(TRIETHYLSILYL)ACETYLENE Chemical Properties

Melting point:

95-97 °C(Solv: chloroform (67-66-3); hexane (110-54-3))

Boiling point:

136 °C

Density 

0.783 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.433(lit.)

Flash point:

63 °F

storage temp. 

Flammables area

form 

liquid

Specific Gravity

0.783

color 

colorless

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

BRN 

1743814

InChI

InChI=1S/C8H16Si/c1-5-9(6-2,7-3)8-4/h1H,6-8H2,2-4H3

InChIKey

FWSPXZXVNVQHIF-UHFFFAOYSA-N

SMILES

[Si](CC)(CC)(CC)C#C

CAS DataBase Reference

1777-03-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36/37/39

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

TSCA 

No

HazardClass 

3

PackingGroup 

II

HS Code 

29319090

Storage Class

3 - Flammable liquids

Hazard Classifications

Flam. Liq. 2

MSDS

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

(TRIETHYLSILYL)ACETYLENE Usage And Synthesis

Chemical Properties

Clear colorless to faintly yellow liquid

Uses

(Triethylsilyl)acetylene may be used in the synthesis of triethylsilylethynyl anthradithiophenes, such as :

• 2,8-dimethyl-5,11-bis(triethylsilylethynyl)ADT (ADT= anthradithiophene)
• 2,8-diethyl-5,11-bis(triethylsilylethynyl)ADT
• 2,8-dipropyl-5,11-bis(triethylsilylethynyl)ADT

General Description

(Triethylsilyl)acetylene, a bulky trialkylsilyl-protected alkyne, undergoes Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to yield synthetically useful unsymmetrical diynes. Rhodium-catalyzed dimerization of (triethylsilyl)acetylene has been reported.

Synthesis

CN201610096292.2 provides a method for synthesizing triethylsilylacetylene with readily available raw materials, a simple synthesis process, good controllability and good repeatability. The object of the present invention can be realized by the following technical solution: a synthesis method of triethylsilylacetylene, which is based on triethyl halosilane and acetylene metallization as raw materials, adding triethyl halosilane to an organic solution of acetylene metallization, heating and refluxing the reaction for 6-13 hours, then cooling to room temperature, adding ice water to quench the reaction, and then collecting the fraction at 42-48??C after decompression distillation, i.e., the production of Triethylsilylacetylene. The method specifically includes the following steps:

(1) preparing an organic solution of acetylene metallization, according to the molar ratio of acetylene metallization to triethyl halosilane of 1-1.3:1, slowly adding triethyl halosilane dropwise to the organic solution of acetylene metallization at 0-5??C under the protection of an inert gas;

(2) after the dropwise addition of triethylhalosilane, slowly increase the temperature to 60-100 ??, reflux reaction 6-10 hours, cooled to room temperature, add ice water to quench the reaction, extraction, retain the organic phase;

(3) The organic phase is washed and dried, then pumped and filtered, and then distilled under reduced pressure to collect the 42-48 ?? fraction, washed with water to remove inorganic salts can be.

(TRIETHYLSILYL)ACETYLENE(1777-03-3)Related Product Information

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• 1-(TRIMETHYLSILYL)-5-(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL
• 1,5-DI(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL