ChemicalBook Product Catalog Chemical Reagents Organic reagents Silane Bis(trimethylsilyl)acetylene

Bis(trimethylsilyl)acetylene

Product NameBis(trimethylsilyl)acetylene
CAS14630-40-1
MFC8H18Si2
MW170.4
EINECS238-671-9
MOL File14630-40-1.mol

Chemical Properties

Melting point	26 °C (79 °F; 299 K)
Boiling point	134.6 ± 8.0 °C (274.3 ± 14.4 °F; 407.8 ± 8.0 K)
Density	0.791 g/cm3
refractive index	n 20/D 1.427 (lit.)
Flash point	2 °C
storage temp.	2-8°C
solubility	soluble in Chloroform, Methanol
form	liquid
color	Colorless to white
Specific Gravity	0.770
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

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

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

Bis(trimethylsilyl)acetylene Supplier

Bis(trimethylsilyl)acetylene manufacturers

Related Product Information