(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.

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(89343-06-6)Related Product Information

• TRIISOPROPYLSILANOL
• Triisopropyl[(trimethylsilyl)ethynyl]silane
• Triisopropylsilyl chloride
• Cyclohexane
• ETHYLENE
• 4-Aminobutyric acid
• Triisopropylsilane
• (TRIISOPROPYLSILYL)ACETYLENE
• Sodium 5-[(4-Amino-1-naphthyl)azo]-2-[4-[(2-hydroxy-1-naphthyl)azo]-2-sulfonatostyryl]benzenesulfonate
• 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