Triisopropylsilane

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Triisopropylsilane
Triisopropylsilane.svg
Names
Preferred IUPAC name
Tri(propan-2-yl)silane
Other names
TIS or TIPS
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 464-880-1
  • InChI=1S/C9H21Si/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3
    Key: ZGYICYBLPGRURT-UHFFFAOYSA-N
  • CC(C)[Si](C(C)C)C(C)C
Properties
C9H22Si
Molar mass 158.360 g·mol−1
Density 0.773 g/mL
Boiling point 166 °C (331 °F; 439 K)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H315, H317, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 35 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[edit]

  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.