2,5-dimethoxyoxolane

• ChemBase ID: 123334
• Molecular Formular: C6H12O3
• Molecular Mass: 132.15768
• Monoisotopic Mass: 132.07864424
• SMILES: O1C(CCC1OC)OC
• Canonical SMILES: COC1CCC(O1)OC
• InChI: InChI=1S/C6H12O3/c1-7-5-3-4-6(8-2)9-5/h5-6H,3-4H2,1-2H3
• InChIKey: GFISDBXSWQMOND-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dimethoxyoxolane
• IUPAC Traditional name: 2,5-dimethoxyoxolane
• Synonyms: Tetrahydro-2,5-dimethoxyfuran; 2,5-Dimethoxytetrahydrofuran, mixture of cis and trans; 2,5-dimethoxytetrahydrofuran; 2,5-Dimethoxytetrahydrofuran, cis + trans; 2,5-Dimethoxytetrahydrofuran; 四氢-2,5-二甲氧基呋喃; 2,5-二甲氧基四氢呋喃，顺式和反式混合物; 2,5-二甲氧基四氢呋喃, 顺 + 反; 2,5-二甲氧基四氢呋喃

Database IDs

• CAS Number: 696-59-3
• EC Number: 211-797-1
• MDL Number: MFCD00005359
• Beilstein Number: 104261
• PubChem SID: 24893414; 24864212; 162217687
• PubChem CID: 79098

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.6307491
• LogD (pH = 7.4): 0.6307491
• Log P: 0.6307491
• Molar Refractivity: 32.3365 cm^3
• Polarizability: 13.178978 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -45°C
• Boiling Point: 143-146 °C(lit.); 145-147 °C(lit.); 145-147°C
• Flash Point: 100.4 °F; 35°C(95°F); 38 °C
• Density: 1.02 g/mL at 25 °C(lit.); 1.020; 1.023 g/mL at 20 °C(lit.)
• Refractive Index: 1.4180; n20/D 1.418; n20/D 1.418(lit.)

Safety Information

• Storage Warning: Air & Light Sensitive
• European Hazard Symbols: X; Irritant (Xi)
• UN Number: 1993; UN3271
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-20-36/37/38; 10-36/37/38
• Safety Statements: 26-36; 7-26-33-37-43
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335; H330-H302-H315-H319-H335-H226
• GHS Precautionary statements: P210-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P261-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

Product Information

• Purity: ≥97.0% (GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C6H12O3

DETAILS

Sigma Aldrich - D137103

Packaging
100, 500 g in glass bottle

REFERENCES

• Cyclic acetal and in situ source of succindialdehyde.
• Reacts with primary amines in boiling acetic acid to give N-substituted pyrroles: Acta Chem. Scand., 6, 667, 867 (1952); J. Heterocycl. Chem., 27, 1805 (1990); Org. Synth. Coll., 5, 716 (1973). Conversion to 1,4-dichloro-1,4-dimethoxybutane with TMS chloride allows cyclization with Amberlyst. A-21 resin, avoiding acidic conditions: J. Org. Chem., 48, 3059 (1983). Chiral 1-substituted pyrrole derivatives have been prepared using amino acids: Tetrahedron: Asymmetry, 7, 1069 (1996):
  
• N-substituted pyrroles have also been formed with sulfonamides and primary amides. P₂O₅ has been reported to give superior results in this type of reaction: Synth. Commun., 25, 1857 (1995).