Ethyl phenyl ether

Last updated
Ethyl phenyl ether
Ethyl phenyl ether.png
Ethoxybenzene 3D ball.png
Names
Preferred IUPAC name
Ethoxybenzene
Other names
  • Phenetole
  • Phenoxyethane [1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.854 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3 Yes check.svgY
    Key: DLRJIFUOBPOJNS-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H10O/c1-2-9-8-6-4-3-5-7-8/h3-7H,2H2,1H3
    Key: DLRJIFUOBPOJNS-UHFFFAOYAS
  • O(c1ccccc1)CC
Properties
C8H10O
Molar mass 122.167 g·mol−1
AppearanceColorless to yellowish oily liquid [2]
Density 0.967 g/mL [2]
Melting point −30 °C (−22 °F; 243 K) [2]
Boiling point 169 to 170 °C (336 to 338 °F; 442 to 443 K) [2]
0.57 g/L [2]
Hazards
Flash point 57 °C (135 °F; 330 K) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethyl phenyl ether (or phenetole) is an organic compound that belongs to a class of compounds called ethers. Ethyl phenyl ether has the same properties as some other ethers, such as volatility, explosive vapors, and the ability to form peroxides. It will dissolve in less polar solvents such as ethanol or ether, but not in polar solvents such as water. [1]

Contents

Preparation

Ethyl phenyl ether can be prepared by the reaction of phenol with diethyl sulfate:

PhOH + NaOH → PhONa+
PhONa+ + Et2SO4 → Ph-O-Et

This reaction follows SN2 path.[ citation needed ]

See also

Notes

  1. 1 2 "Phenetole". PubChem. 26 March 2005. Retrieved 2022-08-22.
  2. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

Additional references


Related Research Articles

<span class="mw-page-title-main">Alcohol (chemistry)</span> Organic compound with at least one hydroxyl (–OH) group

In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol, to complex, like sucrose and cholesterol. The presence of an OH group strongly modifies the properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur.

<span class="mw-page-title-main">Ether</span> Organic compounds made of alkyl/aryl groups bound to oxygen (R–O–R)

In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two organyl groups. They have the general formula R−O−R′, where R and R′ represent organyl groups. Ethers can again be classified into two varieties: if the organyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether". Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

<span class="mw-page-title-main">Alkoxy group</span> Chemical group (R–O)

In chemistry, the alkoxy group is an alkyl group which is singularly bonded to oxygen; thus R−O. Denoted usually with apostrophe('). The range of alkoxy groups is vast, the simplest being methoxy. An ethoxy group is found in the organic compound ethyl phenyl ether.

<span class="mw-page-title-main">Anisole</span> Organic compound (CH₃OC₆H₅) also named methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

Adams' catalyst, also known as platinum dioxide, is usually represented as platinum(IV) oxide hydrate, PtO2•H2O. It is a catalyst for hydrogenation and hydrogenolysis in organic synthesis. This dark brown powder is commercially available. The oxide itself is not an active catalyst, but it becomes active after exposure to hydrogen whereupon it converts to platinum black, which is responsible for reactions.

<span class="mw-page-title-main">Sodium bis(trimethylsilyl)amide</span> Chemical compound

Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula NaN(Si 3)2. This species, usually called NaHMDS, is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups.

<span class="mw-page-title-main">Sodium ethoxide</span> Ionic compound made of a C2H5–O anion and a sodium cation

Sodium ethoxide, also referred to as sodium ethanolate, is the ionic, organic compound with the formula CH3CH2ONa, C2H5ONa, or NaOEt. It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. It is commonly used as a strong base.

<span class="mw-page-title-main">Phenyllithium</span> Chemical compound

Phenyllithium is an organometallic agent with the empirical formula C6H5Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute.

<span class="mw-page-title-main">Trimethylsilyl chloride</span> Organosilicon compound with the formula (CH3)3SiCl

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

In organic chemistry, a carbonate ester is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

<span class="mw-page-title-main">Triethyloxonium tetrafluoroborate</span> Chemical compound

Triethyloxonium tetrafluoroborate is the organic oxonium compound with the formula [(CH3CH2)3O]+[BF4]. It is often called Meerwein's reagent or Meerwein's salt after its discoverer Hans Meerwein. Also well known and commercially available is the related trimethyloxonium tetrafluoroborate. The compounds are white solids that dissolve in polar organic solvents. They are strong alkylating agents. Aside from the BF−4 salt, many related derivatives are available.

<span class="mw-page-title-main">Phenylmagnesium bromide</span> Chemical compound

Phenylmagnesium bromide, with the simplified formula C
6
H
5
MgBr
, is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph" synthon.

<span class="mw-page-title-main">Methyltrichlorosilane</span> Chemical compound

Methyltrichlorosilane, also known as trichloromethylsilane, is a monomer and organosilicon compound with the formula CH3SiCl3. It is a colorless liquid with a sharp odor similar to that of hydrochloric acid. As methyltrichlorosilane is a reactive compound, it is mainly used a precursor for forming various cross-linked siloxane polymers.

<span class="mw-page-title-main">Sodium phenoxide</span> Chemical Compound

Sodium phenoxide (sodium phenolate) is an organic compound with the formula NaOC6H5. It is a white crystalline solid. Its anion, phenoxide, also known as phenolate, is the conjugate base of phenol. It is used as a precursor to many other organic compounds, such as aryl ethers.

The Fleming–Tamao oxidation, or Tamao–Kumada–Fleming oxidation, converts a carbon–silicon bond to a carbon–oxygen bond with a peroxy acid or hydrogen peroxide. Fleming–Tamao oxidation refers to two slightly different conditions developed concurrently in the early 1980s by the Kohei Tamao and Ian Fleming research groups.

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. It has an ethereous odor. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

<span class="mw-page-title-main">Phenylsodium</span> Chemical compound

Phenylsodium C6H5Na is an organosodium compound. Solid phenylsodium was first isolated by Nef in 1903. Although the behavior of phenylsodium and phenyl magnesium bromide are similar, the organosodium compound is very rarely used.