cyclohex-2-en-1-one

• ChemBase ID: 78387
• Molecular Formular: C6H8O
• Molecular Mass: 96.12712
• Monoisotopic Mass: 96.05751488
• SMILES: O=C1CCCC=C1
• Canonical SMILES: O=C1CCCC=C1
• InChI: InChI=1S/C6H8O/c7-6-4-2-1-3-5-6/h2,4H,1,3,5H2
• InChIKey: FWFSEYBSWVRWGL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohex-2-en-1-one
• IUPAC Traditional name: cyclohexenone
• Synonyms: 2-Cyclohexen-1-one; Cyclohexenone; cyclohex-2-enone; 2-CYCLOHEXENONE-1; 1-Oxocyclohex-2-ene; Cyclohex-2-en-1-one 97+%; 2-环己烯-1-酮

Database IDs

• CAS Number: 930-68-7
• EC Number: 213-223-5
• MDL Number: MFCD00001577
• Beilstein Number: 1280477
• PubChem SID: 24857595; 162043156; 24889674; 24892309
• PubChem CID: 13594
• CHEBI ID: 15977
• Chemspider ID: 13005
• KEGG ID: C02395
• Wikipedia Title: Cyclohexenone

CALCULATED PROPERTIES

• Acid pKa: 18.76227
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.4860177
• LogD (pH = 7.4): 1.4860177
• Log P: 1.4860177
• Molar Refractivity: 29.3407 cm^3
• Polarizability: 10.882095 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Clear colorless liquid
• Melting Point: -53 °C(lit.); -53°C; -53 °C; -53°C
• Boiling Point: 167-169°C; 167-169°C; 171-173 °C(lit.); 171–173 °C
• Flash Point: 132.8 °F; 56 °C; 56°C; 56°C(132°F)
• Density: 0.993; 0.993 g/mL; 0.993 g/mL at 25 °C(lit.)
• Refractive Index: 1.4880; n20/D 1.488(lit.); n20/D 1.489
• Vapor Pressure: 760 mmHg ( 168 °C)

Safety Information

• Storage Warning: Flammable/Toxic/Light Sensitive
• RTECS: GW7000000
• European Hazard Symbols: Toxic (T)
• UN Number: 2929; UN2929
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 22-23/24; 22-23/24-36; R:22-27
• Safety Statements: 23-36/37/39-45; 9-20-23-26-27-36/37/39-45; S:28-29-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  3

  1

  0
• GHS Hazard statements: H226-H301 + H331-H310; H301-H310-H330-H319-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P261-P280-P301 + P310-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2929 6.1/PG 2

Product Information

• Purity: ≥95%; ≥95.0% (GC); ≥98.0% (GC); 97%
• Grade: produced by BASF; purum
• Impurities: ≤0.5% water
• Linear Formula: C6H8(=O)

DETAILS

MP Biomedicals - 05213885

MP Biomedicals Rare Chemical collection

Sigma Aldrich - C102814

Packaging
10, 25, 100 mL in glass bottle
Application
Versatile electrophile employed in a range of addition reactions including conjugate addition of organocopper nucleophiles,1 Michael reaction with enol silanes,2 and phosphoniosilylations.3

Sigma Aldrich - 29255

Caution
may discolor to brown on storage

REFERENCES

• Facile, selective 1,2-reduction occurs with Sodium borohydride, 35788, in the presence of CaCl₂, to give 92% yield of 2-cyclohexen-1-ol: Chem. Lett., 1847 (1991).