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296082 Sigma-Aldrich

Diethyl ether

contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%

Synonym: Ether, Ethyl ether

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Properties

Related Categories Anhydrous, Anhydrous Solvents, Diethyl Ether, Products, Returnable Containers,
grade   anhydrous
vapor density   2.6 (vs air)
vapor pressure   28.66 psi ( 55 °C)
  8.56 psi ( 20 °C)
assay   ≥99.7%
autoignition temp.   320 °F
contains   1 ppm BHT as inhibitor
expl. lim.   36.5 %
impurities   <0.003% water
  <0.005% water (100 mL pkg)
evapn. residue   <0.0003%
refractive index   n20/D 1.3530(lit.)
bp   34.6 °C(lit.)
  34.6 °C
mp   −116 °C(lit.)
density   0.706 g/mL at 25 °C(lit.)

Description

Packaging

1, 6×1 L in Sure/Seal™

View returnable container options.

100, 12×100 mL in Sure/Seal™

18 L in Pure-Pac™ 1

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
May form explosive peroxides., Repeated exposure may cause skin dryness or cracking.
RIDADR 
UN 1155 3 / PGI
WGK Germany 
1
RTECS 
KI5775000
Flash Point(F) 
-38.2 °F
Flash Point(C) 
-39 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

A New Biarylphosphine Ligand for the Pd-Catalyzed Synthesis of Diaryl Ethers under Mild Conditions

An efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand�1. Heteroaryl halides, and f...
Keywords: Chromatography, Flash chromatography, Ligands

A New Palladium Precatalyst Allows for the Fast Suzuki-Miyaura Coupling Reactions of Unstable Polyfluorophenyl and 2-Heteroaryl Boronic Acids

A method for the Pd-catalyzed coupling of 2-aminothiazole derivatives with aryl bromides and triflates is described. Significantly, for this class of nucleophiles, the coupling exhibits a broad subst...
Keywords: Catalysis, Chromatography

Copper-Free Sonogashira Coupling of Cyclopropyl Iodides with Terminal Alkynes

An efficient palladium-catalyzed cyanation of aryl chlorides is established. In the presence of a highly effective Pd/CM-phos catalyst, cyanation of aryl chlorides proceeds at 71 �C in general, which...
Keywords: Catalysis, Chromatography, Column chromatography, Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy

Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

Good to excellent yields�of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd...
Keywords: Agrochemicals, Catalysis, Pharmaceutical

Determination of Water Content in Diethyl ether Using Karl Fischer Titration

Ethers behave similarly to hydrocarbons. They are mostly adequately soluble in methanol. Only long chain ethers require the addition of propanol or chloroform as solubilizers. Double bonds can someti...
Keywords: Pharmaceutical, Titrations

Palladium/Tris(tert-butyl)phosphine-Catalyzed Suzuki Cross- Couplings in the Presence of Water

The Suzuki reaction is an exceptionally useful cross-coupling process that has been widely applied in synthetic chemistry, and boronic acids are, by far, the most commonly employed coupling partner. ...
Keywords: Chromatography, Column chromatography, Cross couplings, Eliminations, Oxidative additions, Suzuki reactions

Pd-PEPPSI-IPent: An Active, Sterically Demanding Cross-Coupling Catalyst and Its Application in the Synthesis of Tetra-Ortho- Substituted Biaryls-

The halogenated 1H-1,2,4-triazole glycosides 6-11 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4- triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), ...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Glycosylations, Purification, Separation

Pd-PEPPSI-IPent: Low-Temperature Negishi Cross-Coupling for the Preparation of Highly Functionalized, Tetra-ortho-Substituted Biaryls-

A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readil...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Purification

The First Applications of Carbene Ligands in Cross-Couplings of Alkyl Electrophiles: Sonogashira Reactions of Unactivated Alkyl Bromides and Iodides

The synthesis of ?,?-alkynyl esters and amides using air-stable potassium alkynyltrifluoroborates as nucleophilic partners in a mild Suzuki-Miyaura cross-coupling reaction has been achieved. Propargy...
Keywords: Chromatography, Column chromatography, Coupling reactions, Cross couplings

