CAS 89343-06-6 (Triisopropylsilyl)acetylene (HCID 2734682)

Names & identifiers

Preferred name: (Triisopropylsilyl)acetylene
IUPAC: ethynyl-tri(propan-2-yl)silane
English name: (Triisopropylsilyl)acetylene
Molecular formula: C11H22Si
Molecular weight: 182.38

Names & synonyms

(Triisopropylsilyl)acetylene89343-06-6DTXSID30370445RefChem:408562DTXCID60321480629-580-9EthynyltriisopropylsilaneTriisopropylsilylacetyleneethynyltris(propan-2-yl)silaneethynyl-tri(propan-2-yl)silaneMFCD00075452Silane, ethynyltris(1-methylethyl)-

Show more names

TIPS ACETYLENE(Triisopropylsilyl)acetylene,97%DK423DKSI047DKFELEX0266JACS-89343-06-6Triisopropylsilylethyne

C11H22SiS18000ethynyl(triisopropyl)silaneethynyltri(isopropyl)silaneTIPS-acetyleneTriisopropylacetylenetriisopropylsilylacetylenethynyltriisopropyl-silane

Database identifiers

CAS: 89343-06-6
PubChem CID: 2734682
DTXSID: DTXSID30370445
UNII: DWX24P8A9S
EC Number: 629-580-9
Nikkaji: J890.896F

Properties

Computed structural properties

Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 4
Heavy atoms: 12
Formal charge: 0
Complexity: 159

Physicochemical properties

Melting point: 50 · 50-51 °C
Boiling point: 50 · 50-52 °C/0.6 mmHg (lit.)
Density: 0.813 g/mL · 0.813 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.4527(lit.)
Flash point: 133 °F · 133 °F
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: Miscible with organic solvents.
form: liquid
color: Clear, colourless
Specific Gravity: 0.813 · 0.813
Hydrolytic Sensitivity: 4 · 4: no reaction with water under neutral conditions
BRN: 3536241 · 3536241
InChI: InChI=1S/C11H22Si/c1-8-12(9(2)3,10(4)5)11(6)7/h1,9-11H,2-7H3
InChIKey: KZGWPHUWNWRTEP-UHFFFAOYSA-N
SMILES: [Si](C#C)(C(C)C)(C(C)C)C(C)C
CAS DataBase Reference: 89343 · 89343-06-6(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Warning
Hazard statements: 226 · H226-H315-H319-H335
Precautionary statements: 210 · P210-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 · 26-36/37/39-37/39
RIDADR: 1993 · UN 1993 3/PG 3
WGK Germany: 3 · 3
TSCA: N
HazardClass: 3.2 · 3.2
PackingGroup: III
HS Code: 29319090 · 29319090
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Flam · Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
REACH Registrations: Active
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (98.1%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 25-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/32819

Hazard Classes and CategoriesFlam. Liq. 3 (98.1%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: N
ridadr: UN 1993 3/PG 3
hs_code: 29319090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xi
safety_code: 26-36/37/39-37/39
hazard_class: 3.2
Storage Class: 3 - Flammable liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H226-H315-H319-H335
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
Precautionary statements: P210-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

Uses(Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes.

Uses(Triisopropylsilyl)acetylene (TIPS-acetylene) is an easily handled and inexpensive monoprotected acetylene used as an attractive substitute for trimethylsilylacetylene (TMSacetylene). The bulkier silyl protecting group of TIPS-acetylene provides stability in a wider range of reaction conditions than TMS-acetylene. Its higher boiling point also provides better handling and safety than TMS-acetylene (bp 87–88°C at 12 hPa (9 mmHg)). The general utility of TIPS-acetylene is often highlighted in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc.

General DescriptionAsymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds in the presence of a cobalt/Duphos catalyst is reported. A Sonogashira coupling reaction between 1-bromo-3-iodo-5-tertbutylbenzene and (triisopropylsilyl)acetylene is reported.