Cas no 18387-63-8 ((3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane)

(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane is a silyl-protected chloroalkyne compound widely used in synthetic organic chemistry as a versatile building block. Its key advantages include stability under various reaction conditions and compatibility with cross-coupling and nucleophilic substitution reactions. The trimethylsilyl (TMS) group enhances handling safety by reducing volatility while allowing selective deprotection when needed. The chloroalkyne moiety serves as a reactive handle for further functionalization, enabling the synthesis of complex molecular architectures. This compound is particularly valuable in medicinal chemistry and materials science for constructing alkynyl-substituted intermediates. Its robust shelf stability and predictable reactivity make it a reliable reagent for controlled C–C bond-forming transformations.
(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane structure
18387-63-8 structure
Product Name:(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane
CAS No:18387-63-8
MF:C8H15ClSi
MW:174.743202447891
MDL:MFCD25977266
CID:1377945
PubChem ID:11217537
Update Time:2025-06-07

(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane Chemical and Physical Properties

Names and Identifiers

    • Silane, (3-chloro-3-methyl-1-butynyl)trimethyl-
    • 3-chloro-3-methyl-1-(trimethylsilyl)-1-butyne
    • (3-chloro-3-methylbut-1-ynyl)trimethylsilane
    • 1-trimethylsilyl-3-methyl-3-chlorobut-1-yne
    • 3-chloro-3-methyl-1-trimethylsilyl-1-butyne
    • 3-methyl-1-(trimethylsilyl)-1-butyne
    • Silane, (3-chloro-3-methyl-1-butyn-1-yl)trimethyl-
    • (3-chloro-3-methylbut-1-yn-1-yl)trimethylsilane
    • Silane, (3-chloro-3-Methyl-1-butyn-1-yl)triMethyl-3
    • WSSUODWANZMVMQ-UHFFFAOYSA-N
    • 4-trimethylsilyl-2-methyl-2-chloro-3-butyne
    • (3-Chloro-3-methyl-1-butynyl)trimethylsilane
    • Silane,(3-chloro-3-Methyl-1-butyn-1-yl)triMethyl-
    • DB-304513
    • SCHEMBL352538
    • (3-chloro-3-methylbut-1-ynyl)-trimethylsilane
    • 18387-63-8
    • CS-13141
    • CS-M2010
    • AKOS030239250
    • (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane
    • MDL: MFCD25977266
    • Inchi: 1S/C8H15ClSi/c1-8(2,9)6-7-10(3,4)5/h1-5H3
    • InChI Key: WSSUODWANZMVMQ-UHFFFAOYSA-N
    • SMILES: ClC(C)(C)C#C[Si](C)(C)C

Computed Properties

  • Exact Mass: 174.06300
  • Monoisotopic Mass: 174.0631547g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 174
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 0

Experimental Properties

  • Density: 0.9±0.1 g/cm3
  • Boiling Point: 171.5±13.0 °C at 760 mmHg
  • Flash Point: 52.9±14.6 °C
  • PSA: 0.00000
  • LogP: 2.88460
  • Vapor Pressure: 1.9±0.3 mmHg at 25°C

(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane Security Information

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Additional information on (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane

Introduction to (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane (CAS No. 18387-63-8)

(3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane, identified by its CAS number 18387-63-8, is a specialized organosilicon compound that has garnered significant attention in the field of synthetic chemistry and pharmaceutical research. This compound, characterized by its unique structure, exhibits a versatile reactivity that makes it a valuable intermediate in the synthesis of complex molecules. Its molecular formula, C?H??ClSi, reflects a combination of carbon, hydrogen, chlorine, and silicon atoms, which contribute to its distinct chemical properties.

The utility of (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane stems from its ability to participate in various organic transformations, including nucleophilic substitution reactions, cross-coupling reactions, and silane-mediated reactions. These reactions are fundamental in the construction of carbon-carbon and carbon-heteroatom bonds, which are essential for the development of novel pharmaceuticals and agrochemicals. The presence of a terminal alkyne group and a chlorosilane moiety provides multiple sites for functionalization, making it a versatile building block in synthetic chemistry.

In recent years, there has been a surge in research focused on the development of novel methodologies for constructing complex molecular architectures. Among these methodologies, organosilicon compounds have emerged as pivotal reagents due to their ability to facilitate efficient and selective transformations. (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane has been particularly studied for its role in facilitating the synthesis of biologically active compounds. For instance, its application in the preparation of substituted alkenes and alkynes has been explored as a means to generate intermediates for drug discovery.

One of the most notable applications of (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane is in the synthesis of heterocyclic compounds, which are prevalent in many pharmaceuticals. Researchers have leveraged its reactivity to introduce functional groups at specific positions within heterocyclic frameworks, thereby modulating their biological activity. This approach has been particularly useful in the development of antiviral and anticancer agents. The compound's ability to undergo regioselective reactions ensures that functionalization occurs at desired sites, minimizing unwanted side products and improving overall yields.

The silane moiety in (3-Chloro-3-methylbut-1-yn-1-yl)trimethylsilane also contributes to its utility as a protecting group or a leaving group in various synthetic protocols. Silanes can be selectively removed under specific conditions, allowing for precise control over reaction outcomes. This feature is particularly valuable in multi-step syntheses where sequential functionalization is required. The stability of the trimethylsilyl (TMS) group under harsh conditions makes it an ideal choice for protecting sensitive functional groups during synthetic transformations.

Recent advances in catalytic systems have further expanded the applications of organosilicon compounds like (3-Chloro-3-methylbut-1-yn-1-ylltrimethylsilane. Transition metal-catalyzed reactions, such as palladium-catalyzed cross-coupling reactions, have enabled the efficient construction of complex molecular architectures from simpler precursors. These reactions often require specialized reagents to facilitate coupling between different organic fragments. The unique reactivity of (3-Chloro-3-methylbut-1-ylltrimethylsilane makes it an excellent candidate for such transformations, contributing to the rapid assembly of pharmacologically relevant molecules.

The synthesis of complex natural products has also benefited from the use of (3-Chloro-3-methylbut-ylltrimethylsilane. Natural products often feature intricate stereochemical arrangements that are challenging to replicate through traditional synthetic methods. Organosilicon compounds provide access to novel synthetic pathways that can overcome these challenges by enabling selective functionalization and stereoselective transformations. This has been particularly useful in the total synthesis of complex biomolecules with significant therapeutic potential.

In conclusion, (3-Chloro--methylbut-ylltrimethylsilane (CAS No. 18387--63--8) is a multifaceted organosilicon compound with broad applications in synthetic chemistry and pharmaceutical research. Its unique structure and reactivity make it an invaluable tool for constructing complex molecular architectures, particularly in the development of biologically active compounds. As research continues to evolve, it is likely that new applications for this compound will emerge, further solidifying its importance in the chemical sciences.

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