Triisopropylsilane Chemical Properties

Boiling point:

84-86 °C/35 mmHg (lit.)

Density 

0.773 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.434(lit.)

Flash point:

99 °F

storage temp. 

Store below +30°C.

solubility 

Benzene (Soluble), Chloroform (Soluble)

form 

liquid

Specific Gravity

0.773

color 

colorless

Water Solubility 

Immiscible with water.

Sensitive 

Moisture Sensitive

Hydrolytic Sensitivity

3: reacts with aqueous base

BRN 

1733718

InChIKey

YDJXDYKQMRNUSA-UHFFFAOYSA-N

CAS DataBase Reference

6485-79-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Triisopropylsilane Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

Selective silylation of primary hydroxy groups in the presence of secondary alcohol.

Uses

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.

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).
[2]Aoyagi, K.; Ohmori, Y.; Inomata, K.; Matsumoto, K.; Shimada, S.; Sato, K.; Nakajima, Y., Chem. Commun. 2019, 55, 5859.

Triisopropylsilane(6485-79-6)Related Product Information

• N,N-Diisopropylethylamine
• 3-Chloropropyltrimethoxysilane
• 3-Aminopropyltrimethoxysilane
• Trimethoxypropylsilane
• N-Methyl-2-pyrrolidone
• Triethoxypropylsilane
• Trimethoxysilylpropanethiol
• 3-Mercaptopropyltriethoxysilane
• Triisopropylsilyl chloride
• ISOPROPYLTRICHLOROSILANE
• Isoproterenol
• Triethoxyvinylsilane
• (TRIISOPROPYLSILYL)ACETYLENE
• TRIISOPROPOXYSILANE
• Chlorotriethylsilane
• Triethylsilane
• Triisopropyl phosphite
• Triisopropyl borate