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Iodotrimethylsilan

Iodotrimethylsilane Struktur
16029-98-4
CAS-Nr.
16029-98-4
Bezeichnung:
Iodotrimethylsilan
Englisch Name:
Iodotrimethylsilane
Synonyma:
TRIMETHYLSILYL IODIDE;TMIS;TMS iodide;CT3610;IodotrimethyL;Trimethylsilyl io;Iodotrmethylsilane;trimethyiodosilane;Co-Formula CFS-710;iodotrimethyl-silan
CBNumber:
CB0478159
Summenformel:
C3H9ISi
Molgewicht:
200.09
MOL-Datei:
16029-98-4.mol

Iodotrimethylsilan Eigenschaften

Schmelzpunkt:
<0°C
Siedepunkt:
106 °C(lit.)
Dichte
1.406 g/mL at 25 °C(lit.)
Brechungsindex
n20/D 1.471(lit.)
Flammpunkt:
−25 °F
storage temp. 
-20°C
L?slichkeit
reacts
Aggregatzustand
Liquid
Wichte
1.47
Farbe
Clear colorless to reddish
Wasserl?slichkeit
reacts
Sensitive 
Moisture & Light Sensitive
Hydrolytic Sensitivity
8: reacts rapidly with moisture, water, protic solvents
BRN 
1731136
Stabilit?t:
Moisture Sensitive (Reactive)
InChIKey
CSRZQMIRAZTJOY-UHFFFAOYSA-N
CAS Datenbank
16029-98-4(CAS DataBase Reference)
NIST chemische Informationen
Iodotrimethylsilane(16029-98-4)
EPA chemische Informationen
Silane, iodotrimethyl- (16029-98-4)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher F,C
R-S?tze: 11-14-34
S-S?tze: 16-26-36/37/39-43-45-25
RIDADR  UN 2924 3/PG 2
WGK Germany  3
8-21
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 GHS hazard pictogramssrc="/GHS02.jpg" width="20" height="20" /> P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H314 Verursacht schwere Ver?tzungen der Haut und schwere Augensch?den. ?tzwirkung auf die Haut Kategorie 1B Achtung GHS hazard pictogramssrc="/GHS05.jpg" width="20" height="20" /> P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
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.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
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.

Iodotrimethylsilan Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R11:Leichtentzündlich.
R14:Reagiert heftig mit Wasser.
R34:Verursacht Ver?tzungen.

S-S?tze Betriebsanweisung:

S16:Von Zündquellen fernhalten - Nicht rauchen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S43:Zum L?schen . . . (vom Hersteller anzugeben) verwenden (wenn Wasser die Gefahr erh?ht, anfügen: "Kein Wasser verwenden").
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S25:Berührung mit den Augen vermeiden.

Chemische Eigenschaften

Straw liquid

Verwenden

Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.Iodotrimethylsilane is a highly efficient reagent for the cleavage of ethers, esters, carbamates, ketals, and lactones. It is also used for the introduction of TMS groups, such as TMS enol ethers, and is a key reagent for the selective removal of N-Cbz groups in the presence of a trimethyltin moiety.This reagent has recently been reported to convert allyl and benzyl phosphotriesters to the corresponding iodides.

Application

Iodotrimethylsilane can be used as a versatile reagent for the mild dealkylation of ethers, carboxylic esters, lactones, carbamates, acetals, phosphonate and phosphate esters; cleavage of epoxides, cyclopropyl ketones; conversion of vinyl phosphates to vinyl iodides; neutral nucleophilic reagent for halogen exchange reactions, carbonyl and conjugate addition reactions; use as a trimethylsilylating agent for formation of enol ethers, silyl imino esters, and N-silylenamines, alkyl, alkenyl and alkynyl silanes; Lewis acid catalyst for acetal formation, α- alkoxymethylation of ketones, for reactions of acetals with silyl enol ethers and allylsilanes; reducing agent for epoxides, enediones, α-ketols, sulfoxides, and sulfonyl halides; dehydrating agent for oximes.

synthetische

Iodotrimethylsilane is prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes. Other have been reported for the preparation of Trimethylsilyl Iodide(TMS-I): chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°C to afford TMS-I with no byproducts.
synthesis of Iodotrimethylsilane

Reaktionen

Trimethylsilyl iodide reacts under mild conditions in the absence of a catalyst with alkyl fluorides as well as with benzyl and tertiary alkyl chlorides and bromides to give good yields of alkyl iodides and the corresponding trimethylsilyl halides.

