2-methyl tetrahydrofuran
furan, tetrahydro-2-methyl-
Identification
| Name | 2-methyl tetrahydrofuran |
| IUPAC | 2-methyloxolane |
| CAS Number | 96-47-9 |
| EINECS | 202-507-4 |
| FDA UNII | FCD0VD8ALF |
| Molecular Formula | C5 H10 O |
| Molecular Weight | 86.13390000 |
| MDL Number | MFCD00005367 |
| Nikkaji Number | J49.588C |
| Beilstein | 0102448 |
| CoE Number | 10964 |
Regulatory
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.85300 to 0.85700 @ 20.00 °C. |
| Pounds per Gallon - (est). | 7.106 to 7.139 |
| Refractive Index | 1.40300 to 1.40700 @ 20.00 °C. |
| Boiling Point | 78.00 to 80.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 96.759003 mmHg @ 25.00 °C. (est) |
| Flash Point | 12.00 °F. TCC ( -11.11 °C. ) |
| logP (o/w) | 1.008 (est) |
| Shelf Life | 6.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
| Insoluble in | water |
Organoleptic Properties
| Substantivity | 4 Hour(s) |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | skin-rabbit LD50 4500 mg/kg |
| Inhalation Toxicity | inhalation-rat LC50 6000 ppm/4H |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 2-methyl tetrahydrofuran usage levels up to | not for fragrance use. |
Penta International Corporation
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Potential Uses
Natural Occurrence
Synonyms
furan, 2-methyl-tetrahydro-
furan, tetrahydro-2-methyl-
2-
methyl oxolane
2-
methyl-4,5-dihydrofuran
2-
methyloxolane
2-
methyltetrahydrofuran
tetrahydro-2-methyl furan
tetrahydro-2-methylfuran
tetrahydrofuran, 2-methyl-
PubMed:
Direct Detection of a Triplet Vinylnitrene, 1,4-Naphthoquinone-2- ylnitrene in Solution and Cryogenic Matrices.
PubMed:
Direct transformation of xylan-type hemicelluloses to furfural via SnCl4 catalysts in aqueous and biphasic systems.
PubMed:
A "naked" Fe(III)-(Oâ²â»)-Cu(II) species allows for structural and spectroscopic tuning of low-spin heme-peroxo-Cu complexes.
PubMed:
Hydroxo radicals, C-H activation, and Pt-C bond formation from 77 K photolysis of a platinum(IV) hydroxo complex.
PubMed:
Highly efficient and enzymatic regioselective undecylenoylation of gastrodin in 2-methyltetrahydrofuran-containing systems.
PubMed:
Conformational control of oligo(p-phenyleneethynylene)s with intrinsic substituent electronic effects: origin of the twist in pentiptycene-containing systems.
PubMed:
A unified strategy for iron-catalyzed ortho-alkylation of carboxamides.
PubMed:
Efficient, solvent-free hydrogenation of α-angelica lactone catalysed by Ru/C at atmospheric pressure and room temperature.
PubMed:
Photoreduction of Pt(IV) chloro complexes: substrate chlorination by a triplet excited state.
PubMed:
Highly efficient enzymatic synthesis of an ascorbyl unstaturated fatty acid ester with ecofriendly biomass-derived 2-methyltetrahydrofuran as cosolvent.
PubMed:
Photophysics of platinum tetrayne oligomers: delocalization of triplet exciton.
PubMed:
Low-temperature combustion chemistry of novel biofuels: resonance-stabilized QOOH in the oxidation of diethyl ketone.
PubMed:
Excited state properties of chlorophyll f in organic solvents at ambient and cryogenic temperatures.
PubMed:
Excitation wavelength dependent O2 release from copper(II)-superoxide compounds: laser flash-photolysis experiments and theoretical studies.
PubMed:
Measurement of the relative mobility of geminate ions in ethereal solutions of aromatic compounds using the fluorescence response of the solutions to pulsed irradiation.
