14630-40-1

Basic information

• Product Name: Bis(trimethylsilyl)acetylene
• Synonyms: 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-
• CAS NO: 14630-40-1
• Molecular Formula: C₈H₁₈Si₂
• Molecular Weight: 170.4
• EINECS: 238-671-9
• Product Categories: Industrial/Fine Chemicals;Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;organosilicon compounds;Alkynes;Building Blocks;Chemical Synthesis;Internal;Organic Building Blocks
• Mol File: 14630-40-1.mol
• Article Data: 41

Chemical Properties

• Melting Point: 21-24 °C(lit.)
• Boiling Point: 136-137 °C(lit.)
• Flash Point: 29 °C
• Appearance: colorless/liquid
• Density: 0.752 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.9mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: MAY DECOMPOSE
• BRN: 906870
• CAS DataBase Reference: Bis(trimethylsilyl)acetylene(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(trimethylsilyl)acetylene(14630-40-1)
• EPA Substance Registry System: Bis(trimethylsilyl)acetylene(14630-40-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38-10
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 14630-40-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid after melting

Uses

Different sources of media describe the Uses of 14630-40-1 differently. You can refer to the following data:
1. In the presence of CpCo(CO)2 (cat. no. 245259), undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.1
2. 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.

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.]

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

Upstream product

• 18038-55-6 1,2-bis-(trichlorosilyl)acetylene 
• 75-16-1 methylmagnesium bromide 
• 156-59-2 cis-1,2-Dichloroethylene 
• 75-77-4 chloro-trimethyl-silane 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 13915-90-7 trichlorovinyltrimethylsilane 
• 35802-68-7 β-chlorovinyltrimethylsilane 
• 109-92-2 ethyl vinyl ether 
• 62827-97-8 Bis(trimethylsilyl)thioketene 
• 76054-64-3 7,7-dimethyl-1,4,5,6-tetraphenyl-2,3-benzo-7-germanorbornadiene 
• 7727-37-9 nitrogen 
• 67-56-1 methanol 
• 70057-32-8 1-(trimethylsilylethynyl)-1,1-diphenyl-2,2,2-trimethyldisilane 
• 79-01-6 Trichloroethylene 

Downstream Products

• 5930-98-3 4-trimethylsilyl-3-butyn-2-one 
• 100-47-0 benzonitrile 
• 126386-46-7 3,4-Bis(trimethylsilyl)furan 
• 34452-56-7 trimethylsilyl p-tolylsulfonylacetylene 
• 18617-50-0 1-ethyl-2-pyridone-5-carboxylic acid 
• 160729-90-8 ethyl furo<2,3-b>pyridyne-5-carboxylate 
• 1743-61-9 1,4-dimethyl-4-vinylcyclohex-1-ene 
• 87226-80-0 1,2-bis(trimethylsilyl)-4-methylcyclohexa-1,4-diene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 74-86-2 acetylene 
• 4683-50-5 3-methoxycyclopent-2-enone 
• 121906-88-5 2,3-bis(trimethylsilyl)-4-methoxy-2,4-cyclopentadienone 
• 16469-62-8 pent-1-yn-3-one 

Relevant articles and documents

REACTION OF GERMYLENE WITH THIOKETENES: SYNTHESIS OF ALKYLIDENEDIGERMATHIETANES

In the reaction of dimethyl- or diphenylgermylene with di-tert-butyl-thioketene alkylidenedigermathietanes were obtained, probably via alkylidenegermathiiranes.The exact structure of alkylidenedigermathietane 2b was confirmed by X-ray crystal analysis.

THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS. XXXVI. REGIO- AND STEREO-CHEMICAL CONTROL IN THE NICKEL-CATALYSED HYDROCYANATION OF SILYLALKYNES

The regioselectivity of hydrocyanation of silylalkynes can be controlled by varying the size of the groups attached to silicon leading, for example, to efficient preparations of E-3-trialkylsilyl-2-alkyl-2-alkenenitriles.High yields of the silylalkene nitriles can be obtained by using either acetone cyanohydrin or hydrogen cyanide as reagents.

Phosphinidene Reactivity of a Transient Vanadium P≡N Complex

Toward the preparation of a coordination complex of the heterodiatomic molecule PN, P≡N-V(N[tBu]Ar)3 (1, Ar = 3,5-Me2C6H3), we report the use of ClPA (A = C14H10, anthracene) as a formal source of phosphorus(I) in its reaction with Na[NV(N[tBu]Ar)3] (Na[4]) to yield trimeric cyclo-triphosphane [PNV(N[tBu]Ar)3]3 (3) with a core composed exclusively of phosphorus and nitrogen. In the presence of NapS2 (peri-1,8-naphthalene disulfide), NapS2P-NV(N[tBu]Ar)3 (6) is instead generated in 80% yield, suggesting trapping of transient 1. Upon mild heating, 3 readily fragments into dimeric [PNV(N[tBu]Ar)3]2 (2), while in the presence of bis(trimethylsilyl)acetylene or cis-4-octene, the respective phosphirene (Ar[tBu]N)3VN-PC2(SiMe3)2 (7) or phosphirane (Ar[tBu]N)3VN-P(C8H16) (8) compounds are generated. Kinetic data were found to be consistent with unimolecular decay of 3, and [2+1]-cycloaddition with radical clocks ruled out a triplet intermediate, consistent with intermediate 1 reacting as a singlet phosphinidene. In addition, both 7 and 8 were shown to reversibly exchange cis-4-octene and bis(trimethylsilyl)acetylene, serving as formal sources of 1, a reactivity manifold traditionally reserved for transition metals.

Tetrasilyl-substituted cyclobutadiene dianion dilithium salt: Synthesis and structure

The reaction of tetrakis(trimethylsilyl)cyclobutadienylcyclopentadienyl cobalt complex (Me3Si)4C4CoCp with lithium metal in THF yielded the dilithium salt of cyclobutadiene dianion CBD 2- stabilized by four trimethylsilyl groups, Li+ 2[(Me3Si)4C4]2-. The bridged CBD2- dianion was also synthesized by a similar procedure starting from the bridged cobalt complex, which was prepared from the reaction of 2,2,5,5,8,8,11,11-octamethyl-2,5,8,11-tetrasilacyclododeca-1,6-diyne with CpCo(CO)2 in refluxing octane. The aromaticity of the CBD 2- is discussed on the basis of the structural characteristics and magnetic properties.

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

Metal Acetylide Elimination: The Key Step in the Cascade Decomposition and Transformation of Metalated Propargylamines

Metal acetylide elimination facilitates a novel one-pot cascade metalation and elimination/addition route to a series of unsymmetrical secondary amines from the reaction of secondary propargylamines with organometallic reagents. Spectroscopic evidence suggests a dimetalated amido intermediate rather than an allene.