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3,4-Dihydro-2H-pyran

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3,4-Dihydro-2H-pyran Basic information
Product Name:3,4-Dihydro-2H-pyran
Synonyms:3,4-dihydro-2h-pyra;3,4-Dihydro-2-pyran;delta(Sup2)-Dihydropyran;delta2-Dihydropyran;Pyran, dihydro-;pyran,dihydro-;δ2-dihydropyran;DIHYDROPYRAN
CAS:110-87-2
MF:C5H8O
MW:84.12
EINECS:203-810-4
Product Categories:Halogenated Heterocycles ,Isoquinolines ,Quinolines ,Quinazolines ,Quinaldines;Protection and Derivatization;Others;Protecting and Derivatizing Reagents;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Oxygen cyclic compounds
Mol File:110-87-2.mol
3,4-Dihydro-2H-pyran Structure
3,4-Dihydro-2H-pyran Chemical Properties
Melting point -70 °C (lit.)
Boiling point 86 °C (lit.)
density 0.922 g/mL at 25 °C (lit.)
vapor density 2.9 (vs air)
vapor pressure 77.8 hPa (20 °C)
refractive index n20/D 1.440(lit.)
Fp 4 °F
storage temp. Store below +30°C.
solubility 7.7g/l
form Liquid
color Clear colorless to yellow
PH7 (5g/l, H2O, 20℃)
explosive limit1.1-13.8%(V)
Water Solubility 20 g/L (20 ºC)
BRN 103493
Stability:Volatile
InChI1S/C5H8O/c1-2-4-6-5-3-1/h2,4H,1,3,5H2
InChIKeyBUDQDWGNQVEFAC-UHFFFAOYSA-N
SMILESC1COC=CC1
LogP0.690
CAS DataBase Reference110-87-2(CAS DataBase Reference)
NIST Chemistry Reference2H-Pyran, 3,4-dihydro-(110-87-2)
EPA Substance Registry System2H-Pyran, 3,4-dihydro- (110-87-2)
Safety Information
Hazard Codes F,Xi
Risk Statements 11-36/37/38-36/38-19
Safety Statements 16-26-36-37/39-33-7/9
RIDADR UN 2376 3/PG 2
WGK Germany 3
RTECS UP7700000
Autoignition Temperature240 °C
Hazard Note Highly Flammable/Irritant
TSCA TSCA listed
HazardClass 3
PackingGroup II
HS Code 29329995
Storage Class3 - Flammable liquids
Hazard ClassificationsAquatic Chronic 3
Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
Skin Sens. 1B
ToxicityLD50 orally in Rabbit: > 4000 mg/kg
MSDS Information
ProviderLanguage
3,4-Dihydro-2H-pyran English
ACROS English
SigmaAldrich English
ALFA English
3,4-Dihydro-2H-pyran Usage And Synthesis
Chemical Propertiescolorless to light yellow liqui
UsesWidely used hydroxyl-protecting reagent3,4-Dihydro-2H-pyran is used as a hydroxyl-protecting reagent in organic synthesis. It acts as an intermediate in synthetic chemistry. It is used to protect various reactive functional groups. It is involved in the polymerization reaction either alone or with unsaturated compound and finds application in polymer industries. Further, it is employed in the preparation of bicyclic compounds of epoxide-fused, halo compounds and allenic alcohols.
Application3,4-Dihydro-2H-pyran can be used as a reactant to synthesize:
  • Tetrahydropyranylated product from alcohols in the presence of phenolsulfonic acid-formaldehyde resin catalyst.
  • Tetrahydropyran derivatives by reacting pyrazoles in the presence of trifluoroacetic acid.
  • 1,2,3,4-Tetrahydroquinoline derivatives by cation-exchange resin catalyzed Domino reaction with aromatic amines.
  • Tetrahydroquinolines from aryl azides in the presence of FeCl3-NaI.
Flammability and ExplosibilityFlammable
Safety ProfileA flammable and very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidzing materials. Keep away from heat and open flame. To fight fire, use alcohol foam, CO2, or dry chemical. When heated to decomposition it emits acrid smoke and irritating
Purification MethodsPartially dry dihydropyran with Na2CO3, then fractionally distil it. The fraction b 84-85o is refluxed with Na until hydrogen no longer evolves when fresh Na is added. It is then dried, and distilled again through a 60 x 1.2cm column packed with glass rings [Brandon et al. J Am Chem Soc 72 2120 1950, UV: Elington et al. J Chem Soc 2873 1952, NMR: Bushweller & O'Neil Tetrahedron Lett 4713 1969]. It has been characterised as the 3,5-dinitrobenzoyloxy-tetrahydrofuran derivative, m 103o which forms pale yellow crystals from dihydropyran/Et2O [Woods & Kramer J Am Chem Soc 69 2246 1947]. [Beilstein 17/1 V 181.]
Tag:3,4-Dihydro-2H-pyran(110-87-2) Related Product Information
Sodium phosphate dibasic dodecahydrate Tetrahydro-4H-pyran-4-one Centchroman Ammonium dihydrogen phosphate Dipotassium hydrogen phosphate trihydrate Aluminum dihydrogen phosphate Boron nitride 3,4-DIHYDRO-2-METHOXY-2H-PYRAN LOGANIC ACID Oleuropein 2-ETHOXY-3,4-DIHYDROPYRAN Harpagoside VERBENALIN PICROSIDE I Picroside II Geniposide CITRININ sodium 3,4-dihydro-2H-pyran-2-carboxylate