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Names | |
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Preferred IUPAC name Phenylacetic acid | |
Systematic IUPAC name 2-Phenylethanoic acid | |
Other names α-Toluic acid Benzeneacetic acid 2-Phenylacetic acid β-Phenylacetic acid | |
Identifiers | |
3D model (JSmol) | |
3DMet | |
1099647 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.002.862 |
EC Number |
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68976 | |
KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C8H8O2 | |
Molar mass | 136.15 g/mol |
Appearance | white solid |
Odor | honey-like |
Density | 1.0809 g/cm3 |
Melting point | 76 to 77 °C (169 to 171 °F; 349 to 350 K) |
Boiling point | 265.5 °C (509.9 °F; 538.6 K) |
15 g/L | |
Acidity (pKa) | 4.31 (H2O) [1] |
-82.72·10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
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Danger | |
H318, H319 | |
P264, P280, P305+P351+P338, P310, P337+P313 | |
NFPA 704 (fire diamond) | |
Safety data sheet (SDS) | External MSDS |
Legal status | |
Related compounds | |
Related compounds | Benzoic acid, Phenylpropanoic acid, Cinnamic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Phenylacetic acid (conjugate base phenylacetate), also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China. [3]
Phenylacetic acid has been found to be an active auxin (a type of plant hormone), [4] found predominantly in fruits. However, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid. In addition the molecule is naturally produced by the metapleural gland of most ant species and used as an antimicrobial. It is also the oxidation product of phenethylamine in humans following metabolism by monoamine oxidase and subsequent metabolism of the intermediate product, phenylacetaldehyde, by the aldehyde dehydrogenase enzyme; these enzymes are also found in many other organisms.
This compound may be prepared by the hydrolysis of benzyl cyanide: [5] [6]
Phenylacetic acid undergoes ketonic decarboxylation to form ketones. [7] It can be condensed with itself to form dibenzyl ketone, or with a large excess of another carboxylic acid (in the form of an acid anhydride), such as with acetic anhydride to form phenylacetone.
Phenylacetic acid is used in some perfumes, as it possesses a honey-like odor even in low concentrations. It is also used in penicillin G production and diclofenac production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then excreted from the patient's body. It's also used in the illicit production of phenylacetone, which is used in the manufacture of methamphetamine.
The sodium salt of phenylacetic acid, sodium phenylacetate, is used as a pharmaceutical drug for the treatment of urea cycle disorders, including as the combination drug sodium phenylacetate/sodium benzoate (Ammonul). [8]
Phenylacetic acid is used in the preparation of and derived from several pharmaceutical drugs, including camylofin, bendazol, triafungin, phenacemide, lorcainide, phenindione, phenelzine and cyclopentolate.[ citation needed ]
In the crime drama Breaking Bad , phenylacetic acid is featured twice as a precursor to methamphetamine, first in the episode titled "A No-Rough-Stuff-Type Deal", then in "Salud". [9]
Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
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. These compounds contain a distinctive functional 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.
In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.
In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.
In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Clandestine chemistry is chemistry carried out in secret, and particularly in illegal drug laboratories. Larger labs are usually run by gangs or organized crime intending to produce for distribution on the black market. Smaller labs can be run by individual chemists working clandestinely in order to synthesize smaller amounts of controlled substances or simply out of a hobbyist interest in chemistry, often because of the difficulty in ascertaining the purity of other, illegally synthesized drugs obtained on the black market. The term clandestine lab is generally used in any situation involving the production of illicit compounds, regardless of whether the facilities being used qualify as a true laboratory.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.
Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.
In organic chemistry, ozonolysis is an organic reaction where the unsaturated bonds are cleaved with ozone. Multiple carbon–carbon bond are replaced by carbonyl groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being oxidized and the work-up conditions.
An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O))2O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. Thus, (CH3CO)2O is called acetic anhydride.Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").
The United States Drug Enforcement Administration (DEA) maintains lists regarding the classification of illicit drugs. It also maintains List I of chemicals and List II of chemicals, which contain chemicals that are used to manufacture the controlled substances/illicit drugs. The list is designated within the Controlled Substances Act but can be modified by the U.S. Attorney General as illegal manufacturing practices change.
Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.
Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ortho-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic functional groups, the compound is amphoteric. Anthranilic acid is a white solid when pure, although commercial samples may appear yellow. The anion [C6H4(NH2)(CO2)]−, obtained by the deprotonation of anthranilic acid, is called anthranilate. Anthranilic acid was once thought to be a vitamin and was referred to as vitamin L1 in that context, but it is now known to be non-essential in human nutrition.
Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic. For this reason, dibenzyl ketone is frequently used in an aldol condensation reaction with benzil and base to create tetraphenylcyclopentadienone. Vera Bogdanovskaia is credited with the classification of dibenzyl ketone.
α-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C15H12O2 and appears as an off-white crystalline solid.
European law on illicit drug precursors:
Drug precursors, also referred to as precursor chemicals or simply precursors, are substances used to manufacture illicit drugs. Most precursors also have legitimate commercial uses and are legally used in a wide variety of industrial processes and consumer products, such as medicines, flavourings, and fragrances.
Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (−C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.