1-methoxypropa-1,2-diene

• ChemBase ID: 141511
• Molecular Formular: C4H6O
• Molecular Mass: 70.08984
• Monoisotopic Mass: 70.04186481
• SMILES: COC=C=C
• Canonical SMILES: COC=C=C
• InChI: InChI=1S/C4H6O/c1-3-4-5-2/h4H,1H2,2H3
• InChIKey: RRWJXAJEGRDMQH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methoxypropa-1,2-diene
• IUPAC Traditional name: 1-methoxypropa-1,2-diene
• Synonyms: Methyl propadienyl ether; NSC 363923; 1-Methoxy-1,2-propadiene; Methoxyallene; 1-甲氧基-1,2-丙二烯; 甲氧基丙二烯

Database IDs

• CAS Number: 13169-00-1
• MDL Number: MFCD00153022
• PubChem SID: 162235745
• PubChem CID: 139403

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.86614585
• LogD (pH = 7.4): 0.86614585
• Log P: 0.86614585
• Molar Refractivity: 20.9864 cm^3
• Polarizability: 7.9985356 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: -18.4 °F; -28 °C
• Density: 0.832 g/mL at 25 °C
• Refractive Index: n20/D 1.429

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Grade: technical grade
• Empirical Formula (Hill Notation): C4H6O

DETAILS

Sigma Aldrich - 694126

Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Multicomponent reactions with nitriles and carboxylic acids followed by cyclocondensation for synthesis of enantiopure pyridines1
• Intermolecular hydroamination2
• One-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and dihydropyridines3
• Intermolecular [4+2] cycloaddition with dienes4
• Allenyl cyclization and subsequent transformation into dicarbonyl, cyclopentenones, and butenolide compounds5
• Insertion reactions of C-C pi-bonds into alkylidenesilacyclopropanes6