(cyclohex-1-en-1-yloxy)trimethylsilane

• ChemBase ID: 54689
• Molecular Formular: C9H18OSi
• Molecular Mass: 170.32412
• Monoisotopic Mass: 170.11269173
• SMILES: C1(=CCCCC1)O[Si](C)(C)C
• Canonical SMILES: C[Si](OC1=CCCCC1)(C)C
• InChI: InChI=1S/C9H18OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h7H,4-6,8H2,1-3H3
• InChIKey: SBEMOANGDSSPJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (cyclohex-1-en-1-yloxy)trimethylsilane
• IUPAC Traditional name: (cyclohex-1-en-1-yloxy)trimethylsilane
• Synonyms: 1-Cyclohexenyloxytrimethylsilane; Cyclohexanone enol trimethylsilyl ether; 1-(Trimethylsiloxy)cyclohexene; 1-(Trimethylsilyloxy)cyclohexene; 1-(Trimethylsiloxy)cyclohexene; 1-环己烯氧基三甲基硅烷; 1-(三甲基硅氧基)环己烯; 1-(三甲基硅氧烷)环己烯

Database IDs

• CAS Number: 6651-36-1
• EC Number: 229-675-1
• MDL Number: MFCD00001541
• Beilstein Number: 1859394
• PubChem SID: 24848686; 24889700; 162059452
• PubChem CID: 81161

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.4375
• LogD (pH = 7.4): 2.4375
• Log P: 2.4375
• Molar Refractivity: 46.8948 cm^3
• Polarizability: 19.962593 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 165°C; 64-65 °C/15 mmHg(lit.); 64-65°C/15mm
• Flash Point: 105.8 °F; 41 °C; 42°C; 42°C(107°F)
• Density: 0.875; 0.875 g/mL at 25 °C(lit.); 0.883
• Refractive Index: 1.447; 1.4470; n20/D 1.447; n20/D 1.447(lit.)

Safety Information

• Storage Warning: Flammable/Keep Cold/Moisture Sensitive; IRRITANT; Moisture Sensitive
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10
• TSCA Listed: false; 是
• GHS Pictograms: GHS02
• GHS Signal Word: Warning
• GHS Hazard statements: H226; H226-H303
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 98%; 99%
• Grade: purum
• Linear Formula: C6H9OSi(CH3)3

DETAILS

Sigma Aldrich - 144819

Application
Intermediate to many complex compounds including natural products.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 92735

Other Notes
Review1

REFERENCES

• Silyl enol ethers undergo crossed aldol condensations with aldehydes and ketones: J. Am. Chem. Soc., 96, 7503 (1974); for tabulated results, see: Org. Synth. Coll., 8, 323 (1993):
  
• For reviews of the chemistry of silyl enol ethers, see: Synthesis, 91 (1977); 85 (1983).
• Condensation with aldehydes is also promoted by F^-, particularly TBAF: J. Org. Chem., 48, 932 (1983).
• The Lewis acid-catalyzed condensation with nitroalkenes leads to 1,4-diketones: J. Am. Chem. Soc., 98, 4679 (1976); Org. Synth. Coll, 7, 414 (1990).