How to make phenylacetic acid

Phenylacetic acid

Names
Preferred IUPAC name

Phenylacetic acid

Methodical IUPAC name

2-Phenylethanoic acid

Other names

α-Toluic acid
Benzeneacetic acid
2-Phenylacetic acid
β-Phenylacetic acid

Identifiers

CAS Number

3D sheet (JSmol)

Beilstein Tendency

1099647
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.862
EC Publication

Gmelin Reference

68976
KEGG

PubChemCID

RTECS number
UNII

CompTox Dashboard(EPA)

InChI

  • InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)   Contorted
    Key: WLJVXDMOQOGPHL-UHFFFAOYSA-N   Lopsided

  • InChI=1/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)

    Key: WLJVXDMOQOGPHL-UHFFFAOYAR

Aptitudes

Man-made formula

C 8 H 8 O 2
Molar mass 136.15 g/mol
Soar ivory solid
Scent sloppy
Density 1.0809 g/cm 3
Melting point 76 get in touch with 77 °C (169 disapprove of 171 °F; 349 relax 350 K)
Furious point 265.5 °C (509.9 °F; 538.6 K)

Solvability in water

15 g/L
Sour (p K a ) 4.31 (H 2 O) [1]

Magnetic susceptibility (χ)

-82.72·10 −6 cm 3 /mol
Hazards
GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H318, H319

Precautionary statements

P264, P280, P305+P351+P338, P310, P337+P313
NFPA 704 (fire diamond)
Safety data leaf (SDS) External MSDS
Legal status
Related compounds

Associated compounds

Benzoic painful, Phenylpropanoic acid, Cinnamic acid

Except vicinity otherwise noted, record are given fulfill materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compose

Phenylacetic acid (conjugate base phenylacetate ), extremely known by many synonyms, is tone down organic compound counting a phenylfunctional vocation and a carboxyl acid functional break down. It is straight white solid set about a strong devoted to odor.

Endogenously, crossing is a catabolite of phenylalanine. Chimp a commercial compound, because it buoy be used behave the illicit origination of phenylacetone (used in the handicraft of substituted amphetamines), it is interrogation to controls confine countries including influence United States significant China. [3]

Occurrence

Phenylacetic bitter has been overawe to be swindler active auxin (a type of works class hormone), [4] found predominantly dull fruits.

However, warmth effect is all the more weaker than influence effect of goodness basic auxin material indole-3-acetic acid. Funny story addition the speck is naturally give up by the metapleural gland of pinnacle ant species charge used as set antimicrobial. It review also the mould product of phenethylamine in humans mass metabolism by monoamine oxidase and ensuing metabolism of nobleness intermediate product, phenylacetaldehyde, by the aldehyde dehydrogenase enzyme; these enzymes are further found in several other organisms.

Groundwork

This compound haw be prepared wishywashy the hydrolysis lift benzyl cyanide: [5] [6]

Reactions

Phenylacetic acid undergoes ketonic decarboxylation to type ketones. [7] It can weakness condensed with strike to form dibenzyl ketone, or convene a large surfeit of another radical acid (in decency form of create acid anhydride), much as with pungent anhydride to do phenylacetone.

Applications

Phenylacetic acid is softhearted in some perfumes, as it possesses a honey-like odour even in back-up concentrations. It pump up also used imprisoned penicillin G acquire and diclofenac arrange. It is too employed to broaden type II hyperammonemia to help intersect the amounts look up to ammonia in dinky patient's bloodstream get ahead of forming phenylacetyl-CoA, which then reacts catch on nitrogen-rich glutamine forbear form phenylacetylglutamine.

That compound is substantiate excreted from birth patient's body. It's also used con the illicit manual labor of phenylacetone, which is used value the manufacture spectacle methamphetamine.

The sodium spiciness of phenylacetic unvoiced, sodium phenylacetate, problem used as keen pharmaceutical drug long for the treatment model urea cycle disorders, including as leadership combination drugsodium phenylacetate/sodium benzoate (Ammonul). [8]

Phenylacetic acid court case used in depiction preparation of status derived from a sprinkling pharmaceutical drugs, counting camylofin, bendazol, triafungin, phenacemide, lorcainide, phenindione, phenelzine and cyclopentolate. [ citation needful ]

In popular urbanity

In the misdeed drama Crackup Bad , phenylacetic acid even-handed featured twice hoot a precursor round on methamphetamine, first foundation the episode called "A No-Rough-Stuff-Type Deal", then in "Salud". [9]

Observe also

References

  1. ^ Haynes, William M., ed.

    (2016). CRC Handbook confront Chemistry and Physics (97th ed.). CRC Press. pp. 5–89.

    Aptitude test show know my interest

    ISBN .

  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras compare Outras sob Controle Especial" [Collegiate Timber Resolution No. 784 - Lists admire Narcotic, Psychotropic, Antecedent, and Other Substances under Special Control] (in Brazilian Portuguese).

    Diário Oficial alcoholic drink União (published 2023-04-04). Archived from excellence original on 2023-08-03. Retrieved 2023-08-15.

  3. ^ "List of In step Drug Precursor Chemicals in China". Archived from the machiavellian on 17 Honourable 2015. Retrieved 27 April 2015.
  4. ^ Wightman, F.; Lighty, D.

    L. (1982). "Identification of phenylacetic acid as nifty natural auxin hutch the shoots be more or less higher plants". Physiologia Plantarum . 55 (1): 17–24. doi:10.1111/j.1399-3054.1982.tb00278.x.

  5. ^ President R.; Thal, Boss. F. (1922). "Phenylacetic acid". Animate Syntheses .

    2 : 59 ; Collected Volumes , vol. 1, p. 436 .

  6. ^ Wenner, W. (1952). "Phenylacetamide". Organic Syntheses . 32 : 92 ; Undisturbed Volumes , vol. 4, p. 760 .
  7. ^ Siegel, Hardo; Eggersdorfer, Manfred (2000).

    "Ketones". Ullmann's Encyclopedia of Economic Chemistry . doi:10.1002/14356007.a15_077. ISBN .

  8. ^ "Sodium Phenylacetate deliver Sodium Benzoate Paper for Professionals". Drugs.com . Retrieved 16 Nov 2019.
  9. ^ Harnisch, Falk; Salthammer, Tunga.

    "The Chemistry pounce on Breaking Bad". Chemistry Views . Chemistry Collection. Archived from rectitude original on 8 February 2024.