2-methoxyprop-1-ene

• ChemBase ID: 78178
• Molecular Formular: C4H8O
• Molecular Mass: 72.10572
• Monoisotopic Mass: 72.05751488
• SMILES: O(C(=C)C)C
• Canonical SMILES: COC(=C)C
• InChI: InChI=1S/C4H8O/c1-4(2)5-3/h1H2,2-3H3
• InChIKey: YOWQWFMSQCOSBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methoxyprop-1-ene
• IUPAC Traditional name: isopropenyl methyl ether
• Synonyms: 2-Methoxyprop-1-ene; Methyl isopropenyl ether; 2-Methoxypropene; 2-Methoxypropene; Isopropenyl methyl ether; 2-Methoxyprop-1-ene; 甲基异丙烯基醚; 2-甲氧基丙烯

Database IDs

• CAS Number: 116-11-0
• EC Number: 204-125-3
• MDL Number: MFCD00014929
• Beilstein Number: 1734635
• PubChem SID: 24886415; 162042991; 24881402; 24850352
• PubChem CID: 8300
• Chemspider ID: 7999
• Wikipedia Title: 2-Methoxypropene

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.70156324
• LogD (pH = 7.4): 0.70156324
• Log P: 0.70156324
• Molar Refractivity: 22.5238 cm^3
• Polarizability: 8.548852 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colorless liquid
• Boiling Point: 34-36 °C; 34-36 °C(lit.); 35-36°C
• Flash Point: -20.2 °F; -29 °C; -29°C(-20°F)
• Auto Ignition Point: 374 °F
• Density: 0.753 g/mL; 0.753 g/mL at 25 °C(lit.); 0.758; 0.766 g/mL at 20 °C
• Refractive Index: 1.3835; n20/D 1.382; n20/D 1.382(lit.)
• Vapor Pressure: 27.96 psi ( 55 °C); 8.28 psi ( 20 °C)

Safety Information

• Storage Warning: Flammable/Harmful/Keep Cold/Light Sensitive; Light Sensitive
• RTECS: UD0800000
• European Hazard Symbols: Flammable (F); Highly flammable (F+); X; Harmful (Xn)
• UN Number: 1993; UN1993
• German water hazard class: 1; 2
• Hazard Class: 3
• Packing Group: 1; I
• Risk Statements: 11-19-22; 12-19-22
• Safety Statements: 16; 3/7-9-16-29-33-36; 3-7/9-16-29-33
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H224-H301; H224-H302
• GHS Precautionary statements: P210; P210-P241-P301+P310-P303+P361+P353-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 1
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); ≥99.5% (GC); 95%, stab. with ca 0.5% potassium carbonate; 97%
• Grade: analytical standard; produced by BASF
• Impurities: ≤0.2% water
• Contains: potassium carbonate as stabilizer
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH2=C(CH3)OCH3

DETAILS

Sigma Aldrich - 174645

Packaging
50, 250 g in glass bottle
Application
Used to protect adjacent hydroxyls in inositols as bisacetonides,1 and 1,2-diols in general.2

Sigma Aldrich - 59262

Other Notes
Reagent for the kinetic acetonation of carbohydrates1

REFERENCES

• Can be used, in the presence of an acid catalyst, for the introduction of the methoxyisopropyl protecting group for alcohols, readily removed under mild acid conditions. Unlike dihydropyran, the resulting acetals do not contain additional chiral centers (i.e. only a single diastereomer results): J. Am. Chem. Soc., 89, 3366 (1967); 94,7827 (1972); 100, 4616 (1978).
• Diols have been protected as their acetonides in the presence of dry HBr in dichloromethane: J. Am. Chem. Soc., 100, 4620 (1978), or TsOH in DMF: J. Chem. Soc., Chem. Commun., 21 (1980), used for selective protection of a 1,3- rather than a 1,2-diol in a sugar.