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Diethyl ether

Base Information
  • Chemical Name:Diethyl ether
  • CAS No.:60-29-7
  • Deprecated CAS:74446-43-8,7578-39-4,927820-24-4,1480389-44-3,7578-39-4,927820-24-4
  • Molecular Formula:C4H10O
  • Molecular Weight:74.1228
  • Hs Code.:2909 11 00
  • European Community (EC) Number:200-467-2
  • ICSC Number:0355
  • NSC Number:100036
  • UN Number:1155
  • UNII:0F5N573A2Y
  • DSSTox Substance ID:DTXSID3021720
  • Nikkaji Number:J1.925I
  • Wikipedia:Diethyl ether
  • Wikidata:Q202218
  • NCI Thesaurus Code:C29819
  • RXCUI:1363043
  • Metabolomics Workbench ID:52129
  • ChEMBL ID:CHEMBL16264
  • Mol file:60-29-7.mol
Diethyl ether

Synonyms:Ether(6CI);Ethyl ether (8CI);1,1'-Oxybisethane;3-Oxapentane;Anaesthetic ether;Anesthesia ether;Anesthetic ether;Diethyl oxide;Ethoxyethane;Ethyl oxide;NSC 100036;Pronarcol;Sulfuric ether;Ethyl ether;Ethane, 1,1'-oxybis-;

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Diethyl ether
Chemical Property:
  • Appearance/Colour:Colourless liquid 
  • Vapor Pressure:28.69 psi ( 55 °C) 
  • Melting Point:-116 °C 
  • Refractive Index:n20/D 1.3530(lit.)  
  • Boiling Point:33.177 °C at 760 mmHg 
  • Flash Point:-45 °C 
  • PSA:9.23000 
  • Density:0.734 g/cm3 
  • LogP:1.04280 
  • Storage Temp.:Store at RT. 
  • Solubility.:Soluble in water, miscible with ethanol (96 per cent), with methylene chloride and with fatty oils. It is highly flammable. 
  • Water Solubility.:69 g/L (20 ºC) 
  • XLogP3:0.9
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:1
  • Rotatable Bond Count:2
  • Exact Mass:74.073164938
  • Heavy Atom Count:5
  • Complexity:11.1
  • Transport DOT Label:Flammable Liquid
Purity/Quality:
Safty Information:
  • Pictogram(s): HighlyF+, HarmfulXn, Toxic
  • Hazard Codes:F+,Xn,T,F 
  • Statements: 12-19-22-66-67-39/23/24/25-23/24/25-11 
  • Safety Statements: 9-16-29-33-45-36/37-7 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Solvents -> Ethers (
  • Canonical SMILES:CCOCC
  • Recent NIPH Clinical Trials:Effects of beraprost sodium sustained-release tablet on improvement of insulin resistance in patients with type 2 diabetes with obesity in a Double-Blinded, Randomized, Placebo-Controlled, Crossover Trial.
  • Inhalation Risk:A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
  • Effects of Short Term Exposure:The substance is irritating to the eyes and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system. This may result in narcosis.
  • Effects of Long Term Exposure:The substance defats the skin, which may cause dryness or cracking. The substance may have effects on the central nervous system. May cause addiction.
  • Description Diethyl ether is a component of starting fluids and is used as a solvent in the manufacture of synthetic dyes and plastics. Because of its characteristics, diethyl ether was widely used in many countries as an anesthetic agent, but was then replaced by other substances in the 1960s.
  • Physical properties Colorless, hygroscopic, volatile liquid with a sweet, pungent odor. Odor threshold concentration is 330 ppb (quoted, Keith and Walters, 1992).
  • Uses Ethyl ether is used as a solvent for fats, oils,waxes, gums, perfumes, and nitrocellulose;in making gun powder; as an anesthetic; andin organic synthesis. Ether was applied topically, inhaled, and consumed for medical purposes well before it was used as an anesthetic. Ether is only slightly soluble in water (6.9%), but it is a good solvent for nonpolar organic compounds. Approximately 65% of ether production is used as a solvent for waxes, fats, oils, gums, resins, nitrocellulose, natural rubber, and other organics. As a solvent, it is used as an extracting agent for plant and animal compounds in the production of pharmaceuticals and cosmetics. Another 25% of total ether production is used in chemical synthesis. It is an intermediate used in the production of monoethanolamine (MEA, C2H7NO). Ether is used in the production of Grignard reagents. A Grignard reagent has the general form RMgX, where R is an alkyl or aryl group and X is a halogen. Grignard reagents are widely used in industrial organic synthesis. A Grignard reagent is typically made by reacting a haloalkane with magnesium in an ether solution, for example, CH3I + MgCH3MgI. Ether is a common starting fluid, especially for diesel engines. Diethyl ether has been used extensively as a general anesthetic. ethyl ether is a solvent that may cause skin irritation. Although considered a non-comedogenic raw material, it is rarely used in cosmetics. Solvent for waxes, fats, oils, perfumes, alkaloids, gums. Excellent solvent for nitrocellulose when mixed with alcohol. Important reagent in organic syntheses, especially in Grignard and Wurtz type reactions. Easily removable extractant of active principles (hormones, etc.) from plant and animal tissues. In the manufacture of gun powder. As primer for gasoline engines.
Technology Process of Diethyl ether

