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2,5-Dimethoxytetrahydrofuran, cis + trans, 98%
2,5-Dimethoxytetrahydrofuran, cis + trans, 98%
2,5-Dimethoxytetrahydrofuran, cis + trans, 98%
Thermo Scientific Chemicals

2,5-Dimethoxytetrahydrofuran, cis + trans, 98%

CAS: 696-59-3 | C6H12O3 | 132.159 g/mol
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Catalog number A11687.36
also known as A11687-36
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500 g
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Chemical Identifiers
CAS696-59-3
IUPAC Name2,5-dimethoxyoxolane
Molecular FormulaC6H12O3
InChI KeyGFISDBXSWQMOND-UHFFFAOYNA-N
SMILESCOC1CCC(OC)O1
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SpecificationsSpecification SheetSpecification Sheet
Assay (GC)>97.5% (sum of isomers)
Refractive Index1.4160-1.4200 @ 20?C
Appearance (Color)Clear colorless to pale yellow
Identification (FTIR)Conforms
FormLiquid
2,5-Dimethoxytetrahydrofuran is a tetrahydrofuran derivative that finds application in proteomics research and in organic synthesis. It is also used as an intermediate for atropine sulfate, which is an anticholinergic drug. Further, it acts as a precursor of butanediol. In addition to this, it is used as a photographic hardener and as disinfectant in formulations.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
2,5-Dimethoxytetrahydrofuran is a tetrahydrofuran derivative that finds application in proteomics research and in organic synthesis. It is also used as an intermediate for atropine sulfate, which is an anticholinergic drug. Further, it acts as a precursor of butanediol. In addition to this, it is used as a photographic hardener and as disinfectant in formulations.

Solubility
Miscible with methanol, diethyl ether and tetrahydrofuran. Immiscible with water.

Notes
Incompatible with strong oxidizing agents and strong acids.
RUO – Research Use Only

General References:

  1. Cyclic acetal and in situ source of succindialdehyde.
  2. 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):
  3. 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).
  4. Singh, D. K.; Nath, M. Ambient temperature synthesis of beta,beta'-fused nickel(II) pyrrolo[1,2-a]pyrazinoporphyrins via a DBSA-catalyzed Pictet-Spengler approach. Org. Biomol. Chem. 2015, 13 (6), 1836-1845.
  5. Boyd, S.; Davies, R. D. M.; Degorce, S. L.; Groombridge, S.; Scott, J. S.; Stokes, S. Synthesis of novel, functionalised tricycles utilising the interrupted Pummerer reaction. Tetrahedron Lett. 2016, 57 (1), 152-154.