Allyltrimethylsilan

Allyltrimethylsilane Struktur
762-72-1
CAS-Nr.
762-72-1
Bezeichnung:
Allyltrimethylsilan
Englisch Name:
Allyltrimethylsilane
Synonyma:
allytrimethylsilane;TRIMETHYLALLYLSILANE;3-(TRIMETHYLSILYL)PROPENE;trimethyl-2-propenyl-Silane;DK892;CA0570;CFS-721;TMS-ALLYL;Co-Formula CFS-721;ALLYLTRIMETHYLSILANE
CBNumber:
CB0431082
Summenformel:
C6H14Si
Molgewicht:
114.26
MOL-Datei:
762-72-1.mol

Allyltrimethylsilan Eigenschaften

Siedepunkt:
84-88 °C (lit.)
Dichte
0.719 g/mL at 25 °C (lit.)
Dampfdruck
82hPa at 25℃
Brechungsindex
n20/D 1.407(lit.)
Flammpunkt:
45 °F
storage temp. 
2-8°C
Löslichkeit
freely sol all organic solvents.
Aggregatzustand
Liquid
Wichte
0.72
Farbe
Clear colorless
Wasserlöslichkeit
insoluble
Hydrolytic Sensitivity
2: reacts with aqueous acid
BRN 
906755
Stabilität:
Volatile
InChIKey
HYWCXWRMUZYRPH-UHFFFAOYSA-N
LogP
4.64 at 20℃
CAS Datenbank
762-72-1(CAS DataBase Reference)
NIST chemische Informationen
Silane, trimethyl-2-propenyl-(762-72-1)
EPA chemische Informationen
Silane, trimethyl-2-propenyl- (762-72-1)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher F,Xi
R-Sätze: 11-36/37/38
S-Sätze: 16-26-36-23-33-7/9
RIDADR  UN 1993 3/PG 2
WGK Germany  3
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29310095
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
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
Sicherheit
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

Allyltrimethylsilan Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

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

S-Sätze Betriebsanweisung:

S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
S7/9:Behälter dicht geschlossen an einem gut gelüfteten Ort aufbewahren.

Chemische Eigenschaften

clear colourless liquid

Verwenden

Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi?Sakurai reaction.

synthetische

Allyltrimethylsilane is synthesized by the reaction of trimethylchlorosilane and allylmagnesium bromide.

Application

Allyltrimethylsilane is used in the allylation of aldehydes, imines, allylic and benzylic alcohols, and chiral α-keto-amides that are derived from (S)-proline esters.

Reaktionen

Allyltrimethylsilane is involved as a reactant in Hosomi Sakurai reaction for allylation in the presence of Lewis acid. For example, it reacts with cyclohexanone to get 1-allylcyclohexanol. It acts as a nucleophile and is involved in Carbon-Ferrier rearrangement.
As a Carbon Nucleophile in Lewis Acid-Catalyzed Reactions.
Allyltrimethylsilane is an alkene some 10 times more nucleophilic than propene, as judged by its reactions with diarylmethyl cations.It reacts with a variety of cationic carbon electrophiles, usually prepared by coordination of a Lewis acid to a functional group, but also by chemical or electrochemical oxidation,or by irradiation in the presence of 9,10- dicyanoanthracene.
carbon to give an intermediate cation, and the silyl group is lost to create a double bond at the other terminus. Among the more straightforward electrophiles are acid chlorides (eq 1).
Allyltrimethylsilane Reactions
As a Carbon Nucleophile in Fluoride Ion-Catalyzed Reactions.
The reactions with aldehydes, ketones (eq 23),54 and α,β-unsaturated esters (eq 24)55 can also be catalyzed by fluoride ion, usually introduced as tetra-n-butylammonium fluoride (TBAF), or other silicophilic ions such as alkoxide. These reactions produce silyl ether intermediates, which are usually hydrolyzed before workup. The stereochemistry of attack on chiral ketones can sometimes be different for the Lewis acid- and fluoride ion-catalyzed reactions.
Other Reactions.
Allyltrimethylsilane reacts with some highly electrophilic alkenes, carbonyl compounds, azo compounds, and singlet oxygen to a greater or lesser extent in ene reactions that do not involve the loss of the silyl group, and hence give vinylsilanes in a solvent-dependent reaction.

läuterung methode

Fractionate it through an efficient column at atmospheric pressure. If impure, dissolve it in THF, shake it with H2O (2x), dry (Na2SO4), filter and fractionate it. [Cudlin & Chvalovsky′ Collect Czech Chem Commun 27 1658 1962, Beilstein 4 IV 3927.]

Allyltrimethylsilan Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Allyltrimethylsilan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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762-72-1(Allyltrimethylsilan)Verwandte Suche:


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  • Allyltrimethylsilane(3-trimethylsilyl-1-propene)99%available
  • Silane,trimethyl-2-propenyl-
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  • ALLYLTRIMETHYLSILANE FOR SYNTHESIS
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  • 3-TRIMETHYLSILYL-1-PROPENE
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  • CA0570
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  • ALLYLTRIMETHYLSILANE
  • 2-(tert-butyloctasulfanyl)-2-methylpropane
  • Co-Formula CFS-721
  • trimethyl-2-propenyl-
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  • Allyltrimethylsilane, 97%, for synthesis
  • Allyltrimethylsilane >
  • Silane, trimethyl-2-propen-1-yl-
  • CAS 762-72-1 Allyltrimethylsilane
  • trimethyl-2-propenyl-Silane
  • 3-(TRIMETHYLSILYL)PROPENE
  • TRIMETHYLALLYLSILANE
  • allytrimethylsilane
  • 762-72-1
  • DK892
  • 762-72-1
  • 62-72-1
  • 792-72-1
  • C6H14Si
  • H2CCHCH2SiCH33
  • CH2CHCH2SiCH33
  • Organometallic Reagents
  • Organosilicon
  • Others
  • ALKYNE
  • Si (Classes of Silicon Compounds)
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Vinylsilanes, Allylsilanes
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Vinylsilanes, Allylsilanes
  • Si (Classes of Silicon Compounds)
  • Synthetic Organic Chemistry
  • Industrial/Fine Chemicals
  • API intermediates
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