(Triisopropylsilyl)acetylene Chemical Properties

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 Information

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

(Triisopropylsilyl)acetylene Usage And Synthesis

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.

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(89343-06-6)Related Product Information

• Triisopropylsilane
• Triisopropylsilyl chloride
• Cyclohexane
• ETHYLENE
• 4-Aminobutyric acid
• Triisopropyl[(trimethylsilyl)ethynyl]silane
• TRIISOPROPYLSILANOL
• (TRIISOPROPYLSILYL)ACETYLENE
• Triisopropylsilane
• 1-TRIISOPROPYLSILYL-1-PROPYNE
• [(Triisopropylsilyl)acetylene]sulfur pentafluoride
• (Bromoethynyl)triisopropylsilane
• 3-TRIISOPROPYLSILYL-2-PROPYN-1-OL
• 1-(TRIMETHYLSILYL)-5-(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL
• 1,5-DI(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL
• 1-Nitro-2-(triisopropylsilyl)acetylene
• 4-ACETOXY-3-[(TRIISOPROPYLSILANYL)ETHYNYL]-BENZOIC ACID METHYL ESTER
• 3-BROMO-1-(TRIISOPROPYLSILYL)-1-PROPYNE