| Identification | More | [Name]
(TRIISOPROPYLSILYL)ACETYLENE | [CAS]
89343-06-6 | [Synonyms]
ETHYNYLTRIISOPROPYLSILANE
(TRIISOPROPYLSILYL)ACETYLENE | [EINECS(EC#)]
629-580-9 | [Molecular Formula]
C11H22Si | [MDL Number]
MFCD00075452 | [Molecular Weight]
182.38 | [MOL File]
89343-06-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless liquid | [Melting point ]
50-51 °C | [Boiling point ]
50-52 °C/0.6 mmHg (lit.) | [density ]
0.813 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4527(lit.)
| [Fp ]
133 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Miscible with organic solvents. | [Specific Gravity]
0.813 | [Hydrolytic Sensitivity]
4: no reaction with water under neutral conditions | [BRN ]
3536241 | [InChIKey]
KZGWPHUWNWRTEP-UHFFFAOYSA-N | [CAS DataBase Reference]
89343-06-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [TSCA ]
N | [HazardClass ]
3.2 | [PackingGroup ]
III | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless liquid | [Physical properties]
colorless clear liquid; bp 50–52 °C at 0.8 hPa
(0.6 mmHg), flash point 56 °C (closed cup); d = 0.813. | [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 Description]
Asymmetric 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. |
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