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HomeProduct name list3,4-Dihydro-2H-pyran

3,4-Dihydro-2H-pyran

Synonym(s):3,4-Dihydro-2H-pyran

  • CAS NO.:110-87-2
  • Empirical Formula: C5H8O
  • Molecular Weight: 84.12
  • MDL number: MFCD00006558
  • EINECS: 203-810-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 16:48:35
3,4-Dihydro-2H-pyran Structural

What is 3,4-Dihydro-2H-pyran?

Description

Dihydropyran (DHP) is an organic compound commonly used to install tetrahydropyranyl (THP) protecting groups on alcohols and amines.

Chemical properties

colorless to light yellow liqui

The Uses of 3,4-Dihydro-2H-pyran

Widely 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.

The Uses of 3,4-Dihydro-2H-pyran

3,4-Dihydro-2H-pyran
A mixture of the SM (4.1 g, 20 mmol), 3,4-dihydro-2H-pyran (2.0 g, 24 mmol), and p-TsOH monohydrate (100 mg, 0.52 mmol) in anhydrous DCM (70 mL) was stirred at RT for 16 h. The mixture was diluted with DCM and washed with sat aq NaHCO3, then brine. The org layer was separated, dried (Na2SO4), and concentrated in vacuo. The resulting material was purified by silica gel chromatography (0-10% EtOAc/hexane) to provide the product as a clear oil. [4.36 g, 75%]

Flammability and Explosibility

Flammable

Safety Profile

A 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 Methods

Partially 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.]

Properties of 3,4-Dihydro-2H-pyran

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.)
Flash point: 4 °F
storage temp.  Store below +30°C.
solubility  7.7g/l
form  Liquid
appearance Colorless liquid
color  Clear colorless to yellow
PH 7 (5g/l, H2O, 20℃)
explosive limit 1.1-13.8%(V)
Water Solubility  20 g/L (20 ºC)
BRN  103493
Stability: Volatile
CAS DataBase Reference 110-87-2(CAS DataBase Reference)
NIST Chemistry Reference 2H-Pyran, 3,4-dihydro-(110-87-2)
EPA Substance Registry System 2H-Pyran, 3,4-dihydro- (110-87-2)

Safety information for 3,4-Dihydro-2H-pyran

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 3,4-Dihydro-2H-pyran

InChIKey BUDQDWGNQVEFAC-UHFFFAOYSA-N

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