Triisopropylsilanethiol

Base Information

• Chemical Name: Triisopropylsilanethiol
• CAS No.: 156275-96-6
• Molecular Formula: C9H22SSi
• Molecular Weight: 190.425
• European Community (EC) Number: 683-644-0
• DSSTox Substance ID: DTXSID80392455
• Nikkaji Number: J1.169.587F
• Wikidata: Q72513654
• Mol file: 156275-96-6.mol

Synonyms:Triisopropylsilanethiol;156275-96-6;tri(propan-2-yl)-sulfanylsilane;tris(propan-2-yl)silanethiol;Silanethiol,1,1,1-tris(1-methylethyl)-;Silanethiol, tris(1-methylethyl)-;triisopropylsilyl thiol;triisopropyl silanethiol;triisopropyl-silanethiol;triisopropylsilane thiol;TIPS-SH;Triisopropylsilane-thiol;SCHEMBL7141;Triisopropylsilanethiol, 97%;DTXSID80392455;CPKHFNMJTBLKLK-UHFFFAOYSA-N;MFCD00216593;AKOS015912197;AS-64344;CS-0187703;FT-0705590;E73930;EN300-7423687;J-009291

Chemical Property of Triisopropylsilanethiol

Chemical Property:

• Vapor Pressure: 0.277mmHg at 25°C
• Refractive Index: n20/D 1.479(lit.)
• Boiling Point: 210.6 °C at 760 mmHg
• PKA: 9.86±0.10(Predicted)
• Flash Point: 81.2 °C
• PSA: 38.80000
• Density: 0.835 g/cm³
• LogP: 4.09170
• Solubility.: Soluble in most organic solvents.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 190.12114841
• Heavy Atom Count: 11
• Complexity: 97

Purity/Quality:

98%,99%, ^*data from raw suppliers

Triisopropylsilanethiol 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si](C(C)C)(C(C)C)S
• Physical properties: bp 70–73 °C (2 mmHg); d 0.887 g cm?3.
• Uses: Triisopropylsilanethiol is convenient synthetic equivalent of H2S for the synthesis of alkanethiols and unsymmetrical dialkyl sulfides; used as polarityreversal catalyst in radical reactions.1. Use as a Nucleophile: A Synthetic Equivalent of H2S. HSTIPS is prepared in quantitative yield (98%) from the reaction of LiSH (readily obtained by reacting H2S with n-BuLi in THF) with TIPSCl at ?78°C.2.Synthesis of 9-BBN-derived Alkyl and Aryl Boranes.3.Palladium-catalyzed Cross-coupling Reactions. The Pd0- catalyzed cross-coupling of vinyl and aryl halides with KSTIPS affords the corresponding silyl sulfides, which can be used either to prepare thiols or sulfides.4.Use as Ligand in Ziegler-Natta Polymerization of Ethylene in Solution. A medium pressure process for the polymerization of ethylene has been developed in the presence of a catalytic system involving a monocyclopentadienyl titanium species, containing TIPSthiolate as the heteroligand and two activable ligands (2Cl or 2Me), associated with an ionic activator such as triphenylcarbenium tetrakis(pentafluorophenyl)borate.5.Use in Radical Reactions. The radical reduction of alkyl halides by silanes is promoted by thiols. According to Roberts, the thiol acts as a polarity-reversal catalyst.6.

Technology Process of Triisopropylsilanethiol

There total 3 articles about Triisopropylsilanethiol 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: 98.0%

triisopropylsilyl chloride (13154-24-0) → triisopropylsilanethiol (156275-96-6)

Guidance literature:

With n-butyllithium; hydrogen sulfide; In tetrahydrofuran; 1.) -78 up to 0 deg C, 0.5 h; 2.) -78 deg C, 0.5 h; 3.) up to RT;

DOI:10.1016/S0040-4039(00)76869-9

Reference yield: 74.0%

chlorotriisopropylsilane (6485-79-6) → triisopropylsilanethiol (156275-96-6)

Guidance literature:

With carbon oxide sulfide; trans-di-O-tert-butyl hyponitrite; In 1,4-dioxane; at 60 ℃; under 1875.15 Torr;

DOI:10.1016/S0040-4039(00)02109-2

Reference yield:

Si(C3H7)3S(2)H → triisopropylsilanethiol (156275-96-6)

Guidance literature:

With triethylsilane; O-(tert-butyl)hydroxylamine; In Cyclohexane-d12; at 50 ℃; Kinetics;

DOI:10.1039/b206552p

upstream raw materials:

triisopropylsilyl chloride

chlorotriisopropylsilane

Downstream raw materials:

phenyl triisopropylsilyl sulfide

triisopropyl(2-(p-tolylethynyl)phenylthio)silane

ethyl-(6-triisopropylsilanylsulfanyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester

4-(2-tri-iso-propylsilanylsulfanyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Schuepbach, Bjoern,Terfort, Andreas. "A divergent synthesis of oligoarylalkanethiols with Lewis-basic N-donor termini". scheme or table. p. 3552 - 3562. Retrieved 2010/08/21.
• 2、 Cai, Yudong,Roberts, Brian P.. "Formation of silanethiols by reaction of silanes with carbonyl sulfide: Implications for radical-chain reduction of thiocarbonyl compounds by silanes". . p. 763 - 766. Retrieved 2007/10/03.