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186562

Sigma-Aldrich

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
Beilstein/REAXYS Number:
102391
EC Number:
203-726-8
MDL number:
MFCD00005356
UNSPSC Code:
12191501
PubChem Substance ID:
57647757
NACRES:
NA.21
Grade:
anhydrous
Assay:
≥99.9%
Bp:
65-67 °C (lit.)
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 density

2.5 (vs air)

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)

refractive index

n20/D 1.407 (lit.)

pH

~7

bp

65-67 °C (lit.)

mp

−108 °C (lit.)

solubility

H2O: soluble

density

0.889 g/mL at 25 °C (lit.)

SMILES string

C1CCOC1

InChI

1S/C4H8O/c1-2-4-5-3-1/h1-4H2

InChI key

WYURNTSHIVDZCO-UHFFFAOYSA-N

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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

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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_germany

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8046
STBK8049
STBK8048
STBK9465
STBK8039

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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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