Triisopropylsilane

Bezeichnung:Triisopropylsilane

CAS-Nr6485-79-6

Englisch Name:Triisopropylsilane

CBNumberCB7208472

SummenformelC9H22Si

Molgewicht158.36

MOL-Datei6485-79-6.mol

Triisopropylsilane physikalisch-chemischer Eigenschaften

Siedepunkt	84-86 °C/35 mmHg (lit.)
Dichte	0.773 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.434(lit.)
Flammpunkt	99 °F
storage temp.	Store below +30°C.
Löslichkeit	Benzene (Soluble), Chloroform (Soluble)
Aggregatzustand	liquid
Wichte	0.773
Farbe	colorless
Wasserlöslichkeit	Immiscible with water.
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	3: reacts with aqueous base
BRN	1733718
InChI	1S/C9H22Si/c1-7(2)10(8(3)4)9(5)6/h7-10H,1-6H3
InChIKey	YDJXDYKQMRNUSA-UHFFFAOYSA-N
SMILES	CC(C)[SiH](C(C)C)C(C)C
CAS Datenbank	6485-79-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	10-36/37/38
S-Sätze:	26-36-37/39-16
RIDADR	UN 1993 3/PG 3
WGK Germany	3
F	10-21
TSCA	No
HS Code	2931 90 00
HazardClass	3
PackingGroup	III
Speicherklasse	3 - Flammable liquids
Hazard Classifications	Flam. Liq. 3

Gefahreninformationscode (GHS)

Triisopropylsilane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R10:Entzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze 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.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Chemische Eigenschaften
Clear colorless liquid
Verwenden
Selective silylation of primary hydroxy groups in the presence of secondary alcohol.
Verwenden
Triisopropylsilane is used as a protecting group in peptide synthesis and is also used as a reducing agent for the selective reduction of anomeric C-phenyl ketals. It is used in the selective silylation of primary hydroxyl groups without affecting the secondary hydroxyl group. It is used in the preparation of anti-1,2-diols catalyzed by a Ni(O) N-heterocyclic carbine complex with high diastereoselectivity.
Application
Triisopropylsilane is a very sterically-hindered silane. Used as a cation scavenger in the deprotection of peptides.
synthetische
Triisopropylsilane can be prepared by reduction of chlorotriisopropylsilane or by reduction of triisopropylmethoxysilane using lithium aluminum hydride or DIBAL-H. The reduction of triisopropylmethoxysilane using sodium borohydride also forms triisopropylsilane in 32% yield[2].
Reaktivität anzeigen
Hindered hydrosilanes such as triisopropylsilane (TIS) are commonly used as cation scavengers in the deprotection of amino acid side-chains following solid‐phase peptide synthesis (SPPS). Protecting groups such as trityl (Trt) and tert‐butyl (But ) form stable cations upon acidolysis and are easily removed from N‐, O‐, and S‐containing amino acid side‐chains (for cysteine (Cys) But is not easily removed). In acid, TIS drives the equilibrium towards cleavage of the protecting group from the amino acid side chain by donating a hydride to the resulting cation in an irreversible manner. Although TIS and other hindered hydrosilanes are exclusively thought of as protecting group scavengers in SPPS, they are actually mild reducing agents. They can reduce a carbon‐heteroatom bond and can, therefore, directly participate in the removal of a protecting group from an amino acid side‐chain[1].
reaction suitability
reagent type: reductant
Einzelnachweise
[1] Emma J. Ste.Marie, Robert J. Hondal. “Reduction of cysteine-S-protecting groups by triisopropylsilane.”Journal of Peptide Science 24 11 (2018).
[2]Aoyagi, K.; Ohmori, Y.; Inomata, K.; Matsumoto, K.; Shimada, S.; Sato, K.; Nakajima, Y., Chem. Commun. 2019, 55, 5859.

Triisopropylsilane Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

6485-79-6, Triisopropylsilane Verwandte Suche:

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