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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:
142-68-7
Molecular Weight:
86.13
Beilstein/REAXYS Number:
102436
EC Number:
205-552-8
MDL number:
MFCD00006585
UNSPSC Code:
12352005
PubChem Substance ID:
57648359
NACRES:
NA.21

grade

anhydrous

Quality Level

100

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
GHS02

signalword

Danger

hcodes

H225

Hazard Classifications

Flam. Liq. 2

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

3.2 °F - closed cup

flash_point_c

-16 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP7491
SHBJ6605
SHBJ8467
SHBH9980
SHBF5064V

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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)
Phase behaviour of gas hydrates of carbon dioxide in the presence of tetrahydropyran, cyclobutanone, cyclohexane and methylcyclohexane.
Mooijer-Van DH, et al.
Fluid Phase Equilibria, 182(1), 97-110 (2001)
Angélica Quintero-Flórez et al.
Journal of agricultural and food chemistry, 65(36), 7900-7907 (2017-08-15)
Volatile compounds are responsible for some sensory characteristics of virgin olive oil (VOO); however, they have not been studied from a nutritional point view. In this work, the effect of the simulated digestion on VOO volatile compounds responsible for green
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