The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides

A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were ...
Keywords: Chromatography, Flash chromatography

Peer-Reviewed Papers

References

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Protective effects of scutellarin on type II diabetes mellitus-induced testicular damages related to reactive oxygen species/Bcl-2/Bax and reactive oxygen species/microcirculation/staving pathway in diabetic rat. Long L, Wang J, Lu X, et al. J. Diabetes Res. 2015, 252530, (2015)

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Qualitative and quantitative determination of peptides related to celiac disease in mixtures derived from different methods of simulated gastrointestinal digestion of wheat products. Prandi B, Faccini A, Tedeschi T, et al. Anal. Bioanal. Chem 406(19), 4765-75, (2014)

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Quantitation of Maillard reaction products in commercially available pet foods. van Rooijen C, Bosch G, van der Poel AF, et al. J. Agric. Food Chem. 62(35), 8883-91, (2014)

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Inhibition of angiogenesis by antioxidant micelles. Moriyama M, Metzger S, van der Vlies AJ, et al. Adv. Healthc. Mater. 4(4), 569-75, (2015)

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Reduction of molecular leaching from a gel matrix for the precisely controlled release of encapsulated molecules by light stimulus. Amamoto T, Santa T, Kato M, et al. Chem. Pharm. Bull. 62(7), 649-53, (2014)

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Effect of processing conditions on the organosulfides of shallot (Allium cepa L. Aggregatum group). Tocmo R, Lin Y, Huang D, et al. J. Agric. Food Chem. 62(23), 5296-304, (2014)

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Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides. Kong N, Shimpi MR, Ramström O, et al. Carbohydr. Res. 405, 33-8, (2015)

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Influence of polymer end-chemistry on the morphology of perfluorohexane polymeric microcapsules intended as ultrasound contrast agents. Mousnier L, Huang N, Morvan E, et al. Int. J. Pharm. 471(1-2), 10-7, (2014)

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Selective intracellular delivery of proteasome inhibitors through pH-sensitive polymeric micelles directed to efficient antitumor therapy. Quader S, Cabral H, Mochida Y, et al. J. Control. Release 188, 67-77, (2014)

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Cell surface modification with ssDNA-PEG-lipid for analysing intercellular interactions between different cells. Teramura Y Biomaterials 48, 119-28, (2015)

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Synthesis, structure-activity, and structure-stability relationships of 2-substituted-N-(4-oxo-3-oxetanyl) N-acylethanolamine acid amidase (NAAA) inhibitors. Vitale R, Ottonello G, Petracca R, et al. ChemMedChem 9(2), 323-36, (2014)

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Europium bis(dimethylsilyl)amides including mixed-valent Eu3[N(SiHMe2)2]6[?-N(SiHMe2)2]2. Bienfait AM, Schädle C, Maichle-Mössmer C, et al. Dalton Trans. 43(46), 17324-32, (2014)

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Control of Maillard-type off-flavor development in ultrahigh-temperature-processed bovine milk by phenolic chemistry. Kokkinidou S, Peterson DG, et al. J. Agric. Food Chem. 62(32), 8023-33, (2014)

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Characterization of in vitro metabolites of JWH-018, JWH-073 and their 4-methyl derivatives, markers of the abuse of these synthetic cannabinoids. Gambaro V, Arnoldi S, Bellucci S, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 957, 68-76, (2014)

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Formation of monodisperse hierarchical lipid particles utilizing microfluidic droplets in a nonequilibrium state. Mizuno M, Toyota T, Konishi M, et al. Langmuir 31(8), 2334-41, (2015)

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Analysis of beers from an 1840s' shipwreck. Londesborough J, Dresel M, Gibson B, et al. J. Agric. Food Chem. 63(9), 2525-36, (2015)

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5-HT7 receptor activation: procognitive and antiamnesic effects. Meneses A, Perez-Garcia G, Liy-Salmeron G, et al. Psychopharmacol. Ser. 232(3), 595-603, (2015)

