1-ethenyl-1-(2-methoxyethoxy)cyclopropane

• ChemBase ID: 141272
• Molecular Formular: C8H14O2
• Molecular Mass: 142.19556
• Monoisotopic Mass: 142.09937969
• SMILES: COCCOC1(CC1)C=C
• Canonical SMILES: COCCOC1(C=C)CC1
• InChI: InChI=1S/C8H14O2/c1-3-8(4-5-8)10-7-6-9-2/h3H,1,4-7H2,2H3
• InChIKey: YIUPAIQJWAOJKD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-ethenyl-1-(2-methoxyethoxy)cyclopropane
• IUPAC Traditional name: 1-ethenyl-1-(2-methoxyethoxy)cyclopropane
• Synonyms: 1-Ethenyl-1-(2-methoxyethoxy)cyclopropane; 1-(2-Methoxyethoxy)-1-vinylcyclopropane; 1-乙烯基-1-(2-甲氧基乙氧基)环丙烷; 1-(2-甲氧基乙氧基)-1-乙烯基环丙烷

Database IDs

• CAS Number: 278603-80-8
• MDL Number: MFCD08276975
• PubChem SID: 162235507
• PubChem CID: 11309570

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.198157
• LogD (pH = 7.4): 1.198157
• Log P: 1.198157
• Molar Refractivity: 40.3195 cm^3
• Polarizability: 15.877909 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 114.8 °F; 46 °C
• Density: 0.922 g/mL at 25 °C
• Refractive Index: n20/D 1.441

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-22-36
• Safety Statements: 26
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• 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

• Empirical Formula (Hill Notation): C8H14O2

DETAILS

Sigma Aldrich - 666246

Application
A useful scaffold for the preparation of 7-membered and bicyclic ring systems.6,7
Capable of participating in a variety of rhodium-catalyzed cycloaddition reactions.6,7,2
Reactant for:
• Rhodium-catalyzed [5+2] cycloaddition with alkynes1 and allenes2
• Cycloaddition/Nazarov cyclization sequence reactions3
• Preparation of cyclohexenones by cocyclization with carbon monoxide catalyzed by octacarbonyldicobalt4
• Preparation of cyclopentenes by nickel-catalyzed isomerization5
Packaging
1 g in ampule