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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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Baoling Lai et al.
Developmental neurobiology, 78(9), 859-872 (2018-07-20)
The cyclic nucleotide cGMP is an intracellular second messenger with important roles in neuronal functions and animals' behaviors. The phosphodiesterases (PDEs) are a family of enzymes that hydrolyze the second messengers cGMP and cAMP. Inhibition of phosphodiesterase 9 (PDE9), a
Zhaotian Zhang et al.
International ophthalmology, 39(7), 1543-1551 (2018-06-24)
To introduce novel and easy techniques for 27-gauge silicone oil (SO) infusion and removal. Consecutive patients treated with 27-gauge pars plana vitrectomy (PPV) plus SO infusion (Infusion Group) and scheduled to have SO removal (Removal Group) were prospectively included, respectively.
Flame chemistry of tetrahydropyran as a model heteroatomic biofuel.
Labbe NJ, et al.
Proceedings of the Combustion Institute, 34(3), 259-267 (2013)
Veysel Cankurtaran et al.
Bosnian journal of basic medical sciences, 17(1), 74-80 (2017-01-31)
Retinal detachment is the separation of the sensory retina from the retinal pigment epithelium by subretinal fluid. There are several types of retinal re-attachment surgery, including scleral buckling (SB), pneumatic retinopexy, and vitrectomy (with or without SB). The objective of
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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