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A mouse strain less responsive to dioxin-induced prostaglandin E2 synthesis is resistant to the onset of neonatal hydronephrosis. Aida-Yasuoka K, Yoshioka W, Kawaguchi T, et al. Toxicol. Sci. 141(2), 465-74, (2014)

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Metabolism of methylstenbolone studied with human liver microsomes and the uPA?/?-SCID chimeric mouse model. Geldof L, Lootens L, Polet M, et al. Biomed. Chromatogr. 28(7), 974-85, (2014)

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Cell patterning on polylactic acid through surface-tethered oligonucleotides. Matsui T, Arima Y, Takemoto N, et al. Acta Biomater. 13, 32-41, (2015)

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Variation of electronic transitions and reduction potentials of cerium(IV) complexes. Williams UJ, Schneider D, Dorfner WL, et al. Dalton Trans. 43(43), 16197-206, (2014)

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Highly protein-resistant coatings and suspension cell culture thereon from amphiphilic block copolymers prepared by RAFT polymerization. Haraguchi K, Kubota K, Takada T, et al. Biomacromolecules 15(6), 1992-2003, (2014)

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Lung deposition and cellular uptake behavior of pathogen-mimicking nanovaccines in the first 48 hours. Ross KA, Haughney SL, Petersen LK, et al. Adv. Healthc. Mater. 3(7), 1071-7, (2014)

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Glial ?-oxidation regulates Drosophila energy metabolism. Schulz JG, Laranjeira A, Van Huffel L, et al. Sci. Rep. 5, 7805, (2015)

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GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high Kanna isolated from Sceletium tortuosum. Meyer GM, Wink CS, Zapp J, et al. Anal. Bioanal. Chem 407(3), 761-78, (2015)

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Bioluminescent liquid light guide pad biosensor for indoor air toxicity monitoring. Eltzov E, Cohen A, Marks RS, et al. Anal. Chem. 87(7), 3655-61, (2015)

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A novel folic acid-conjugated TiO?-SiO? photosensitizer for cancer targeting in photodynamic therapy. Feng X, Zhang S, Wu H, et al. Colloids Surf. B Biointerfaces 125, 197-205, (2015)

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Cyclic avian mass mortality in the northeastern United States is associated with a novel orthomyxovirus. Allison AB, Ballard JR, Tesh RB, et al. J. Virol. 89(2), 1389-403, (2015)

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Acid sphingomyelinase activity is regulated by membrane lipids and facilitates cholesterol transfer by NPC2. Oninla VO, Breiden B, Babalola JO, et al. J. Lipid Res. 55(12), 2606-19, (2014)

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Low temperature-induced circulating triiodothyronine accelerates seasonal testicular regression. Ikegami K, Atsumi Y, Yorinaga E, et al. Endocrinology 156(2), 647-59, (2015)

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Receptor-mediated uptake of boron-rich neuropeptide y analogues for boron neutron capture therapy. Ahrens VM, Frank R, Boehnke S, et al. ChemMedChem 10(1), 164-72, (2014)

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Key changes in wine aroma active compounds during bottle storage of Spanish red wines under different oxygen levels. Ferreira V, Bueno M, Franco-Luesma E, et al. J. Agric. Food Chem. 62(41), 10015-27, (2014)

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A new analytical method to determine non-steroidal anti-inflammatory drugs in surface water using in situ derivatization combined with ultrasound-assisted emulsification microextraction followed by gas chromatography-mass spectrometry. Lee CH, Shin Y, Nam MW, et al. Talanta 129, 552-9, (2014)

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Rhythmic expression of cytochrome P450 epoxygenases CYP4x1 and CYP2c11 in the rat brain and vasculature. Carver KA, Lourim D, Tryba AK, et al. Am. J. Physiol. Cell Physiol. 307(11), C989-98, (2014)

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Role of oxidative stress in Sclerotial differentiation and aflatoxin B1 biosynthesis in Aspergillus flavus. Grintzalis K, Vernardis SI, Klapa MI, et al. Appl. Environ. Microbiol. 80(18), 5561-71, (2014)

