cyclopropanecarbaldehyde

• ChemBase ID: 150904
• Molecular Formular: C4H6O
• Molecular Mass: 70.08984
• Monoisotopic Mass: 70.04186481
• SMILES: C1CC1C=O
• Canonical SMILES: O=CC1CC1
• InChI: InChI=1S/C4H6O/c5-3-4-1-2-4/h3-4H,1-2H2
• InChIKey: JMYVMOUINOAAPA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclopropanecarbaldehyde
• IUPAC Traditional name: cyclopropanecarbaldehyde
• Synonyms: Cyclopropanecarboxaldehyde; cyclopropanecarbaldehyde; 环丙甲醛

Database IDs

• CAS Number: 1489-69-6
• EC Number: 000-000-0
• MDL Number: MFCD00012261
• Beilstein Number: 906781
• PubChem SID: 162245064; 24856460
• PubChem CID: 123114

CALCULATED PROPERTIES

• Acid pKa: 18.51209
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.39783424
• LogD (pH = 7.4): 0.39783424
• Log P: 0.39783424
• Molar Refractivity: 19.1175 cm^3
• Polarizability: 7.445063 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 198 - 200°C
• Boiling Point: 98-101 °C(lit.); 98-101°C
• Flash Point: 44.6 °F; 7 °C; 7°C(44°F)
• Density: 0.938; 0.938 g/mL at 25 °C(lit.)
• Refractive Index: 1.4298; n20/D 1.4298(lit.)
• Hydrophobicity(logP): 0.13

Safety Information

• Storage Warning: Air Sensitive
• RTECS: GZ1005000
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-34
• Safety Statements: 16-26-36/37/39-45; 20-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 98%
• Linear Formula: C3H5CHO

DETAILS

Sigma Aldrich - 272213

Application
Used to prepare a cyclopropylidene tetralone which underwent an enantioselective palladium-catalyzed [3+2] TMM cycloaddition providing a chiral spiro-fused cyclopentene.1
Versatile reagent for the introduction of a cyclopropyl moiety into a substrate
Packaging
1, 5 g in glass bottle

REFERENCES

• Reacts with Grignard or organolithium reagents to give the expected secondary alcohols. These are susceptible to ring opening in the presence of HBr, providing stereoselective access to homoallylic bromides: Synth. Commun., 25, 3351 (1995):