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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-H319-H331
Flammable liquid and vapour. Causes serious eye irritation. Toxic if inhaled.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P311-P337+P313-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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. Call a POISON CENTER or doctor/physician. If eye irritation persists: Get medical advice/attention. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant