(Triisopropylsilyl)acetylene
- Product Name
- (Triisopropylsilyl)acetylene
- CAS No.
- 89343-06-6
- Chemical Name
- (Triisopropylsilyl)acetylene
- Synonyms
- ETHYNYLTRIISOPROPYLSILANE;TIPS ACETYLENE;Triisopropylacetylene;ethynyltris(propan-2-yl)silane;(Triisopropylsilyl)acetylene,97%;DK423;DKSI047;DKFELEX0266;JACS-89343-06-6;Triisopropylsilylethyne
- CBNumber
- CB0416001
- Molecular Formula
- C11H22Si
- Formula Weight
- 182.38
- MOL File
- 89343-06-6.mol
(Triisopropylsilyl)acetylene Property
- 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.)
- Flash point:
- 133 °F
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Miscible with organic solvents.
- form
- liquid
- Specific Gravity
- 0.813
- color
- Clear, colourless
- Hydrolytic Sensitivity
- 4: no reaction with water under neutral conditions
- BRN
- 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
- 89343-06-6(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39-37/39
- RIDADR
- UN 1993 3/PG 3
- WGK Germany
- 3
- TSCA
- N
- HazardClass
- 3.2
- PackingGroup
- III
- HS Code
- 29319090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H226Flammable liquid and vapour
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 360031
- Product name
- (Triisopropylsilyl)acetylene
- Purity
- 97%
- Packaging
- 5g
- Price
- $110
- Updated
- 2025/07/31
- Product number
- 360031
- Product name
- (Triisopropylsilyl)acetylene
- Purity
- 97%
- Packaging
- 25g
- Price
- $314
- Updated
- 2025/07/31
- Product number
- T1683
- Product name
- Triisopropylsilylacetylene
- Purity
- >95.0%(GC)
- Packaging
- 5mL
- Price
- $76
- Updated
- 2025/07/31
- Product number
- T1683
- Product name
- Triisopropylsilylacetylene
- Purity
- >95.0%(GC)
- Packaging
- 25mL
- Price
- $265
- Updated
- 2025/07/31
- Product number
- T795413
- Product name
- Triisopropylsilylacetylene
- Packaging
- 5g
- Price
- $75
- Updated
- 2021/12/16
(Triisopropylsilyl)acetylene Chemical Properties,Usage,Production
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 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.
Application
(Triisopropylsilyl)acetylene is often used in palladium-catalyzed Sonogashira coupling reactions to react with aryl halides to generate terminal alkynes. This reaction has good functional group compatibility and is suitable for later modification of drug molecules. It can be used for rhodium-catalyzed asymmetric alkynylation of α,β-unsaturated ketones to generate products with high stereoselectivity.
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.
storage
(Triisopropylsilyl)acetylene (Ethynyltriisopropylsilane) is stable to air and moisture, incompatible with strong acids, bases, or oxidants, and flammable vapor and liquid. Skin/eye contact and inhalation should be avoided.
(Triisopropylsilyl)acetylene Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from (Triisopropylsilyl)acetylene manufacturers
- Product
- (Triisopropylsilyl)acetylene 89343-06-6
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-07-08
- Product
- Triisopropylsilylacetylene 89343-06-6
- Price
- US $3.00-9.00/KG
- Min. Order
- 0.1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2025-06-27
- Product
- (TRIISOPROPYLSILYL)ACETYLENE 89343-06-6
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-29