Phenylarsonic acid

Phenylarsonic acid

Chembox new
ImageFile = PhAsO3H2.png ImageSize = 100px
IUPACName = Phenylarsonic acid
OtherNames = Benzenearsonic acid PAA
Section1 = Chembox Identifiers
CASNo = 98-05-5
PubChem =
SMILES =


Section2 = Chembox Properties
Formula = C6H7AsO3
MolarMass = 202.05
Appearance = colourless solid
Density = 1.76 g/cm3
MeltingPt = 154–158° °C
BoilingPt =
Solubility = low

Section3 = Chembox Hazards
MainHazards = Toxic
FlashPt =
Autoignition =

Phenylarsonic acid is the chemical compound with the formula C6H5AsO(OH)2, commonly abbreviated PhAsO3H2. This colourless solid is an organic derivative of arsenic acid, AsO(OH)3, where one OH group has been replaced by a phenyl group. The compound is a buffering agent and a precursor to other organoarsenic compounds, some of which are used in animal nutrition, e.g. 4-hydroxy-3-nitrobenzenearsonic acid.

Preparation and structure

PhAsO3H2 can be prepared in several routes, but a common one entails treatment of phenyl diazonium salts with sodium arsenite (prepared from arsenious acid and base) in the presence of a copper(II) catalyst. [Bullard, R. H.; Dickey, J. B. “Phenylarsonic Acid” Organic Syntheses, Collected Volume 2, pages 494 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0494.pdf] :C6H5N2+ + NaAsO3H2 → C6H5AsO3H2 + Na+ + N2Related derivatives are prepared similarly. [Ruddy, A. W.; Starkey, E. B. “p-Nitrophenylarsonic Acid” Organic Syntheses, Collected Volume 3, pp. 665 (1955). http://www.orgsyn.org/orgsyn/pdfs/CV3P0665.pdf] It was first prepared by Michaelis and Loenser. [cite journal
title = Ueber nitrirte Phenylarsenverbindungen
author = A. Michaelis, H. Loesner
journal = Berichte der deutschen chemischen Gesellschaft
volume = 27
issue =
pages = 263–272
year = 1877
url =
doi = 10.1002/cber.18940270151
] [cite journal
title = Ueber aromatische Arsenverbindungen
author = A. Michaelis
journal = Berichte der deutschen chemischen Gesellschaft
volume = 8
issue =
pages = 1316–1317
year = 1875
url =
doi = 10.1002/cber.187500802125
] [cite journal
title = Ueber die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Dritte Abhandlung: Ueber aromatische Arsenverbindungen
author = A. Michaelis, W. La Coste, A. Michaelis
journal = Annalen der Chemie
volume = 201
issue = 2-3
pages = 184–261
year = 1880
url =
doi = 10.1002/jlac.18802010204
] X-ray crystallography indicates that the molecules are connected by hydrogen-bonds consistent with short distance of 2.5 Å separating the oxygen atoms. The arsenic center is tetrahedral. [Struchkov, Yu T. “Crystal and molecular structure of phenylarsonic acid” Russian Chemical Bulletin 1960, Volume 9, 1829-1833. DOI|10.1007/BF00907739]

Related phenylarsonic acids

Several derivatives of phenylarsonic acid have been used as additives for animal feeds. These include 4-hydroxy-3-nitrobenzenearsonic acid (3-NHPAA, or Roxarsone), "p"-arsanilic acid ("p"-ASA), 4-nitrophenylarsonic acid (4-NPAA), and "p"-ureidophenylarsonic acid ("p"-UPAA).

References

External links


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • phenylarsonic acid — benzenarsonrūgštis statusas T sritis chemija formulė C₆H₅AsO₃H₂ atitikmenys: angl. benzenearsonic acid; phenylarsonic acid rus. бензоларсоновая кислота; фениларсоновая кислота ryšiai: sinonimas – fenilarsonrūgštis …   Chemijos terminų aiškinamasis žodynas

  • 4-Hydroxy-3-nitrobenzenearsonic acid — Chembox new ImageFile = Roxarsone.png ImageSize = 150px IUPACName = 4 Hydroxy 3 nitrobenzenearsonic acid OtherNames = Roxarson Roxarsone 2 Nitrophenol 4 arsonic acid Section1 = Chembox Identifiers CASNo = 121 19 7 PubChem = SMILES = Section2 =… …   Wikipedia

  • benzenearsonic acid — benzenarsonrūgštis statusas T sritis chemija formulė C₆H₅AsO₃H₂ atitikmenys: angl. benzenearsonic acid; phenylarsonic acid rus. бензоларсоновая кислота; фениларсоновая кислота ryšiai: sinonimas – fenilarsonrūgštis …   Chemijos terminų aiškinamasis žodynas

  • Organoarsenic chemistry — is the chemistry of compounds containing a chemical bond between arsenic and carbon. A few organoarsenic compounds, also called organoarsenicals, are produced industrially with uses as insecticides, herbicides, and fungicides. In general these… …   Wikipedia

  • benzenarsonrūgštis — statusas T sritis chemija formulė C₆H₅AsO₃H₂ atitikmenys: angl. benzenearsonic acid; phenylarsonic acid rus. бензоларсоновая кислота; фениларсоновая кислота ryšiai: sinonimas – fenilarsonrūgštis …   Chemijos terminų aiškinamasis žodynas

  • бензоларсоновая кислота — benzenarsonrūgštis statusas T sritis chemija formulė C₆H₅AsO₃H₂ atitikmenys: angl. benzenearsonic acid; phenylarsonic acid rus. бензоларсоновая кислота; фениларсоновая кислота ryšiai: sinonimas – fenilarsonrūgštis …   Chemijos terminų aiškinamasis žodynas

  • фениларсоновая кислота — benzenarsonrūgštis statusas T sritis chemija formulė C₆H₅AsO₃H₂ atitikmenys: angl. benzenearsonic acid; phenylarsonic acid rus. бензоларсоновая кислота; фениларсоновая кислота ryšiai: sinonimas – fenilarsonrūgštis …   Chemijos terminų aiškinamasis žodynas

  • Phenylarsonsäure — Strukturformel Allgemeines Name Phenylarsonsäure Andere Namen …   Deutsch Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”