over H2SO4. [Chau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 558.]

Tetrabutylammoniumiodid Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Tetrabutylammoniumiodid Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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