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Benzohydroxamic acid

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CAS:495-18-1
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Benzohydroxamic acid Basic information
Product Name:Benzohydroxamic acid
Synonyms:BENZHYDROXAMIC ACID;BENZOHYDROXAMIC ACID;N-HYDROXYBENZAMIDE;N-BENZOYLHYDROXYLAMINE;Benzamide,N-hydroxy-;benzohydroxamate;n-hydroxy-benzamid;Phenylhydroxamic acid
CAS:495-18-1
MF:C7H7NO2
MW:137.14
EINECS:207-797-6
Product Categories:Aromatics;AMIDE;Hydroxylamines;Hydroxylamines (N-Substituted);Inhibitors
Mol File:495-18-1.mol
Benzohydroxamic acid Structure
Benzohydroxamic acid Chemical Properties
Melting point 126-130 °C(lit.)
Boiling point 251.96°C (rough estimate)
density 1.2528 (rough estimate)
refractive index 1.5030 (estimate)
storage temp. 2-8°C
solubility Soluble in alcohol. Slightly soluble in ether. Insoluble in benzene.
form Solid
pkapK1: 8.89(0) (20°C)
color Rhombic tablets
Water Solubility 22 g/L (6 ºC)
BRN 1907585
Stability:Moisture and Temperature Sensitive
InChIKeyVDEUYMSGMPQMIK-UHFFFAOYSA-N
CAS DataBase Reference495-18-1(CAS DataBase Reference)
NIST Chemistry ReferenceBenzamide, n-hydroxy-(495-18-1)
EPA Substance Registry SystemBenzohydroxamic acid (495-18-1)
Safety Information
Hazard Codes Xn
Risk Statements 68-40-20/21/22
Safety Statements 45-36/37-36-22
WGK Germany 3
RTECS DF9650000
TSCA Yes
HS Code 29280090
ToxicityLD orl-rat: >500 mg/kg NCNSA6 5,26,53
MSDS Information
ProviderLanguage
N-Hydroxybenzamide English
SigmaAldrich English
ACROS English
ALFA English
Benzohydroxamic acid Usage And Synthesis
Chemical PropertiesCrystalline Solid
UsesBenzhydroxamic acid may be employed for the Pd-catalyzed synthesis of benzisoxazolones.
UsesBenzhydroxamic acid is used as precursor in the synthesis of novel mono-anionic and di-anionic hydroxamato complexes by reacting with BiPh3 and Bi(O(t)Bu)3, which has anti-bacterial activity against helicobacter pylori. It is used in the photometric determination of trace amounts of vanadium in alloy steels by making mixed-ligand vanadium chelates with ammonium thiocyanate. It is also involved in the palladium catalyzed synthesis of benzisoxazolones.
PreparationTo a rapidly stirred suspension of 19.6 gm (0.35 mole) of powdered anhydrous potassium hydroxide in 120 ml of pyridine, maintained at 0-5°C, is a added a solution of 13.9 gm (0.2 mole) of hydroxylamine hy­drochloride in 100 ml of pyridine.
While maintaining the reaction temperature at 0-5°C, 15 gm (0.1 mole) of ethyl benzoate is added. Vigorous stirring is continued at room tempera­ture for 6 hr. Then the solids are filtered off. The solids are washed with cold water to remove inorganic coproducts. The remainder, recrystallized from aqueous ethanol, represents a 94% yield of potassium benzohy­droxamate.
This salt is triturated with cold 0.01 TV hydrochloric acid. From this mixture, by the usual procedures, 12.5 gm (91% overall) of benzohydrox­amic acid is isolated, m.p. 131°C (from aqueous alcohol).
Preparation of Benzohydroxamic Acid
Synthesis Reference(s)Tetrahedron Letters, 33, p. 5055, 1992 DOI: 10.1016/S0040-4039(00)61187-5
General DescriptionRhombic crystals or light beige solid.
Air & Water ReactionsSlightly soluble in water.
Reactivity ProfileBenzohydroxamic acid is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition Benzohydroxamic acid emits toxic fumes of nitrogen oxides.
Fire HazardFlash point data for Benzohydroxamic acid are not available; however, Benzohydroxamic acid is probably combustible.
Safety ProfileModerately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic fumes of NOx.
Tag:Benzohydroxamic acid(495-18-1) Related Product Information
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