There total 692 articles about Diethyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With copper dichloride; for 24h; Product distribution; Ambient temperature; other reagent;
Guidance literature:
With deficient carbonate-containing hydroxyapatites (HapD); at 400 ℃; Overall yield = 62.1 %; Catalytic behavior; Inert atmosphere;
DOI:10.1039/c5cy00327j
Guidance literature:
With stoichiometric carbonate-containing hydroxyapatites (Hap); at 400 ℃; Overall yield = 65.1 %; Catalytic behavior; Inert atmosphere;
DOI:10.1039/c5cy00327j
Refernces

Ruthenium complexes bearing N-H acidic pyrazole ligands

10.1002/ejic.201000802

The study focuses on the synthesis and investigation of ruthenium complexes bearing N-H acidic pyrazole ligands and their application in catalytic hydrogenation reactions. The researchers treated chelate ligands containing pyrazole groups with various ruthenium precursors to form complexes with protic N-H groups near the catalytically active ruthenium center. These complexes were characterized by spectroscopic methods and DFT calculations, and their structure and reactivity were analyzed. The study aimed to understand the role of the acidic N-H groups in metal-ligand-bifunctional hydrogenation, where a hydrido ligand and a proton from a protic group are transferred simultaneously. The catalytic performance of these complexes was evaluated through the hydrogenation and transfer hydrogenation of acetophenone, and the results were connected to the ligand's electronic and structural properties. The research provides insights into the design of efficient catalysts for hydrogenation reactions by leveraging the acidic N-H groups in pyrazole ligands.

Synthesis of Two 2,2′-Bipyridine Containing Macrocycles for the Preparation of Interlocked Architectures

10.1071/CH16710

The study reports on the successful synthesis and characterization of two 28-membered, 2,2'-bipyridine-containing macrocycles in high yield. The first macrocycle was formed through a Williamson ether synthesis, and upon reduction with sodium borohydride, the second macrocycle was produced quantitatively. These macrocycles, which contain a 2,2'-bipyridine unit, are potentially useful components for creating a variety of interlocked architectures, including catenanes, rotaxanes, and molecular machines. The research builds upon previous work by Sauvage, Stoddart, and Feringa, who were awarded the 2016 Nobel Prize in Chemistry for their contributions to the design and synthesis of molecular machines, and it aims to improve upon the yield-limiting macrocyclisation reactions that have historically been a challenge in the field. The study also discusses the use of high-yielding synthetic strategies and the potential for future investigations into the metal-complexation properties of these ligands and their application in forming interlocked structures.

SYNTHESIS AND STRUCTURE OF LARGE RING 2-PHENYLCYCLOALKANONES AND 2,n-DIPHENYLCYCLOALKANONES

10.1016/S0040-4039(00)85034-0

The research aimed to synthesize and determine the structure of large ring 2-prenylcycloalkanones and 2,n-diprenylcyclic ketones. The purpose of this study was to create a series of novel 2,n-diphenylcycloalkanones for photochemical studies on large ring cycloalkanones. The researchers successfully prepared these compounds in good yield by treating the corresponding 2,n-dibromocycloalkanone with LiCuPh2, a lithium diphenylcuprate reagent. The study reported single-crystal X-ray structures for cis- and trans-2,12-diphenylcyclododecanone, indicating the successful synthesis and structural characterization of these compounds. The chemicals used in the process included 2,n-dibromocycloalkanones, lithium diphenylcuprate (LiCuPh2), anhydrous ether, hexane, methanol (MeOH) for quenching, and various solvents for extraction and purification steps. The study concluded that the method could be adapted for mono- and diphenylation of cycloalkanones, and the yields and structures of the products were reported in detail.

