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Merck

186562

Tetrahydrofuran

≥99.9%, anhydrous, contains 250 ppm BHT as inhibitor

Synonym(s):

THF, Butylene oxide, Oxolane, Tetramethylene oxide

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About This Item

Empirical Formula (Hill Notation):
C4H8O
CAS Number:
109-99-9
Molecular Weight:
72.11
NACRES:
NA.21
PubChem Substance ID:
57647757
UNSPSC Code:
12191501
EC Number:
203-726-8
MDL number:
MFCD00005356
Beilstein/REAXYS Number:
102391
Assay:
≥99.9%
Grade:
anhydrous
Vapor pressure:
114 mmHg ( 15 °C), 143 mmHg ( 20 °C)

Key Documents

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Product Name

Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%

grade

anhydrous

Quality Level

200

vapor pressure

114 mmHg ( 15 °C), 143 mmHg ( 20 °C)

assay

≥99.9%

form

liquid

autoignition temp.

610 °F

contains

250 ppm BHT as inhibitor

expl. lim.

1.8-11.8 %

impurities

≤0.005% peroxides (as H2O2), <0.002% water (All units except 100 mL), <0.005% water (100 mL pkg)

pH

~7

mp

−108 °C (lit.)

solubility

H2O: soluble

density

0.889 g/mL at 25 °C (lit.)

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General description

Tetrahydrofuran (THF) is a saturated cyclic ether mainly used as an organic solvent. On long term storage it forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for the peroxide formation. It constitutes the key fragment of various natural products (polyether antibiotics). THF forms double hydrate with hydrogen sulfide, crystal structure of this double hydrate has been investigated by three-dimensional single-crystal studies.

Application

Dry tetrahydrofuran (THF) has been used in the synthesis of dichloro{bis[1,1′,1′′-(phosphinetriyl)tripiperidine]}palladium [(P(NC5H10)3)2Pd(Cl)2], which is widely used in the Heck reaction as a catalyst. It has been employed in the reaction medium of the Heck cross-coupling reaction of various aryl bromides and olefins.

Packaging

View returnable container options.

Other Notes

Greener alternatives are available for many THF applications, 2-Methyltetrahydrofuran (414247) and Cyclopentyl methyl ether (675970)

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

-6.2 °F - closed cup

flash_point_c

-21.2 °C - closed cup

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 1 petroleums + Hazardous rank II + Water soluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

186562-PZ: + 186562-12X100ML:4548173111742 + 186562-18L:4548173111759 + 186562-2L:4548173111780 + 186562-RSAMPLE: + 186562-400L-P1: + 186562-6X1L:4548173111810 + 186562-900ML: + 186562-20L: + 186562-200L-P1: + 186562-200L:4548173111773 + 186562-200L-C01: + 186562-VAR: + 186562-PR-200L-P2: + 186562-BULK: + 186562-200L-P2: + 186562-200L-P1BB: + 186562-PS-200LP1NB: + 186562-200L-AM: + 186562-IL-10L-BK: + 186562-208L: + 186562-250ML: + 186562-50L-P2: + 186562-56L:4548173111803 + 186562-400L-KL: + 186562-100ML:4548173111735 + 186562-4X2L:4548173111797 + 186562-1L:4548173111766 + 186562-25L:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8048
STBK9465
STBK8039
STBK8046
STBK8049

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro {bis [1, 1', 1''-(phosphinetriyl) tripiperidine]} palladium Under Mild Reaction Conditions.
Oberholzer M and Frech CM
Journal of Visualized Experiments, 85, e51444-e51444 (2014)
Carmen Abate et al.
Journal of medicinal chemistry, 57(8), 3314-3323 (2014-04-05)
Despite the promising potentials of σ2 receptors in cancer therapy and diagnosis, there are still ambiguities related to the nature and physiological role of the σ2 protein. With the aim of providing potent and reliable tools to be used in
Maria Laura Pati et al.
Pharmacological research, 117, 67-74 (2016-12-23)
A controversial relationship between sigma-2 and progesterone receptor membrane component 1 (PGRMC1) proteins, both representing promising targets for the therapy and diagnosis of tumors, exists since 2011, when the sigma-2 receptor was reported to be identical to PGRMC1. Because a
Francesco Berardi et al.
Journal of medicinal chemistry, 52(23), 7817-7828 (2009-10-22)
sigma(2)-Agonist 1-cyclohexyl-4-[3-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)propyl]piperazine (7, PB 28), which proved to revert doxorubicin resistance in breast cancer cells, was taken as a template to prepare new analogs. One of the two basic N-atoms was alternatively replaced by a methine or converted into an
Polyhedral clathrate hydrates. X. Structure of the double hydrate of tetrahydrofuran and hydrogen sulfide.
Mak TCW, et al.
J. Chem. Phys., 42(8), 2732-2737 (1965)
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