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1066-54-2

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Identification

Name
Trimethylsilylacetylene
CAS
1066-54-2
Synonyms
ETHINYLTRIMETHYLSILANE
ETHYNYLTRIMETHYLSILANE
TMSA
TMS ACETYLENE
TRIMETHYLSILYLACETYLENE
(Trimethylsilyl)ethyne
1-(Trimethylsilyl)acetylene
1-Trimethylsilylethyne
Acetylene, trimethylsilyl-
Ethyne,-trimethylsilyl
ethynyltrimethyl-silan
Silane, ethynyltrimethyl-
Silane, trimethyl-, ethynyl-
Silane,ethynyltrimethyl-
Trimethylethynylsilane
(Thrimethylsilyl)acetylene
Ethynyltrimethylsilane~TMS acetylene
ETHYNYLTRIMETHYLSILANE, WACKER-QUALITY
(TRIMETHYLSILYL)ACETYLENE, 98+%
Trimethylsilylacetylene,min.97%
EINECS(EC#)
213-919-9
Molecular Formula
C5H10Si
MDL Number
MFCD00008569
Molecular Weight
98.22
MOL File
1066-54-2.mol

Chemical Properties

Appearance
CLEAR COLORLESS LIQUID
Melting point 
>0°C
mp 
>0°C
Boiling point 
53 °C(lit.)

bp 
53 °C(lit.)

density 
0.695 g/mL at 25 °C(lit.)

vapor pressure 
4.18 psi ( 20 °C)

refractive index 
n20/D 1.388(lit.)

Fp 
<−30 °F

storage temp. 
2-8°C

solubility 
Miscible with organic solvents.
form 
liquid
Specific Gravity
0.695
color 
colorless
Water Solubility 
reacts
Hydrolytic Sensitivity
4: no reaction with water under neutral conditions
Detection Methods
GC,NMR
BRN 
906752
InChIKey
CWMFRHBXRUITQE-UHFFFAOYSA-N
CAS DataBase Reference
1066-54-2(CAS DataBase Reference)
NIST Chemistry Reference
(Trimethylsilyl)acetylene(1066-54-2)
EPA Substance Registry System
1066-54-2(EPA Substance)

Safety Data

Hazard Codes 
F,Xi
Risk Statements 
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
RIDADR 
UN 1993 3/PG 2

WGK Germany 
-

Hazard Note 
Flammable/Irritant
TSCA 
T
HazardClass 
3
PackingGroup 
II
HS Code 
29310095

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Questions And Answer

Silican-protected group
Trimethylsilylacetylene is a silican-protected group, also known as trimethylethynylsilane, trimethylethynyl silicon and ethynyltrimethylsilane. It is a colorless transparent liquid at room temperature. It could be used to synthesize parazole by the addition of 1,3-bipolar ring of acetylene diazide. It is also the substrate of nickel catalyzed reaction and benzonitrile coupling reaction.
Application
  • Common intermediate for asymmetric synthesis
  • Silica reagent

Hazard Information

Chemical Properties
CLEAR COLORLESS LIQUID
Physical properties
bp 53 °C; d 0.695 g cm?3.
Uses
Ethynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes
Uses
Trimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.
Purification Methods
Distil it through an efficient column. The IR has bands at max 2041 (CC) and 3289 (C-H) cm-1. [Kr.hnke & Goss Chem Ber 92 30 1959, Beilstein 4 IV 3937.]

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