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D106208

Sigma-Aldrich

3,4-Dihydro-2H-pyran

97%

Synonym(s):

2,3,4-Trihydropyran, 2H-3,4-Dihydropyran, Dihydro-2H-pyran, Dihydropyran

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About This Item

Empirical Formula (Hill Notation):
C5H8O
CAS Number:
110-87-2
Molecular Weight:
84.12
Beilstein:
103493
EC Number:
203-810-4
MDL number:
MFCD00006558
UNSPSC Code:
12352005
PubChem Substance ID:
24893341
NACRES:
NA.22

vapor density

2.9 (vs air)

Quality Level

200

Assay

97%

form

liquid

refractive index

n20/D 1.440 (lit.)

bp

86 °C (lit.)

mp

−70 °C (lit.)

density

0.922 g/mL at 25 °C (lit.)

SMILES string

C1COC=CC1

InChI

1S/C5H8O/c1-2-4-6-5-3-1/h2,4H,1,3,5H2

InChI key

BUDQDWGNQVEFAC-UHFFFAOYSA-N

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Application

3,4-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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H317,H319,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - Skin Sens. 1B

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

5.0 °F - closed cup

Flash Point(C)

-15 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Highly selective tetrahydropyranylation/dehydropyranylation of alcohols and phenols using porous phenolsulfonic acid-formaldehyde resin catalyst under solvent-free condition
Rajkumari K, et al.
Reactive and Functional Polymers, 149, 104519-104519 (2020)
Greene, T.W. Wuts, P.G.M.
Protective Groups in Organic Synthesis, 31-31 (1991)
Christiaan Jardínez et al.
Journal of molecular modeling, 22(12), 296-296 (2016-11-28)
The relationship between the chemical structure and biological activity (log IC50) of 40 derivatives of 1,4-dihydropyridines (DHPs) was studied using density functional theory (DFT) and multiple linear regression analysis methods. With the aim of improving the quantitative structure-activity relationship (QSAR)
Debendra K Mohapatra et al.
Organic letters, 13(4), 744-747 (2011-01-11)
Highly stereoselective total syntheses of polyrhacitide A and epi-cryptocaryolone have been achieved in 11 steps with high overall yield of 24% and 28%, respectively, following a recently developed strategy for the construction of trans-2,6-disubstituted-3,4-dihydropyrans. In this report, the versatility of
Pieter Levecque et al.
Organic & biomolecular chemistry, 5(11), 1800-1806 (2007-05-24)
Venturello's peroxophosphotungstate compound and Ti(O(i)Pr)(4) were successfully used as catalysts for the epoxidation-alcoholysis of various dihydropyrans and dihydrofuran using H(2)O(2) as the oxidant. Different alcohols can be used as solvents and nucleophiles, resulting in hydroxy ether products with varying alkoxy
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