Deblocking of dithioacetals and oxathioacetals using periodic acid under mild nonaqueous conditions

10.1016/0040-4039(96)00838-6

This research introduces a novel method for deblocking dithioacetals and oxathioacetals to their corresponding carbonyl compounds using periodic acid under mild nonaqueous conditions. The purpose of the study was to develop an efficient and mild deblocking method suitable for complex and acid-sensitive compounds, which is a significant challenge in organic synthesis. The researchers found that periodic acid in anhydrous solvents, such as ether and THF, effectively cleaved dithioacetals and oxathioacetals to yield aldehydes and ketones with high yields and chemoselectivity. Key chemicals used in the study included various dithioacetals, oxathioacetals, and periodic acid. The method's advantages include operational simplicity, short reaction times, and the absence of thiol odors post-reaction, making it particularly suitable for large-scale preparations. The study concluded that this nonaqueous periodic acid method is a significant addition to existing deblocking methodologies, offering versatility and ease of use for a wide range of substrates.

Formation and structural characterization of a five-membered zirconacycloallenoid

10.1039/c3dt51497h

The study focuses on the formation and structural characterization of a five-membered zirconacycloallenoid, a type of metallocene complex, through the reaction of a conjugated enyne with in situ generated zirconocene. The resulting compound was thoroughly analyzed using X-ray diffraction, revealing its unique structure and bonding characteristics. The research also explored the compound's reactivity, demonstrating its distinct behavior in reactions with additional zirconocene and acetonitrile, leading to the formation of different complexes. This work not only provides detailed insights into the structure and properties of metallacycloallenoid complexes but also uncovers new chemical reactions and potential applications in organometallic chemistry.

Synthetic precursors for TCNQF42a- compounds: Synthesis, characterization, and electrochemical studies of (Pr 4N)2TCNQF4 and Li2TCNQF4

10.1021/jo301403v

The study focuses on the synthesis, characterization, and electrochemical investigation of TCNQF4 2? compounds, specifically (Pr4N)2TCNQF4 and Li2TCNQF4. Researchers controlled the reaction stoichiometry and conditions to synthesize both LiTCNQF4 and Li2TCNQF4, with the latter being a significant achievement as it represents the first large-scale chemical synthesis of Li2TCNQF4. The chemicals used in the study included LiI, TCNQF4, acetonitrile, Pr4NBr, and various solvents such as diethyl ether, methanol, and acetone. These chemicals served to react and form the desired TCNQF4 2? salts, which were then characterized using UV?vis, FT-IR, Raman, and NMR spectroscopy, as well as high-resolution electrospray ionization mass spectrometry and electrochemistry. The synthesized compounds are valuable precursors for the synthesis of derivatives of the dianions and can be used to create metal and organic-based materials with potential applications in electronics and materials science.

Improved Procedure for Preparation of t-Alkyl Aryl Ethers

10.1055/s-1982-29739

The research aimed to improve the procedure for the preparation of t-alkyl aryl ethers, which are compounds for which synthesis methods in the literature are scarce and complex. The main challenge in synthesizing these compounds is the occurrence of side reactions, such as elimination reactions of the starting r-alkyl halide in basic media or rearrangements of the final product to C-alkylated phenols under acid conditions. The researchers reported a convenient modification of the existing procedure using nickel bisacetylacetonate as a catalyst and sodium hydrogen carbonate as a hydrogen chloride acceptor. This method was applied to various phenols and r-alkyl chlorides to produce t-alkyl aryl ethers with yields and conversions summarized in a table. The study concluded that the procedure was not effective for phenols with strong electron-withdrawing substituents and that ortho-substituted phenols reacted sluggishly, leading to variable amounts of rearranged products. The chemicals used in the process included phenols, r-alkyl chlorides, nickel acetylacetonate, sodium hydrogen carbonate, and diethyl ether, among others.

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