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| CAS No.: | 96-47-9 |
|---|---|
| Name: | 2-Methyltetrahydrofuran |
| Article Data: | 249 |
| Molecular Structure: | |
|
|
|
| Formula: | C5H10O |
| Molecular Weight: | 86.1338 |
| Synonyms: | Furan, 2-methyl-tetrahydro-;(2R)-2-methyloxolane;2-Methyloxolane;Tetrahydrosylvan;(2S)-2-methyloxolane;74069-67-3;Furan, tetrahydro-2-methyl-;Tetrahydro-2-methyl-furan; |
| EINECS: | 202-507-4 |
| Density: | 0.863 g/cm3 |
| Melting Point: | -136 °C |
| Boiling Point: | 79.9 °C at 760 mmHg |
| Flash Point: | 10.4°F |
| Solubility: | water: 15 g/100 mL (25 °C) |
| Appearance: | Clear,colorless liquid |
| Hazard Symbols: |
 F, Xi
|
| Risk Codes: | 11-19-36/37 |
| Safety: | 16-23-39-33-26 |
| Transport Information: | UN 2536 3/PG 2 |
| PSA: | 9.23000 |
| LogP: | 1.18530 |
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| Conditions | Yield |
|---|---|
| With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere; | 100% |
| With palladium-aluminum at 150℃; Hydrogenation; | |
| With osmium at 80℃; Hydrogenation; |
| Conditions | Yield |
|---|---|
| With hydrogen In isopropyl alcohol under 30003 Torr; for 5h; Reagent/catalyst; Autoclave; | 99% |
| Trichlorbutylstannan for 0.24h; | 96% |
| Nafion-H at 135℃; for 5h; | 90% |
| Conditions | Yield |
|---|---|
| With hydrogen In hexane at 180℃; for 4h; Temperature; Reagent/catalyst; Solvent; Autoclave; | 98% |
| Multi-step reaction with 2 steps 1: hydrogen / 1,4-dioxane / 2 h / 190 °C / 30003 Torr / Autoclave 2: hydrogen / 1,4-dioxane / 5 h / 190 °C / 30003 Torr / Autoclave View Scheme | |
| Multi-step reaction with 2 steps 1: hydrogen / 1,4-dioxane / 2 h / 190 °C / 30003 Torr / Autoclave 2: hydrogen / 1,4-dioxane / 5 h / 190 °C / 30003 Torr / Autoclave View Scheme |
| Conditions | Yield |
|---|---|
| With palladium on silica; copper phyllosilicate; hydrogen at 180℃; Reagent/catalyst; Inert atmosphere; | 97.1% |
| Stage #1: furfural With hydrogen at 200℃; under 760.051 Torr; Flow reactor; Stage #2: With hydrogen at 120℃; under 760.051 Torr; Temperature; Flow reactor; | 96.3% |
| With hydrogen; 5% palladium over charcoal; copper chromite catalyst E 403-TU at 175℃; under 760.051 Torr; Product distribution / selectivity; In the presence of quartz glass rings (as an evaporation zone); |
| Conditions | Yield |
|---|---|
| With tris(2,4-pentanedionato)ruthenium(III); N-butyl-N'-(4-sulfobutyl)-imidazolium p-toluenesulfonate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 160℃; under 75007.5 Torr; for 18h; Inert atmosphere; Autoclave; Ionic liquid; | 95% |
| Multi-step reaction with 2 steps 1: sodium; alcohol 2: hydrochloric acid; alcohol / 150 °C / im Druckrohr View Scheme | |
| Multi-step reaction with 2 steps 1: sodium; xylene 2: HI / auf dem Wasserbad und folgenden Reduzieren mit Zinkstaub und Eisessig View Scheme |
| Conditions | Yield |
|---|---|
| With bromopentacarbonylmanganese(I); phenylsilane In toluene at 100℃; for 24h; Catalytic behavior; Time; Temperature; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 95% |
| With Cu/SiO2 at 220℃; under 22502.3 Torr; Temperature; | 93% |
| With ammonium hexafluorophosphate; Λ(+)-tris(pentane-2,5-dionato)ruthenium; N-butyl-N'-(4-sulfobutyl)-imidazolium p-toluenesulfonate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 160℃; under 75007.5 Torr; for 18h; Inert atmosphere; | 92% |
| Conditions | Yield |
|---|---|
| With N-iodo-succinimide In chlorobenzene for 2h; Irradiation; | A 94% B 1% C n/a |
| With N-iodo-succinimide In chlorobenzene for 2h; Product distribution; Irradiation; var. irradiat. times, temps. and light cond.; | A 94% B 1% C n/a |
| Conditions | Yield |
|---|---|
| decompn. of the crude compound at 120°C (0.5 h); | A 93% B n/a |
| decompn. of the crude compound at 120°C (0.5 h); | A 93% B n/a |
| Conditions | Yield |
|---|---|
| With Nd magnetically supported catalyst In dichloromethane at 83℃; for 24h; Schlenk technique; Inert atmosphere; | 91% |
| With aluminium(III) triflate In nitromethane at 101℃; for 1h; | 87% |
| With ytterbium(III) triflate at 120℃; Inert atmosphere; Ionic liquid; | 78% |
| Conditions | Yield |
|---|---|
| With hydrogen In para-xylene at 180℃; under 30003 Torr; for 48h; Glovebox; Sealed tube; chemoselective reaction; | 90% |
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Consensus Reports
Reported in EPA TSCA Inventory.
