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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.
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).
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.
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.
Hazard Statements: H226-H302-H330-H315-H319-H335
Flammable liquid and vapour. Harmful if swallowed. Fatal if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.