PubMed:
High-spin S = 2 ground state aminyl tetraradicals.
PubMed:
Catalytic transfer hydrogenation/hydrogenolysis for reductive upgrading of furfural and 5-(hydroxymethyl)furfural.
PubMed:
Stepwise protonation and electron-transfer reduction of a primary copper-dioxygen adduct.
PubMed:
2-Methyltetrahydrofuran and cyclopentylmethylether: two green solvents for efficient purification of membrane proteins like FhuA.
PubMed:
Plant-derived juvenile hormone III analogues and other sesquiterpenes from the stem bark of Cananga latifolia.
PubMed:
U-shaped temperature dependence of rate constant of intramolecular photoinduced charge separation in zinc-porphyrin-bridge-quinone compounds.
PubMed:
Reaction kinetics of hydrogen abstraction reactions by hydroperoxyl radical from 2-methyltetrahydrofuran and 2,5-dimethyltetrahydrofuran.
PubMed:
Critical practical aspects in the application of liquid chromatography-mass spectrometric studies for the characterization of impurities and degradation products.
PubMed:
Chemoselective CaO-mediated acylation of alcohols and amines in 2-methyltetrahydrofuran.
PubMed:
Highly efficient and regioselective acylation of pharmacologically interesting cordycepin catalyzed by lipase in the eco-friendly solvent 2-methyltetrahydrofuran.
PubMed:
Enzymatic regioselective acylation of nucleosides in biomass-derived 2-methyltetrahydrofuran: kinetic study and enzyme substrate recognition.
PubMed:
Mesolysis of radical anions of tetra-, penta-, and hexaphenylethanes.
PubMed:
Efficient synthesis of phosphatidylserine in 2-methyltetrahydrofuran.
PubMed:
2-Methyltetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry.
PubMed:
Ligand-localized triplet-state photophysics in a platinum(II) terpyridyl perylenediimideacetylide.
PubMed:
Intimate electronic coupling in cationic homodimeric iridium(III) complexes.
PubMed:
Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent.
PubMed:
Electronic excitation spectra of radical anions of cyanoethylenes and cyanobenzenes: symmetry adapted cluster-configuration interaction study.
PubMed:
M-M bond-stretching energy landscapes for M2(dimen)4(2+) (M = Rh, Ir; dimen = 1,8-diisocyanomenthane) complexes.
PubMed:
Intramolecular charge resonance in dimer radical anions of di-, tri-, tetra-, and pentaphenylalkanes.
PubMed:
Kinetics and thermochemistry of 2,5-dimethyltetrahydrofuran and related oxolanes: next next-generation biofuels.
PubMed:
Enhanced asymmetric induction for the copolymerization of CO2 and cyclohexene oxide with unsymmetric enantiopure salenCo(III) complexes: synthesis of crystalline CO2-based polycarbonate.
PubMed:
New method for C-H arylation/alkylation at α-position of cyclic aliphatic ethers by iron-oxide mediated reaction.
PubMed:
Terpenoids and hexenes from the leaves of Crataegus pinnatifida.
PubMed:
Direct hydrocyclization of biomass-derived levulinic acid to 2-methyltetrahydrofuran over nanocomposite copper/silica catalysts.
PubMed:
Strain effects in electron spin resonance spectroscopy of quintet 2,6-bis(4'-nitrenophenyl)-4-phenylpyridine.
PubMed:
Conformationally constrained macrocyclic diporphyrin-fullerene artificial photosynthetic reaction center.
PubMed:
Two glass transitions and secondary relaxations of methyltetrahydrofuran in a binary mixture.
PubMed:
Thermodynamic and molecular-scale analysis of new systems of water-soluble hydrate formers + CH4.
PubMed:
One-step catalytic transformation of carbohydrates and cellulosic biomass to 2,5-dimethyltetrahydrofuran for liquid fuels.
