Azidotrimethylsilan

Bezeichnung:Azidotrimethylsilan

CAS-Nr4648-54-8

Englisch Name:Azidotrimethylsilane

CBNumberCB3444416

SummenformelC3H9N3Si

Molgewicht115.21

MOL-Datei4648-54-8.mol

Synonyma

Azidotrimethylsilan

Azidotrimethylsilan physikalisch-chemischer Eigenschaften

Schmelzpunkt	-95°C
Siedepunkt	92-95 °C(lit.)
Dichte	0.876 g/mL at 20 °C(lit.)
Brechungsindex	n20/D 1.415(lit.)
Flammpunkt	74 °F
storage temp.	2-8°C
Löslichkeit	Miscible with toluene, dichloromethane, diethyl ether and most organic solvents.
Aggregatzustand	Liquid
Wichte	0.868
Farbe	Clear colorless to slightly yellow
Wasserlöslichkeit	decomposes
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	8: reacts rapidly with moisture, water, protic solvents
BRN	1903730
InChIKey	SEDZOYHHAIAQIW-UHFFFAOYSA-N
CAS Datenbank	4648-54-8(CAS DataBase Reference)
NIST chemische Informationen	Azidotrimethylsilane(4648-54-8)
EPA chemische Informationen	Azidotrimethylsilane (4648-54-8)

Sicherheit

Kennzeichnung gefährlicher	F,T,N
R-Sätze:	11-23/24/25-50/53-29
S-Sätze:	16-36/37/39-45-8-57-36/37-29
RIDADR	UN 1992 3/PG 2
WGK Germany	3
F	10-33
Selbstentzündungstemperatur	300 °C
TSCA	Yes
HazardClass	3
PackingGroup	II
HS Code	29310095

Gefahreninformationscode (GHS)

Azidotrimethylsilane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R50/53:Sehr giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R29:Entwickelt bei Berührung mit Wasser giftige Gase.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S8:Behälter trocken halten.
S57:Zur Vermeidung einer Kontamination der Umwelt geeigneten Behälter verwenden.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S29:Nicht in die Kanalisation gelangen lassen.
Chemische Eigenschaften
clear colorless to slightly yellow liquid
Physikalische Eigenschaften
bp 95–96°C; n20 D 1.416; d 0.868 g cm?3; fp23°C; IR νmax 2100 cm?1; 1H NMR (CDCl3) δ = 0.22.
Verwenden
Trimethylsilyl azide is used as an azidonation reagent for amines, amides, aldehydes and ketones. It is involved in the preparation of alfa- and beta-siloxy azides from carbonyl compounds and epoxides. It is also used in the preparation of heterocyclic compounds and also acts as an effective substitute for hydrazoic acid. Further, it is used in the Oseltamivir total synthesis.
Verwenden
Versatile azidonation reagent for amines, amides, aldehydes, and ketones.
Verwenden
Many applications of TMSA in organic synthesis have been reported but only representative examples are described herein. Substitution Reactions. Benzyl,allyl,and substituted alkyl halides are converted to the corresponding azides in 60–100% yields via reactions with TMSA under neutral conditions in a nonaqueous solvent (eq 1).By using tin(IV) chloride as a catalyst, secondary and tertiary cyclic and polycyclic halides are similarly transformed into the corresponding azides in 50–92% yields (eq 1).
synthetische
several methods for the synthesis of this azide have been reported.The procedure involving aluminum chloride is not recommended, since an explosive product is formed.Azidotrimethylsilane is now commercially available, and a representative synthetic procedure is as follows. A mixture of sodium azide and chlorotrimethylsilane is refluxed in di-n-butyl ether for 2 days and the azide is safely distilled directly from the reaction vessel. Purer compound (99% content) is obtained by redistillation of the product. Several improved conditions have been reported for the preparation of this azide.In these procedures, trimethylsilyl chloride is reacted with sodium azide either neat or in a high boiling point solvent, such as a mixture of silicone oil and polyethylene glycol. Distillation of the crude product usually provides trimethylsilyl azide (TMSA) in high purity (97.9%) and yield (97%).
läuterung methode
Distil the azide through a Vigreux column (p 11) in a N2 atmosphere maintaining the oil bath temperature thermostat at 135-140o . Check the purity by 1H NMR [CHCl3, : single peak at 13cps from Me4Si]. Likely impurities are siloxane hydrolysis products. The azide is thermally stable even at 200o when it decomposes slowly without explosive violence. All the same, it is advisable to carry out the distillation behind a thick safety screen in a fumehood because unforseen EXPLOSIVE azides may be formed on long standing. [Birkofer & Wagner Org Synth Coll Vol VI 1030 1988.]

Azidotrimethylsilane Upstream-Materialien And Downstream Produkte

Azidotrimethylsilan Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

4648-54-8, Azidotrimethylsilane Verwandte Suche:

Send Inquriy