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293105

Sigma-Aldrich

Tetrahydropyran

anhydrous, 99%

Synonym(s):

Pentamethylene oxide

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About This Item

Empirical Formula (Hill Notation):
C5H10O
CAS Number:
Molecular Weight:
86.13
Beilstein:
102436
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.21

grade

anhydrous

Quality Level

vapor density

3 (vs air)

Assay

99%

form

liquid

impurities

<0.003% water
<0.005% water (100 mL pkg)

evapn. residue

<0.0003%

refractive index

n20/D 1.42 (lit.)

bp

88 °C (lit.)

mp

−45 °C (lit.)

density

0.881 g/mL at 25 °C (lit.)

SMILES string

C1CCOCC1

InChI

1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2

InChI key

DHXVGJBLRPWPCS-UHFFFAOYSA-N

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General description

Tetrahydropyran (THP) is a saturated cyclic ether. It is commonly used as a solvent in organic synthesis because of its strong hydrophobicity and low vaporization temperature, which enable easy recovery and reuse of the solvent. This makes the entire synthetic process more environmentally friendly.

Application

Tetrahydropyran can be used as a solvent in various classical organic reactions such as radical reactions, palladium-catalyzed coupling, and Grignard reactions.

Pictograms

Flame

Signal Word

Danger

Hazard Statements

Hazard Classifications

Flam. Liq. 2

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

3.2 °F - closed cup

Flash Point(C)

-16 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Retina (Philadelphia, Pa.), 40(4), 735-742 (2019-01-15)
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Zizhong Hu et al.
Eye (London, England), 32(9), 1512-1518 (2018-05-31)
The purpose of this study is to investigate the effectiveness of a new surgical technique of non-inverted pedicle internal limiting membrane (ILM) transposition for the treatment of eyes with large macular hole. This is a retrospective, consecutive, interventional case series.
Samarium diiodide in tetrahydropyran: Preparation and some reactions in organic chemistry.
Namy NJ, et al.
Tetrahedron Letters, 35(11), 1723-1726 (1994)
Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation.
Lei Liu et al.
Angewandte Chemie (International ed. in English), 49(17), 3069-3072 (2010-03-24)

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