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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

5.0 °F - closed cup

flash_point_c

-15 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1553
STBK7382
STBK7122
STBK3111
STBK2831

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FeCl3-NaI mediated reactions of aryl azides with 3, 4-dihydro-2H-pyran: a convenient synthesis of pyranoquinolines
Kamal A, et al.
Tetrahedron Letters, 45, 3507-3509 (2004)
O Kenrik Duru et al.
Journal of general internal medicine, 30(11), 1645-1650 (2015-05-07)
Reducing patient cost-sharing and engaging patients in disease management activities have been shown to increase uptake of evidence-based care. To evaluate the effect of employer purchase of a disease-specific plan with reduced cost-sharing and disease management (the Diabetes Health Plan/DHP)
Synthesis and Biological Evaluation of Novel Epothilone B Side Chain Analogues
Nicolaou K, et al
ChemMedChem, 10, 1974-1979 (2015)
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)
Domino reaction of anilines with 3, 4-dihydro-2H-pyran catalyzed by cation-exchange resin in water: an efficient synthesis of 1, 2, 3, 4-tetrahydroquinoline derivatives
Chen L, et al.
Green Chemistry, 5, 627-629 (2003)
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