Cas no 6651-36-1 (1-(Trimethylsiloxy)cyclohexene)

1-(Trimethylsiloxy)cyclohexene is a silyl enol ether derivative of cyclohexanone, commonly utilized as a versatile intermediate in organic synthesis. Its key advantage lies in its ability to act as a masked enolate equivalent, enabling controlled nucleophilic reactions under mild conditions. The trimethylsiloxy group enhances stability while facilitating regioselective functionalization, making it valuable for aldol condensations, Michael additions, and other C–C bond-forming processes. The compound’s moisture sensitivity necessitates handling under inert conditions, but its reactivity profile offers synthetic flexibility in constructing complex molecular frameworks. Its utility in protecting group strategies and as a precursor for further modifications underscores its importance in fine chemical and pharmaceutical applications.
1-(Trimethylsiloxy)cyclohexene structure
6651-36-1 structure
Product Name:1-(Trimethylsiloxy)cyclohexene
CAS No:6651-36-1
MF:C9H18OSi
MW:170.324123859406
MDL:MFCD00001541
CID:46933
PubChem ID:87577315
Update Time:2025-06-11

1-(Trimethylsiloxy)cyclohexene Chemical and Physical Properties

Names and Identifiers

    • (Cyclohex-1-en-1-yloxy)trimethylsilane
    • 1-(Trimethylsiloxy)cyclohexene
    • 1-Cyclohexenyloxytrimethylsilane
    • 1-Trimethylsilylcyclohexene
    • 1-(Trimethylsilyloxy)cyclohexene
    • (CYCLOHEXENYLOXY)TRIMETHYLSILANE
    • 1-Trimethylsilyloxycyclohexene
    • cyclohexen-1-yloxy(trimethyl)silane
    • (1-Cyclohexen-1-yloxy)trimethylsilane
    • AKOS005256829
    • A851804
    • T1556
    • FS-3856
    • 1-trimethylsiloxycyclohexene
    • EINECS 229-675-1
    • 1-trimethylsilyloxy-1-cyclohexene
    • 1-(Trimethylsilyloxy)-1-cyclohexene
    • 1-(trimethylsilyl-oxy)cyclohexene
    • D92487
    • cyclohexene, 1-[(trimethylsilyl)oxy]-
    • 1-trimethylsiloxy-cyclohexene
    • SCHEMBL817040
    • FT-0605885
    • 1-Trimethylsiloxy-1-cyclohexene
    • trimethylsiloxycyclohexene
    • Trimethylsilyloxy-1-Cyclohexene
    • 1-(Trimethylsiloxy)cyclohexene, 99%
    • InChI=1/C9H18OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h7H,4-6,8H2,1-3H
    • .alpha.-Trimethylsiloxycyclohexene
    • 6651-36-1
    • Cyclohexenyloxytrimethylsilane
    • (cyclohex-1-en-1-yloxy)(trimethyl)silane
    • CS-0204290
    • J-802002
    • MFCD00001541
    • NS00046734
    • ghl.PD_Mitscher_leg0.948
    • DTXSID7064441
    • S05075
    • Silane, (1-cyclohexen-1-yloxy)trimethyl-
    • Cyclohexanone enol trimethylsilyl ether
    • Cyclohexene, 1-((trimethylsilyl)oxy)-
    • BBL102330
    • STL556130
    • MDL: MFCD00001541
    • Inchi: 1S/C9H18OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h7H,4-6,8H2,1-3H3
    • InChI Key: SBEMOANGDSSPJY-UHFFFAOYSA-N
    • SMILES: [Si](C)(C)(C)OC1=CCCCC1
    • BRN: 1859394

Computed Properties

  • Exact Mass: 170.11300
  • Monoisotopic Mass: 170.113
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 155
  • 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
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 9.2A^2

Experimental Properties

  • Color/Form: Transparent yellow liquid
  • Density: 0.875?g/mL?at 25?°C(lit.)
  • Boiling Point: 165°C(lit.)
  • Flash Point: Fahrenheit: 105.8 ° f
    Celsius: 41 ° c
  • Refractive Index: n20/D 1.447(lit.)
  • Solubility: Not miscible or difficult to mix.
  • PSA: 9.23000
  • LogP: 3.29580
  • Sensitiveness: Moisture Sensitive

