Triisopropylsilane

Triisopropylsilane
Names
	Other names TIS or TIPS
Identifiers
CAS Number	6485-79-6;
3D model (JSmol)	Interactive image;
ChemSpider	122362;
EC Number	464-880-1;
PubChem CID	6327611;
	InChI InChI=1S/C9H21Si/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3 Key: ZGYICYBLPGRURT-UHFFFAOYSA-N;
	SMILES CC(C)[Si](C(C)C)C(C)C;
Properties
Chemical formula	C9H22Si
Molar mass	158.360 g·mol−1
Density	0.773 g/mL
Boiling point	166 °C (331 °F; 439 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H315, H317, H319, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P370+378, P403+233, P403+235
Flash point	35 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Triisopropyl silane (TIPS) is an organosilicon compound with the formula (i-Pr)₃SiH (i-Pr = isopropyl). This colorless liquid is used as a scavenger in peptide synthesis. It can also act as a mild reducing agent.

In peptide synthesis, TIPS is used as a scavenger for peptide groups being removed from the peptide sequence at the global deprotection. TIPS is able to scavenge carbocations formed in the deprotection of a peptide as it can act as a hydride donor in acidic conditions.[1] Silanes may be preferred as scavengers in place of sulfur-based scavengers.

References

Pearson, Daniel A.; Blanchette, Mary; Baker, Mary Lou; Guindon, Cathy A. (1989). "Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis". Tetrahedron Letters. 30 (21): 2739–2742. doi:10.1016/s0040-4039(00)99113-5.

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[1] Pearson, Daniel A.; Blanchette, Mary; Baker, Mary Lou; Guindon, Cathy A. (1989). "Trialkylsilanes as scavengers for the trifluoroacetic acid deblocking of protecting groups in peptide synthesis". Tetrahedron Letters. 30 (21): 2739–2742. doi:10.1016/s0040-4039(00)99113-5.