ChemicalBook CAS DataBase List 14630-40-1

14630-40-1

Name	Bis(trimethylsilyl)acetylene
CAS	14630-40-1
EINECS(EC#)	238-671-9
Molecular Formula	C8H18Si2
MDL Number	MFCD00008276
Molecular Weight	170.4
MOL File	14630-40-1.mol

Synonyms

1,2-BIS-TRIMETHYLSILANYL-ETHYNE BIS(TRIMETHYLSILYL)ACETYLENE BSTMA BTMSA TIMTEC-BB SBB008997 1,2-Bis(trimethylsilyl)acetylene 1,2-Bis(trimethylsilyl)ethyne 1,2-ethynediylbis[trimethyl-silan 1,2-ethynediylbis[trimethyl-Silane 2,5-Disilahex-3-yne, 2,2,5,5-tetramethyl- Acetylene, bis(trimethylsilyl)- Bis(trimethylsilyl)ethyne Silane, 1,2-ethynediylbis*trimethyl- Trimethyl[(trimethylsilyl)ethynyl]silane Bis(trimethylsilyl)acetylene(BTMSA) Bis(trimethylsilyl)acetylene,min.97% Ethynylbistrimethylsilanel 5-Fluoro-2-methoxy-phenylamine Bis(trimethylsilyl)acetylene, min. 97%

Chemical Properties

Appearance	clear colorless liquid after melting
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.)
Fp	29 °C
storage temp.	0-6°C
solubility	soluble in Chloroform, Methanol
form	liquid
color	colorless
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)
Storage Precautions	Store under nitrogen
EPA Substance Registry System	14630-40-1(EPA Substance)

Safety Data

Symbol(GHS)	GHS02,GHS07
Signal word	Danger
Hazard statements	H225-H315-H319-H335
Precautionary statements	P210-P302+P352-P305+P351+P338
Hazard Codes	F,Xi
Risk Statements	R11:Highly Flammable. R36/37/38:Irritating to eyes, respiratory system and skin . less more
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 . less more
RIDADR	UN 1993 3/PG 2
WGK Germany	3
F	10
TSCA	Yes
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

Raw materials And Preparation Products

Hazard Information

Chemical Properties

clear colorless liquid after melting

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]).

Uses

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

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 sus

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.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

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