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Newborn boys and girls differ in the lipid composition of vernix caseosa. Míková R, Vrkoslav V, Hanus R, et al. PLoS ONE 9(6), e99173, (2014)

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Synthesis, characterization and mechanistic-insight into the anti-proliferative potential of PLGA-gemcitabine conjugate. Khare V, Kour S, Alam N, et al. Int. J. Pharm. 470(1-2), 51-62, (2014)

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Photoinduced intercalation and coordination of a dirhodium complex to DNA: dual DNA binding. Palmer AM, Burya SJ, Gallucci JC, et al. ChemMedChem 9(6), 1260-5, (2014)

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Highly specific in vivo gene delivery for p53-mediated apoptosis and genetic photodynamic therapies of tumour. Tseng SJ, Liao ZX, Kao SH, et al. Nat. Commun. 6, 6456, (2015)

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Local pathology and systemic serum bupivacaine after subcutaneous delivery of slow-releasing bupivacaine microspheres. Schmidt B, Ohri R, Wang JC, et al. Anesth. Analg. 120(1), 36-44, (2015)

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Regulation of osteoclastogenesis through Tim-3: possible involvement of the Tim-3/galectin-9 system in the modulation of inflammatory bone destruction. Moriyama K, Kukita A, Li YJ, et al. Lab. Invest. 94(11), 1200-11, (2014)

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Qualitative and spatial metabolite profiling of lichens by a LC-MS approach combined with optimised extraction. Parrot D, Peresse T, Hitti E, et al. Phytochem. Anal. 26(1), 23-33, (2014)

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Nickel(II) complexes of pentadentate N5 ligands as catalysts for alkane hydroxylation by using m-CPBA as oxidant: a combined experimental and computational study. Sankaralingam M, Balamurugan M, Palaniandavar M, et al. Chemistry 20(36), 11346-61, (2014)

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In situ formation of H2O2 for P450 peroxygenases. Paul CE, Churakova E, Maurits E, et al. Bioorg. Med. Chem. 22(20), 5692-6, (2014)

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A Pseudomonas putida strain genetically engineered for 1,2,3-trichloropropane bioremediation. Samin G, Pavlova M, Arif MI, et al. Appl. Environ. Microbiol. 80(17), 5467-76, (2014)

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Cabergoline, dopamine D2 receptor agonist, prevents neuronal cell death under oxidative stress via reducing excitotoxicity. Odaka H, Numakawa T, Adachi N, et al. PLoS ONE 9(6), e99271, (2014)

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Controlled iontophoretic delivery of pramipexole: electrotransport kinetics in vitro and in vivo. Kalaria DR, Patel P, Merino V, et al. Eur. J. Pharm. Biopharm. 88(1), 56-63, (2014)

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Development and characterization of nanocarriers for topical treatment of psoriasis by using combination therapy. Parnami N, Garg T, Rath G, et al. Artif. Cells. Nanomed. Biotechnol. 42(6), 406-12, (2014)

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Antibacterial activity of enrofloxacin and ciprofloxacin derivatives of ?-octaarginine. Purkayastha N, Capone S, Beck AK, et al. Chem. Biodivers. 12(2), 179-93, (2015)

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Preservatives in cosmetics in the Israeli market conform well to the EU legislation. Horev L, Isaksson M, Engfeldt M, et al. J. Eur. Acad. Dermatol. Venereol. 29(4), 761-6, (2015)

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Merck 14,3806

Beil. 1,IV,1314

Aldrich MSDS 1, 864:B / Corp MSDS 1 (1), 1549:A / FT-IR 2 (1), 302:B / FT-IR 1 (1), 203:A / FT-NMR 1 (1), 317:A / IR-Spectra (3), 124:A / IR-Spectra (2), 114:A / NMR-Reference 2 (1), 173:A / RegBook 1 (1), 209:B / Sax 6, 1350 / Structure Index 1, 29:B:1 / Vapor Phase 3, 265:B

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