1-(Trimethylsiloxy)cyclohexene Security Information

  • Symbol: GHS02
  • Prompt:warning
  • Signal Word:Warning
  • Hazard Statement: H226
  • Warning Statement: P210-P233-P240-P241+P242+P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
  • Hazardous Material transportation number:UN 1993 3/PG 3
  • WGK Germany:3
  • Hazard Category Code: 10
  • Safety Instruction: S16
  • FLUKA BRAND F CODES:10-21
  • Hazardous Material Identification: F
  • HazardClass:3
  • PackingGroup:III
  • TSCA:Yes
  • Packing Group:III
  • Hazard Level:3
  • Safety Term:3
  • Packing Group:III
  • Risk Phrases:R10
  • Storage Condition:Store at 4°C,-4At ℃Store…Better

1-(Trimethylsiloxy)cyclohexene Customs Data

  • HS CODE:2931900090
  • Customs Data:

    China Customs Code:

    2931900090

    Overview:

    2931900090. Other organic-Inorganic compound. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:AB(Customs clearance form for Inbound Goods,Customs clearance form for outbound goods). MFN tariff:6.5%. general tariff:30.0%

    Summary:

    2931900090. other organo-inorganic compounds. VAT:17.0%. Tax rebate rate:13.0%. Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward). MFN tariff:6.5%. General tariff:30.0%

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1-(Trimethylsiloxy)cyclohexene Related Literature

Additional information on 1-(Trimethylsiloxy)cyclohexene

Introduction to 1-(Trimethylsiloxy)cyclohexene (CAS No. 6651-36-1)

1-(Trimethylsiloxy)cyclohexene, identified by the Chemical Abstracts Service Number (CAS No.) 6651-36-1, is a significant compound in the field of organic synthesis and pharmaceutical chemistry. This molecule, featuring a cyclohexene backbone modified with a trimethylsiloxy group, has garnered attention due to its versatile applications in synthetic transformations and potential utility in drug development.

The trimethylsiloxy (TMSO) moiety is a crucial functional group in modern synthetic chemistry, known for its stability and reactivity under various conditions. The presence of this group in 1-(Trimethylsiloxy)cyclohexene enhances its utility as an intermediate in the synthesis of more complex molecules. The cyclohexene ring, a common structural motif in natural products and pharmaceuticals, provides a stable framework for further functionalization.

In recent years, 1-(Trimethylsiloxy)cyclohexene has been explored in the development of novel synthetic methodologies. One notable application is its use as a precursor in the synthesis of enantiomerically pure compounds, which are highly sought after in pharmaceutical research. The siloxy group facilitates asymmetric transformations, enabling the construction of chiral centers with high enantioselectivity. This has opened new avenues for the preparation of biologically active molecules with improved pharmacological properties.

The compound's reactivity also makes it valuable in cross-coupling reactions, such as Suzuki-Miyaura and Heck couplings, which are fundamental to constructing complex organic frameworks. The silicon-based functionality allows for easy manipulation under mild conditions, often avoiding harsh reagents or high temperatures that might degrade sensitive intermediates.

Recent studies have highlighted the role of 1-(Trimethylsiloxy)cyclohexene in polymer chemistry. Its incorporation into polymer backbones can enhance material properties such as thermal stability and flexibility. Researchers have demonstrated its use in the synthesis of siloxane-based polymers, which exhibit unique mechanical and chemical resistance characteristics. These materials are particularly relevant in industries requiring durable and high-performance polymers.

Another emerging area of interest is the application of 1-(Trimethylsiloxy)cyclohexene in medicinal chemistry. The compound's structural features make it a promising candidate for further derivatization into bioactive molecules. For instance, modifications at the cyclohexene ring or the siloxy group can lead to novel pharmacophores with potential therapeutic effects. Current research is exploring its role in developing treatments for neurological disorders, where precise molecular architecture is critical for efficacy.

The synthesis of 1-(Trimethylsiloxy)cyclohexene itself is an intriguing aspect of organic chemistry. Traditional methods involve the reaction of cyclohexene with trimethylchlorosilane in the presence of a base catalyst. However, recent advances have introduced more efficient and sustainable synthetic routes. For example, photochemical activation has been employed to achieve selective functionalization, reducing byproduct formation and improving overall yields.

In conclusion, 1-(Trimethylsiloxy)cyclohexene (CAS No. 6651-36-1) represents a versatile building block with broad applications across multiple disciplines. Its unique structural features and reactivity make it indispensable in synthetic chemistry, pharmaceutical research, and materials science. As research continues to uncover new methodologies and applications, this compound is poised to play an even greater role in advancing scientific and industrial innovation.

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