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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
Bp:
65-67 °C (lit.)
Vapor pressure:
114 mmHg ( 15 °C), 143 mmHg ( 20 °C)
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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

View returnable container options.

Other Notes

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

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3

signalword

Danger

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

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 Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT7264
SHBT6404
SHBT5257
SHBT4315
SHBT3442

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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)
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
Mauro Niso et al.
Chembiochem : a European journal of chemical biology, 16(7), 1078-1083 (2015-03-11)
Although sigma-2 (σ2 ) receptors are still enigmatic proteins, they are promising targets for tumor treatment and diagnosis. With the aim of clarifying their role in oncology, we developed a σ2 -selective fluorescent tracer (compound 5) as a specific tool
Maria Laura Pati et al.
BMC cancer, 17(1), 51-51 (2017-01-15)
Despite considerable efforts by scientific research, pancreatic cancer is the fourth leading cause of cancer related mortalities. Sigma-2 receptors, which are overexpressed in several tumors, represent promising targets for triggering selective pancreatic cancer cells death. We selected five differently structured
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Global Trade Item Number

SKUGTIN
186562-100ML04061838758217
186562-200L-P104061838151445
186562-200L-AM04061838161154
186562-200L-P204061838225917
186562-2L04061837531378
186562-400L-P104061838151476
186562-4X2L04061838758224
186562-IL-10L-BK04061838689917
186562-6X1L04061838758231
186562-1L04061837531361
186562-18L04061838151421
186562-12X100ML04061837531354
186562-200L-C0104061838151438
186562-208L04061838225924
186562-250ML04061837535611
186562-PS-200LP1NB04065267793078
186562-PZ04061823900270

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