Specification
1. Introduction of 2-Methyltetrahydrofuran
2-Methyltetrahydrofuran, can also be called Tetrahydro-2-methylfuran; Furan, tetrahydro-2-methyl-; 2-Methyl-4,5-Dihydrofuran; 2-Methyloxolane; alpha-Methyltetrahydrofuran. The IUPAC Name of it is 2-Methyloxolane. It is stable, but highly flammable. Incompatible with oxidizing agents, strong acids, strong bases. May form explosive peroxides in storage, so often supplied with an inhibitor added. Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.
2. Properties of 2-Methyltetrahydrofuran
Density: 0.86 g/cm3
Melting Point: -136 ºC
Boiling Point: 78-80 ºC
Refractive Index: 1.4046-1.4066
Flash Point: -11 ºC
Water Solubility: 15 g/100 mL (25 C)
Storage Temp.: Flammables area
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 9.23 Å2
Index of Refraction: 1.41
Molar Refractivity: 24.76 cm3
Molar Volume: 99.7 cm3
Surface Tension: 25.4 dyne/cm
Enthalpy of Vaporization: 30.74 kJ/mol
Vapour Pressure: 96.8 mmHg at 25°C
Appearance: Clear,colorless liquid
Classification Code: Skin/Eye Irritant
3. Structure Descriptors of 2-Methyltetrahydrofuran
InChI: InChI=1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
InChIKey: JWUJQDFVADABEY-UHFFFAOYAM
Std. InChI: InChI=1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3
Std. InChIKey: JWUJQDFVADABEY-UHFFFAOYSA-N
4. Toxicity of 2-Methyltetrahydrofuran
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| rabbit | LD50 | skin | 4500mg/kg (4500mg/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 395, 1969. | |
| rat | LC50 | inhalation | 6000ppm/4H (6000ppm) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 395, 1969. |
5. Safety Information of 2-Methyltetrahydrofuran
Hazard Codes:
F,
XiRisk Statements:11-19-36/37
R11:Highly flammable.
R19:May form explosive peroxides.
R36/37:Irritating to eyes and respiratory system.
Safety Statements:16-23-39-33-26
S16:Keep away from sources of ignition.
S23:Do not breathe vapour.
S39:Wear eye / face protection.
S33:Take precautionary measures against static discharges.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR:UN 2536 3/PG 2
WGK Germany:2
RTECS:LU2800000
HazardClass:3
PackingGroup:II
HS Code:29321900
6. Preparation of 2-Methyltetrahydrofuran
2-Methyltetrahydrofuran can also be produced starting from levulinic acid. Cyclization and reduction gives γ-valerolactone
This lactone can be hydrogenated to 1,4-pentanediol, which can then be dehydrated to give 2-methyltetrahydrofuran
7. Use of 2-Methyltetrahydrofuran
2-Methyltetrahydrofuran is mainly used as solvents for resin, rubber, ethyl cellulose.And it also can be used as for the synthesis of anti-disease drugs such as Primaquine Phosphate in the pharmaceutical industry.