Tris(propan-2-yl)silanethiol (HCID 3435097)

Names & identifiers

Preferred name: Tris(propan-2-yl)silanethiol
IUPAC: tri(propan-2-yl)-sulfanylsilane
English name: TRIISOPROPYLSILANETHIOL
Molecular formula: C9H22SSi
Molecular weight: 190.42

Names & synonyms

tris(propan-2-yl)silanethiolRefChem:900373683-644-0Triisopropylsilanethiol156275-96-6tri(propan-2-yl)-sulfanylsilaneSilanethiol,1,1,1-tris(1-methylethyl)-MFCD00216593triisopropyl silanethioltriisopropyl-silanethioltriisopropylsilane thiolSilanethiol, 1,1,1-tris(1-methylethyl)-

Show more names

TriisopropylsilylthiolSKL291Triisopropylsilanethiol 97%Triisopropylsilanethiol 95%+trisopropylsiliconalkanethiolri(propan-2-yl)-sulfanylsilane1,1,1-Tris(1-methylethyl)silanethiol

SCHEMBL7141Triisopropylsilanethiol, 97%CS-0187703Silanethiol, tris(1-methylethyl)-C9H22SSiTriisopropylsitriisopropylsilyl thiolTIPS-SH

Database identifiers

CAS: 156275-96-6
PubChem CID: 3435097
DTXSID: DTXSID80392455
EC Number: 683-644-0
Nikkaji: J1.169.587F

Properties

Computed structural properties

Topological polar surface area: 1 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 97

Physicochemical properties

Boiling point: 70 · 70-75 °C2 mm Hg(lit.)
Density: 0.887 g/mL · 0.887 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.479(lit.)
Flash point: 171 °F · 171 °F
storage temp.: 2 · 2-8°C, stored under nitrogen
solubility: Soluble in most organic solvents.
form: liquid
pka: 9.86 · 9.86±0.10(Predicted)
Appearance: Colorless to light yellow Liquid
InChI: InChI=1S/C9H22SSi/c1-7(2)11(10,8(3)4)9(5)6/h7-10H,1-6H3
InChIKey: CPKHFNMJTBLKLK-UHFFFAOYSA-N
SMILES: [Si](C(C)C)(C(C)C)(C(C)C)S
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
RIDADR: 3334 · UN 3334
WGK Germany: 3 · 3
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Excepted Quantities: Non-Hazardous

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
ridadr: UN 3334
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Excepted Quantities: Non-Hazardous
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 1 item

UsesTriisopropylsilanethiol 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.