Bis(trimethylsilyl)acetylene Chemical Properties

Melting point:

21-24 °C(lit.)

Boiling point:

136-137 °C(lit.)

Density 

0.752 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.427(lit.)

Flash point:

29 °C

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Methanol

form 

liquid

Specific Gravity

0.770

color 

colorless

Water Solubility 

MAY DECOMPOSE

Hydrolytic Sensitivity

2: reacts with aqueous acid

BRN 

906870

InChI

1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3

InChIKey

ZDWYFWIBTZJGOR-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

14630-40-1(CAS DataBase Reference)

NIST Chemistry Reference

Silane, 1,2-ethynediylbis[trimethyl-(14630-40-1)

EPA Substance Registry System

Silane, 1,2-ethynediylbis[trimethyl- (14630-40-1)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38-10

Safety Statements 

16-26-36

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

F 

10

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

III

HS Code 

29310095

Storage Class

3 - Flammable liquids

Hazard Classifications

Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:Bis(trimethylsilyl)acetylene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Bis(trimethylsilyl)acetylene Usage And Synthesis

Chemical Properties

clear colorless liquid after melting

Uses

In the presence of CpCo(CO)2 (cat. no. 245259), undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.1

Uses

BTMSA is used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). Bis(trimethylsilyl)acetylene is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes, Permethyltitanocene-bis(trimethylsilyl)acetylene, is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]).

General Description

Bis(trimethylsilyl)acetylene (BTMSA) participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1,5-hexadiynes in the presence of CpCo(CO)₂ (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)?). TiCl₄-Et₂AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

Synthesis

Di(trimethylmethylsilyl)acetylene can be synthesized by the following steps:

1 With acetylene dimetallic salt and trimethyl halosilane as raw materials, acetylene dimetallic salt and trimethyl halosilane molar mass ratio of 1:2.0~1:2.2, first suspended in toluene, dropwise addition of trimethyl halosilane, dropwise addition, warming up to 50~60 ?? C reaction for 2 hours, in which the acetylene Dimetallic salt is disodium acetylene or dilithium acetylene;

2 Terminate the reaction with water, after extraction, drying, concentration under reduced pressure, distillation under reduced pressure, to obtain bis(trimethylsilyl)acetylene with purity of more than 99% and yield of more than 90%.

Purification Methods

Dissolve it in pet ether and wash it with ice-cold dilute HCl. The pet ether extract is dried (MgSO4), evaporated and fractionated at 760mm. [Walton & Waugh J Organomet Chem 37 45 1972, Beilstein 4 IV 3950.]

Bis(trimethylsilyl)acetylene(14630-40-1)Related Product Information

• Bis(trimethylsilyl)sulfate
• BIS(TRIMETHYLSILYLMETHYL)AMINE
• BIS(TRIMETHYLSILYLMETHYL)DICHLOROSILANE
• BIS(PHENYLETHYNYL)DIMETHYLSILANE
• 1,4-BIS(TRIMETHYLSILYL)-1,3-BUTADIYNE
• BIS(DIETHYLAMINO)DIMETHYLSILANE
• bis(4-broMophenyl)-diphenyl-silane
• bis(4-broMophenyl)diMethylsilane
• BIS(TRICHLOROSILYLETHYL)BENZENE,TECH-95
• BIS(METHYLDIETHOXYSILYLPROPYL)AMINE
• Bis(trimethylsilyl)methane
• Tetramethylsilane
• Bis(trimethylsilyl)acetylene
• Trimethylsilylacetylene
• (BIS(TRIMETHYLSILYL)ACETYLENE)(HEXAFLUO&,(bis(trimethylsilyl)acetylene)(hexafluoro-acetyla
• (TRIMETHYLSILYL)ACETYLENE-13C2
• [BIS(TRIMETHYLSILYL)ACETYLENE](HEXAFLUOROACETYLACETONATO)COPPER(I)
• Bis(trimethylsilyl)acetylene-bis(cyclopentadienyl)(pyridine)zirconium,Bis(cyclopentadienyl)zirconium bis(trimethylsilyl)acetylene pyridine complex