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A11687 2,5-Dimethoxytetrahydrofuran, cis + trans, 98%

CAS Number
696-59-3
Synonyms

Stock No. Size Price ($) Quantity Availability
A11687-22 100g 38.60
A11687-36 500g 130.00
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2,5-Dimethoxytetrahydrofuran, cis + trans, 98%

MDL
MFCD00005359
EINECS
211-797-1

Chemical Properties

Formula
C6H12O3
Formula Weight
132.16
Melting point
-45°
Boiling Point
145-147°
Flash Point
35°(95°F)
Density
1.020
Refractive Index
1.4180
Storage & Sensitivity
Air Sensitive. Light Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Miscible with methanol, diethyl ether and tetrahydrofuran. Immiscible with water.

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.

Notes

Incompatible with strong oxidizing agents and strong acids.

Literature 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).

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.

GHS Hazard and Precautionary Statements

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

Other References

Beilstein
104261
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2932.19
TSCA
Yes

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