Allgemeine Beschreibung

Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.

Synthese

This procedure describes a convenient method for the preparation of Iodotrimethylsilane: A 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60°C as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°C, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140°C to 210°C, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°C.

l?uterung methode

Add a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]

Iodotrimethylsilan Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Iodotrimethylsilan Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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16029-98-4(Iodotrimethylsilan)Verwandte Suche:


  • IODOTRIMETHYLSILANE
  • IODOTRIMETHYLSILYL IODIDE
  • CT3610
  • iodotrimethyl-silan
  • Silane, iodotrimethyl-
  • trimethyliodosilane(tmis)
  • TRIMETHYLIODOSILANE
  • Iodotrmethylsilane
  • Trimethyliodosilanestabilizedwithcoppergranules
  • IODOTRIMETHYLSILANE , STABILIZED WITH COPPER
  • IODO TRIMETHYL SILYL
  • trimethyiodosilane
  • Iodotrimethylsilane, 97%, stab. with copper
  • Trimethylsilyl Iodide (stabilized with Aluminum)
  • IODOTRIMETHYLSILANE, STAB.
  • Iodotrimethylsilane, stabilised with copper, 95%
  • Iodotrimethylsilane, stabilized, 95-97%
  • Trimethyl iodo silane Iodotrimethylsilane
  • Iodotrimethylsilane, 95+%, packaged under Argon in resealable ChemSeal bottles
  • TMIS, Trimethyliodosilane
  • Iodotrimethylsilane, 95-97%, stabilized
  • Iodotrimethylsilane, stabilized
  • Iodotrimethylsilane ,95% [stabilized with copper]
  • Iodotrimethylsilane, stabilized, AcroSeal, 95-97%
  • TriMethyl silane iodine
  • IodotriMethylsilane, 95-97%, stabilized, AcroSeal
  • IodotriMethylsilane, stabilized, 95-97% 100ML
  • Trimethylsilysiodide
  • IodotriMethylsilane, stabilized, 95-97% 25ML
  • IodotriMethylsilane, stabilized, 95-97% 5ML
  • IodotriMethylsilane, stabilized, AcroSeal, 95-97% 100ML
  • Iodotrimethylsilane Trimethyliodosilane
  • IODOTRIMETHYLSILANE FOR SYNTHESIS
  • Trimethylsilyl iodide, TMIS
  • IodotriMethylsilane (>90%)
  • Three Methyl iodide silane
  • Iodotrimethylsilane, 97%, stabilized
  • Iodotrimethylsilane, 95-97%
  • Iodotrimethylsilane, 1.0 M solution in methylene chloride
  • Iodotrimethylsilane, 98%, stabilized with copper, J&KSeal
  • IodotrimethyL
  • IodotriMethylsilane, stabilized, AcroSeal
  • Trimethylsilyl io
  • Co-Formula CFS-710
  • Trimethylsilyl iodide(TMSI)
  • Iodotrimethylsilane, TMIS
  • TrimethylsilylIodide(stabilizedwithAluminum)>
  • trimethyl iodide silane
  • Iodotrimethylsilane, 95-97%, stabilized, AcroSeal&trade
  • TMIS
  • TRIMETHYLSILYL IODIDE
  • TMS iodide
  • lodotrimethylsilane
  • 16029-98-4
  • 1302039
  • C3H9Sil
  • CH33SiI
  • C3H9ISi
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