PubMed:
Highly luminescent tetradentate bis-cyclometalated platinum complexes: design, synthesis, structure, photophysics, and electroluminescence application.
PubMed:
Electronic spectra of two long-lived photoproducts: double-proton transfer in 7-hydroxyquinoline dimer in a 2-methyltetrahydrofuran glass matrix.
PubMed:
Electron spin resonance studies of the reorientational motion of Ni(mnt)2(-).
PubMed:
Copper(I)/O2 chemistry with imidazole containing tripodal tetradentate ligands leading to mu-1,2-peroxo-dicopper(II) species.
PubMed:
Molecular structure and magnetic parameters of septet 2,4,6-trinitrenotoluene.
PubMed:
Temperature dependence of blue phosphorescent cyclometalated Ir(III) complexes.
PubMed:
A push-pull aromatic chromophore with a touch of merocyanine.
PubMed:
Syntheses, structural characterization and photophysical properties of 4-(2-pyridyl)-1,2,3-triazole rhenium(I) complexes.
PubMed:
Triplet formation involving a polar transition state in a well-defined intramolecular perylenediimide dimeric aggregate.
PubMed:
Unexpectedly similar charge transfer rates through benzo-annulated bicyclo[2.2.2]octanes.
PubMed:
Theoretical study of pyrazolate-bridged dinuclear platinum(II) complexes: interesting potential energy curve of the lowest energy triplet excited state and phosphorescence spectra.
PubMed:
Photophysics of diplatinum polyynediyl oligomers: chain length dependence of the triplet state in sp carbon chains.
PubMed:
Copper(I) complex O(2)-reactivity with a N(3)S thioether ligand: a copper-dioxygen adduct including sulfur ligation, ligand oxygenation, and comparisons with all nitrogen ligand analogues.
PubMed:
Photophysical properties of highly luminescent copper(I) halide complexes chelated with 1,2-bis(diphenylphosphino)benzene.
PubMed:
Structures of the hexafluorocyclopropane, octafluorocyclobutane, and decafluorocyclopentane radical anions probed by experimental and computational studies of anisotropic electron spin resonance (ESR) spectra.
PubMed:
Dioxygen reactivity of a copper(I) complex with a N3S thioether chelate; peroxo-dicopper(II) formation including sulfur-ligation.
PubMed:
Dual fluorescence from an isonido ReIII rhenacarborane phosphine complex, [7,10-mu-H-7-CO-7,7-(PPh3)2-isonido-7,8,9-ReC2B7H9].
PubMed:
Emission spectroscopic investigation of triplet diarylcarbene generated in molecular sieve VPI-5.
PubMed:
Photoinduced long-lived charge separation in a tetrathiafulvalene-porphyrin-fullerene triad detected by time-resolved electron paramagnetic resonance.
PubMed:
Dual electron transfer pathways from 4,4'-dimethoxybenzophenone ketyl radical in the excited state to parent molecule in the ground state.
PubMed:
Ultrafast energy migration in platinum(II) diimine complexes bearing pyrenylacetylide chromophores.
PubMed:
Structures of tetrafluorocyclopropene, hexafluorocyclobutene, octafluorocyclopentene and related perfluoroalkene radical anions revealed by electron spin resonance spectroscopic and computational studies.
PubMed:
Conversion of intramolecular singlet electron transfer at room temperature into triplet energy transfer at 77 K: photoisomerization in norbornadiene- and carbazole-labeled poly(aryl ether) dendrimers.
PubMed:
Synthesis and characterization of ruthenacarborane complexes incorporating chelating N-donor ligands: unexpected luminescence from the complex [3-CO-3,3-kappa2-Me2N(CH2)2NMe2]-closo-3,1,2-RuC2B9H11].
PubMed:
Electronic coupling effects on photoinduced electron transfer in carotene-porphyrin-fullerene triads detected by time-resolved EPR.
PubMed:
Europium(II) and ytterbium(II) cyclic organohydroborates with agostic interactions.
