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Bis(trimethylsilyl)acetylene, also known as BTMSA, is a versatile chemical compound that participates as a nucleophile in Friedel-Crafts type acylations and alkylations. It is characterized by a center of inversion present on its triple bond and is a clear colorless liquid after melting. BTMSA is used as a starting reagent in the synthesis of various organic compounds and as a ligand in coordination complexes.

14630-40-1

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14630-40-1 Usage

Uses

1. Used in Organic Synthesis:
Bis(trimethylsilyl)acetylene is used as a starting reagent for the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne and (β-diketanato)Ag(BTMSA).
2. Used in Coordination Complexes:
BTMSA acts as a ligand that binds to a central metal ion, such as 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, such as 3-Penten-1-yne [P227430].
3. Used in Cycloaddition Reactions:
In the presence of CpCo(CO)2 (cat. no. 245259), BTMSA undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.
4. Used in Rhodium-Catalyzed Addition Reactions:
BTMSA undergoes rhodium catalyzed addition reactions with diarylacetylenes, which can lead to the formation of various organic compounds.
5. Used in Diels-Alder Reactions:
The TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported, showcasing its utility in this type of reaction.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 14630-40-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,3 and 0 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 14630-40:
(7*1)+(6*4)+(5*6)+(4*3)+(3*0)+(2*4)+(1*0)=81
81 % 10 = 1
So 14630-40-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3

14630-40-1 Well-known Company Product Price

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  • TCI America

  • (B1090)  Bis(trimethylsilyl)acetylene  >97.0%(GC)

  • 14630-40-1

  • 5g

  • 290.00CNY

  • Detail
  • TCI America

  • (B1090)  Bis(trimethylsilyl)acetylene  >97.0%(GC)

  • 14630-40-1

  • 25g

  • 1,130.00CNY

  • Detail
  • Alfa Aesar

  • (A11960)  Bis(trimethylsilyl)acetylene, 99%   

  • 14630-40-1

  • 10g

  • 505.0CNY

  • Detail
  • Alfa Aesar

  • (A11960)  Bis(trimethylsilyl)acetylene, 99%   

  • 14630-40-1

  • 50g

  • 1970.0CNY

  • Detail
  • Alfa Aesar

  • (A11960)  Bis(trimethylsilyl)acetylene, 99%   

  • 14630-40-1

  • 250g

  • 7891.0CNY

  • Detail
  • Aldrich

  • (187437)  Bis(trimethylsilyl)acetylene  99%

  • 14630-40-1

  • 187437-10G

  • 538.20CNY

  • Detail
  • Aldrich

  • (187437)  Bis(trimethylsilyl)acetylene  99%

  • 14630-40-1

  • 187437-50G

  • 1,897.74CNY

  • Detail

14630-40-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Bis(trimethylsilyl)acetylene

1.2 Other means of identification

Product number -
Other names Silane, 1,2-ethynediylbis[trimethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14630-40-1 SDS

14630-40-1Relevant articles and documents

Mechanism-based design of labile precursors for chromium(i) chemistry

Akturk, Eser S.,Yap, Glenn P. A.,Theopold, Klaus H.

, p. 15402 - 15405 (2015)

Dinitrogen complexes of the type TpR,RCr-N2-CrTpR,R are not the most labile precursors for Cr(i) chemistry, as they are sterically protected from obligatory associative ligand substitution. A mononuclear alkyne complex-TptBu,MeCr(η2-C2(SiMe3)2)-proved to be much more reactive.

REACTION OF GERMYLENE WITH THIOKETENES: SYNTHESIS OF ALKYLIDENEDIGERMATHIETANES

Ando, Wataru,Tsumuraya, Takeshi,Goto, Midori

, p. 5105 - 5108 (1986)

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

Fitzmaurice, Neil J.,Jackson, W. Roy,Perlmutter, Patrick

, p. 375 - 382 (1985)

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

Courtemanche, Marc-André,Transue, Wesley J.,Cummins, Christopher C.

, p. 16220 - 16223 (2016)

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

Sekiguchi,Matsuo,Tanaka,Watanabe,Nakamoto

, p. 1109 - 1115 (2004)

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.

Et2Zn-mediated stoichiometric C(sp)-H silylation of 1-alkynes and chlorosilanes

Huang, Pan,Xu, Dawen,Reich, Robert M.,Kaiser, Felix,Liu, Boping,Kühn, Fritz E.

supporting information, p. 1574 - 1577 (2019/05/17)

A first example of an Et2Zn mediated silylation of 1-aklynes is reported. A series of functional groups are tolerated in this reaction. Mechanistic studies support Zn alkynilides as intermediates in the reaction. This reaction protocol provides a practical method for the preparation of alkynylsilanes and expands the application of organometallic zinc in organic synthesis.

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

Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika

supporting information, p. 1098 - 1102 (2019/05/16)

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.

Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes

Puthanveedu, Mahesh,Polychronidou, Vasiliki,Antonchick, Andrey P.

, p. 3407 - 3411 (2019/05/10)

A metal-free, regioselective C-H functionalization of heteroaromatic N-oxides has been developed. The method enables the synthesis of various benzylated and alkynylated N-heterocycles in a transition-metal-free manner employing organosilanes as coupling partners. The unanticipated reactivity has been exploited for the synthesis of a number of symmetrical disubstituted acetylenes from ethynyltrimethylsilane via carbon-silicon bond metathesis.

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

Flynn, Matthew T.,Blair, Victoria L.,Andrews, Philip C.

supporting information, p. 1225 - 1228 (2018/04/30)

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.

Facile access to tuneable Schwartz's reagents: Oxidative addition products from the reaction of amide N-H bonds with reduced zirconocene complexes

Haehnel, Martin,Yim, Jacky C.-H.,Schafer, Laurel L.,Rosenthal, Uwe

supporting information, p. 11415 - 11419 (2013/11/06)

On the tracks of Schwartz's reagent: Two zirconocene hydrido amidate complexes are synthesized by formal oxidative addition of amide N-H bonds to reduced zirconocene fragments. Insertion reactions with alkenes show a different behavior than Schwartz's reagent by forming branched insertion products. The insertion product and the hydrido complex are characterized by X-ray analysis. Copyright

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