| Identification | More | [Name]
Triisopropylsilane | [CAS]
6485-79-6 | [Synonyms]
(ME2CH)3SIH
SILANE IP3H
TIPS
TIS
TRIISOPROPYLSILANE
Tris-isopropylsilane
Triisopropylsilane (TIPS)
Triisopropylsilane [Cas#
tripropan-2-ylsilane
Triisopropylhydrosilane
Triisopropylsilane ,97% | [EINECS(EC#)]
464-880-1 | [Molecular Formula]
C9H22Si | [MDL Number]
MFCD00009657 | [Molecular Weight]
158.36 | [MOL File]
6485-79-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless liquid | [Boiling point ]
84-86 °C/35 mmHg (lit.) | [density ]
0.773 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.434(lit.)
| [Fp ]
99 °F
| [storage temp. ]
Store at RT. | [solubility ]
Benzene (Soluble), Chloroform (Soluble) | [form ]
liquid | [color ]
colorless | [Specific Gravity]
0.773 | [Water Solubility ]
Immiscible with water. | [Hydrolytic Sensitivity]
3: reacts with aqueous base | [Sensitive ]
Moisture Sensitive | [Detection Methods]
GC,NMR | [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 DataBase Reference]
6485-79-6(CAS DataBase Reference) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS02 | [Signal word ]
Warning | [Hazard statements ]
H226 | [Precautionary statements ]
P210-P233-P240-P241-P242-P243 | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
10-21 | [TSCA ]
No | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29319090 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Flam. Liq. 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless liquid | [Uses]
Selective silylation of primary hydroxy groups in the presence of secondary alcohol. | [Uses]
The bulky isopropyl groups (vs. ethyl) allow for more selective reductions, e.g., beta-selective reduction of anomeric C-phenyl ketals, but do not diminish their activity (e.g. in the copper triflate catalyzed reductive etherification of trimethylsilyl ethers). | [Application]
Very sterically-hindered silane. Used as a cation
scavenger in the deprotection of peptides. | [Preparation]
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].
| [Reactivity Profile]
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 | [References]
[1] Emma J. Ste.Marie, Robert J. Hondal. “Reduction of cysteine-S-protecting groups by triisopropylsilane.” Journal of Peptide Science 24 11 (2018). |
|
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J & K SCIENTIFIC LTD.
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Alfa Aesar
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Energy Chemical
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