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HomeProduct name listBenzohydroxamic acid

Benzohydroxamic acid

Synonym(s):N-Hydroxybenzamide

  • CAS NO.:495-18-1
  • Empirical Formula: C7H7NO2
  • Molecular Weight: 137.14
  • MDL number: MFCD00002109
  • EINECS: 207-797-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-25 23:13:37
Benzohydroxamic acid Structural

What is Benzohydroxamic acid?

Chemical properties

Crystalline Solid

The Uses of Benzohydroxamic acid

Benzhydroxamic acid may be employed for the Pd-catalyzed synthesis of benzisoxazolones.

The Uses of Benzohydroxamic acid

Benzhydroxamic 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.

Preparation

To 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 Description

Rhombic crystals or light beige solid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Benzohydroxamic 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 Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Benzohydroxamic acid emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for Benzohydroxamic acid are not available; however, Benzohydroxamic acid is probably combustible.

Safety Profile

Moderately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic fumes of NOx.

Properties of Benzohydroxamic acid

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
pka pK1: 8.89(0) (20°C)
color  Rhombic tablets
Water Solubility  22 g/L (6 ºC)
BRN  1907585
Stability: Moisture and Temperature Sensitive
CAS DataBase Reference 495-18-1(CAS DataBase Reference)
NIST Chemistry Reference Benzamide, n-hydroxy-(495-18-1)
EPA Substance Registry System Benzohydroxamic acid (495-18-1)

Safety information for Benzohydroxamic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H341:Germ cell mutagenicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Benzohydroxamic acid

InChIKey VDEUYMSGMPQMIK-UHFFFAOYSA-N

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