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Triethylsilan

Triethylsilane Struktur
617-86-7
CAS-Nr.
617-86-7
Bezeichnung:
Triethylsilan
Englisch Name:
Triethylsilane
Synonyma:
Et3SiH;Triethylsilyl;Triethylsilyl hydride;PDFF;Silane, triethyl-;Triethylsilicon hydride;NSC 93579;Co-Formula CFS-867;Medetomidine Impurity 40;Triethylsilane,Triethylsilyl hydride
CBNumber:
CB8495938
Summenformel:
C6H16Si
Molgewicht:
116.28
MOL-Datei:
617-86-7.mol

Triethylsilan Eigenschaften

Schmelzpunkt:
-157°C
Siedepunkt:
107-108 °C (lit.)
Dichte
0.728 g/mL at 25 °C (lit.)
Dampfdruck
>1 hPa (20 °C)
Brechungsindex
n20/D 1.412(lit.)
Flammpunkt:
25 °F
storage temp. 
Store below +30°C.
L?slichkeit
insol H2O; sol hydrocarbons, halocarbons, ethers.
Aggregatzustand
liquid
Farbe
colorless
Wichte
0.728
Wasserl?slichkeit
Miscible with water.
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
3: reacts with aqueous base
BRN 
1098278
Stabilit?t:
Stable, but moisture sensitive. Highly flammable. Generates highly flammable gas (hydrogen) in contact with water, acids and bases.
InChI
1S/C6H16Si/c1-4-7(5-2)6-3/h7H,4-6H2,1-3H3
InChIKey
AQRLNPVMDITEJU-UHFFFAOYSA-N
SMILES
CC[SiH](CC)CC
LogP
3.6 at 20℃
CAS Datenbank
617-86-7(CAS DataBase Reference)
NIST chemische Informationen
Silane, triethyl-(617-86-7)
EPA chemische Informationen
Triethylsilane (617-86-7)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher F,Xi
R-S?tze: 11-36/37/38-52/53
S-S?tze: 9-16-29-33-37/39-26-61
RIDADR  UN 1993 3/PG 2
WGK Germany  1
10-21
TSCA  TSCA listed
HazardClass  3
PackingGroup  II
HS Code  29310095
Speicherklasse 3 - Flammable liquids
Hazard Classifications Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3
Bildanzeige (GHS) Flame (GHS02)Exclamation Mark (GHS07)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizit?t (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
Sicherheit
P210 Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P233 Beh?lter dicht verschlossen halten.
P240 Beh?lter und zu befüllende Anlage erden.
P241 Explosionsgeschützte [elektrische/Lüftungs-/ Beleuchtungs-/...] Ger?te verwenden.
P303+P361+P353 BEI BERüHRUNG MIT DER HAUT (oder dem Haar): Alle kontaminierten Kleidungsstücke sofort ausziehen. Haut mit Wasser abwaschen oder duschen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen.

Triethylsilan Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R11:Leichtentzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze Betriebsanweisung:

S9:Beh?lter an einem gut gelüfteten Ort aufbewahren.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S29:Nicht in die Kanalisation gelangen lassen.
S33:Ma?nahmen gegen elektrostatische Aufladungen treffen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Beschreibung

Triethylsilane is a useful versatile reductant since it has a active hydride. It can be used for mediated the palladium-catalyzed dehalogenation reaction of alkyl or aryl halides, the reduction of primary, secondary, and tertiary chlorides, bromides, and iodides catalyzed by iridium, as well as efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection. It is also specifically for the hydrosilation of olefins to give alkyl silanes. It is also the catalyst for synthesis of a spiro-oxindole blocker of Nav1.7 for the treatment of pain, redox initiated cationic polymerization and Beckmann rearrangement of cyclododecanone oxime as well as regioselective reductive coupling of enones and allenes.

Chemische Eigenschaften

Clear liquid

Verwenden

Triethylsilane is a trialkylsilicon hydride used in the synthesis of alkylsilanes via hydrosilation of olefins. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.

Vorbereitung Methode

A synthetic method of triethylsilane comprises the following steps: reacting sodium hydride with trimethyl borate to prepare trimethoxy sodium borohydride; adding triethylchlorosilane to trimethoxy sodium monohydroborate to react to obtain triethylsilane.
To a 500ml reaction flask, 20g (0.5mol) of 60% sodium hydride and 80g of anhydrous tetrahydrofuran were added. Stirring and cooling to 0-10 ℃ under the protection of nitrogen, the mixture was then maintained under nitrogen protection, stirred, and the liquid temperature at 0-10 ℃, and dropwise added 57.2g (0.55mol) of trimethyl borate. After the dropwise addition, the temperature was kept at 0-10 ℃ and stirred for 1 hour.Maintaining the nitrogen protection, stirring and liquid temperature of the reaction liquid at 0-10 ℃, and then dropwise adding 67.7g (0.45mol) of triethylchlorosilane. After the dropwise addition, continuously keep the temperature at 0-10 ℃ and stir for 1 hour. The reaction solution was then filtered at room temperature. Rectifying the filtrate at normal pressure and collecting fractions with the boiling range of 109-110 ℃ as triethylsilane to obtain 46.1g of triethylsilane, which yields 88.2%. 45-64 ℃: a mixed solution of trimethyl borate and tetrahydrofuran; 64-109 ℃:a mixture of tetrahydrofuran and a small triethylsilane.

Definition

ChEBI: Triethylsilane is an organosilicon compound. It has a role as a reducing agent.

Application

Triethylsilane is used as a reducing agent inmany organic synthetic reactions.
Used to reduce metal salts. Enhances deprotection of t-butoxycarbonyl-protected amines and tert-butylesters.
Used in the reductive amidation of oxazolidinones with amino acids to provide dipeptides.
Converts aldehydes to symmetrical and unsymmetrical ethers.
Used in the "in-situ" preparation of diborane and haloboranes.

Brandgefahr

Highly flammable; flash point -4°C (25°F) (Aldrich 1996).
It does not ignite spontaneously in air, but it can explode on heating. The ease of oxidation of this compound is relatively lower than mono- and dialkylsilanes. Reaction with oxidizing substances, however, can be violent. Reaction with boron trichloride could be explosive at room temperature. Even at 78°C ( 108°F), mixing these reagents caused pressure buildup and combustion (Matteson 1990).

l?uterung methode

Reflux triethylsilane over molecular sieves, then distil it. It is passed through neutral alumina before use [Randolph & Wrighton J Am Chem Soc 108 3366 1986]. [Beilstein 4 IV 3895.]

Triethylsilan Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Triethylsilan Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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  • CH3CH23SiH
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  • Synthetic Reagents
  • Silicon Compounds (for Synthesis)
  • Reduction
  • Si-H Compounds
  • Si (Classes of Silicon Compounds)
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