Triisopropylsilane

Base Information

• Chemical Name: Triisopropylsilane
• CAS No.: 6485-79-6
• Molecular Formula: C9H22Si
• Molecular Weight: 158.359
• Hs Code.: 2931 90 00
• European Community (EC) Number: 613-702-2,464-880-1
• DSSTox Substance ID: DTXSID90983439
• Wikipedia: Triisopropylsilane
• Mol file: 6485-79-6.mol

Synonyms:Triisopropylsilane;6485-79-6;6459-79-6;tris(propan-2-yl)silane;Benzenesulfonic acid,5-[(4-amino-1-naphthalenyl)azo]-2-[2-[4-[(2-hydroxy-1-naphthalenyl)azo]-2-sulfophenyl]ethenyl]-,disodium salt (9CI);tri(propan-2-yl)silicon;Triisopropylsilane, 98%;triisopropylsilicon;MFCD00009657;DTXSID90983439;Aksci Bulk ReagentTriisopropylsilane;AMY42278;AKOS006222744;AKOS030228028;AS-19155;PD118098;CS-0017846;FT-0652371;FT-0688183;T1533;A14931;EC 464-880-1;EN300-117959;S17975;A834823;A834907;J-525100;2,2'-Stilbenedisulfonic acid, 4-[(4-amino-1-naphthyl)azo]-4'-[(2-hydroxy-1-naphthyl)azo]-, disodium salt;Benzenesulfonic acid, 5-[(4-amino-1-naphthalenyl)azo]-2-[2-[4-[(2-hydroxy-1-naphthalenyl)azo]-2-sulfophenyl]ethenyl]-, disodium salt

Chemical Property of Triisopropylsilane

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 1.37mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 177.8 °C at 760 mmHg
• Flash Point: 37.2 °C
• PSA: 0.00000
• Density: 0.7726
• LogP: 3.44350
• Storage Temp.: Store at RT.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Immiscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 157.141252204
• Heavy Atom Count: 10
• Complexity: 65.7

Purity/Quality:

99.0% ^*data from raw suppliers

Triisopropylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Silicon)
• Canonical SMILES: CC(C)[Si](C(C)C)C(C)C
• 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). Selective silylation of primary hydroxy groups in the presence of secondary alcohol. 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.

Technology Process of Triisopropylsilane

There total 21 articles about Triisopropylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

isopropyl chloride (75-29-6) → chlorotriisopropylsilane (6485-79-6)

Guidance literature:

With trichlorosilane; magnesium; 1) THF, 2) 0 deg C, 3) 25 deg C, 3d;

DOI:10.1021/jo01311a058

Reference yield: 69.0%

1,1,2,2-tetraisopropyl-1,2-dihydrodisilane (19753-69-6) → di-isopropylsilane (18209-66-0) + chlorotriisopropylsilane (6485-79-6) + 2,2,4-Triisopropyl-[1,3,2,4]dithiadisiletane + 2,2,4,4-Tetraisopropyl-1,3,2,4-dithiadisiletan

Guidance literature:

With sulfur; at 320 ℃; for 8h;

DOI:10.1016/S0022-328X(00)90001-9

Reference yield: 64.0%

trichlorosilane (10025-78-2) + isopropyllithium (1888-75-1) → chlorotriisopropylsilane (6485-79-6)

Guidance literature:

In benzine; HSiCl3 and i-C3H7Li in benzine at -5°C;;

upstream raw materials:

isopropyllithium

isopropyl chloride

1,1,2,2-tetraisopropyl-1,2-dihydrodisilane

1,1,1-trichloro-2-methyl-1-silapropane

Downstream raw materials:

ethylbenzene

trans-2-triisopropylsilyl-1-phenylethylene

triisopropylsilyl trifluoromethanesulfonate

p-benzylanizole

Refernces

Organotransition-metal-modified sugars Part 17. Glucal-derived carbene complexes: syhthesis and diastereoselective benzannulation

10.1016/S0022-328X(00)00748-8

The research focuses on the synthesis and diastereoselective benzannulation of glucal-derived carbene complexes involving organotransition-metal-modified sugars. The study utilizes stannylated precursors 5 and 6 to prepare triisopropylsilyl and isopropylidene-protected 1-lithio-D-glucals, which react with hexacarbonyl chromium and subsequent methylation to yield D-arabino-hex-1-enopyranosylcarbene complexes 7 and 8. These complexes then undergo diastereoselective benzannulation with tolan and 3-hexyne to produce polyoxygenated chromans 9 to 12. The research emphasizes the role of protective groups in controlling the conformation of the glucal moiety in both the carbene ligand and the chroman skeleton. The study employs 1H-NMR studies and single crystal X-ray analyses to determine the conformations of the sugar moiety in solution and solid state, indicating a 5H4-conformation for triisopropylsilyl compounds and a 4H5-conformation for isopropylidene derivatives. The reactions and analyses involve various reagents, protective groups, and spectroscopic techniques, with a particular focus on the stereochemistry and conformational control in the synthesis of these complex organic molecules.