PubMed:
Photochemistry of 4-(2-nitrophenyl)-1,4-dihydropyridines. Evidence for electron transfer and formation of an intermediate.
PubMed:
Triplet excitation transfer in glassy systems: spatial and spectral diffusion.
PubMed:
Platinum(II) 1,10-phenanthroline complexes of acetylides containing redox-active groups.
PubMed:
Synthesis and characterization of phenanthrylphosphine gold complex: observation of Au-induced blue-green phosphorescence at room temperature.
PubMed:
Generation and characterization of highly strained dibenzotetrakisdehydro[12]- and dibenzopentakisdehydro[14]annulenes.
PubMed:
Competition between superexchange-mediated and sequential electron transfer in a bridged donor-acceptor system.
PubMed:
Dynamics of glass-forming liquids. VIII. Dielectric signature of probe rotation and bulk dynamics in branched alkanes.
PubMed:
Triplet diphenylcarbenes protected by o-Aryl groups.
PubMed:
Solvent control of spin-dependent charge recombination mechanisms within donor-conjugated bridge-acceptor molecules.
PubMed:
Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore perylene-3,4:9,10-bis(dicarboximide) building blocks.
PubMed:
Spin delocalization by triple-bonded functionalities in propargyl and heteropropargyl radicals, assessed from the EPR-spectral D parameter of 1,3-cyclopentanediyl triplet diradicals.
PubMed:
Excited-state symmetry breaking in cofacial and linear dimers of a green perylenediimide chlorophyll analogue leading to ultrafast charge separation.
PubMed:
Spin delocalization in 1-heteroallyl monoradicals as a measure of radical stabilization by heterovinyl substituents assessed through the EPR-spectral zero-field D parameter of 1,3-cyclopentanediyl triplet diradicals.
PubMed:
Hydrogen atom abstraction reactions of charged polyaromatic sigma-radicals related to the active intermediates of the enediyne antitumor drugs.
PubMed:
The EPR-Spectral D Parameter of Photochemically Generated Cyclopentane-1,3-diyl Triplet Diradicals as a Quantitative Measure of Spin Delocalization in Vinyl-, Phenyl-, and Carbonyl-Substituted Radicals.
PubMed:
Photoswitched singlet energy transfer in a porphyrin-spiropyran dyad.
PubMed:
Synthesis and characterization of several dicopper(I) complexes and a spin-delocalized dicopper(I,II) mixed-valence complex using a 1,8-naphthyridine-based dinucleating ligand.
PubMed:
Driving force and electronic coupling effects on photoinduced electron transfer in a fullerene-based molecular triad
PubMed:
Steric influence of E- or Z-monosubstituted and terminally disubstituted vinyl groups in matrix-isolated cyclopentane-1,3-diyl triplet diradicals as probed by the zero-field EPR D parameter
PubMed:
The D parameter of vinyl-substituted 1,3-cyclopentanediyl triplet diradicals as a sensitive tool To determine electronic substituent effects in allylic radicals
PubMed:
Reactivity of Cl-P(+)-Cl toward cyclic organic ethers.
PubMed:
The D Parameter (EPR Zero-Field Splitting) of Localized 1,3-Cyclopentanediyl Triplet Diradicals as a Measure of Electronic Substituent Effects on the Spin Densities in Para-Substituted Benzyl-Type Radicals.
PubMed:
Phosphorescence of nucleic acids and DNA components at 77 K.
PubMed:
Some aspects of room-temperature phosphorescence in liquid solutions.
PubMed:
2-methyltetrahydrofuran--lithium hexafluoroarsenate: a superior electrolyte for the secondary lithium electrode.
PubMed:
EPR study of the effect of concentration on the mechanism of the photochemical reaction of acridine and quinoline with 2-methyltetrahydrofuran.
PubMed:
Delineation of the intimate details of the backbone conformation of pyridine nucleotide coenzymes in aqueous solution.