HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzohydroxamic acid
N-HYDROXYBENZAMIDE · BENZHYDROXAMIC ACID · N-BENZOYLHYDROXYLAMINE · BHAM · NSC 3136 · NSC 147248 · benzohydroxamate · n-hydroxy-benzamid
Identifiers & Physical Properties
| CAS No. | 32685-16-8 |
|---|---|
| Molecular formula | C7H7NO2 |
| Average molar mass | 137.14 g/mol |
| Monoisotopic mass | 137.04767847 g/mol |
| SMILES | O=C(NO)c1ccccc1 |
| InChIKey | VDEUYMSGMPQMIK-UHFFFAOYSA-N |
| PubChem CID | 10313 |
| ChEMBL | CHEMBL16300 |
| EC No. | 207-797-6 |
| DTXSID | DTXSID7025421 |
Chemical & Physical Properties
| XLogP | 0.3 |
|---|---|
| Topological polar surface area | 49.3 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 119 |
| LogP (partition coefficient) | 0.26 |
| Solubility | 5 to 10 mg/mL at 74.7 °F (NTP, 1992)Soluble in alcohol. Slightly soluble in ether. Insoluble in benzene.22 g/L (6 ºC) |
| Boiling point | Explodes (NTP, 1992)251.96°C (rough estimate) |
| Melting point | 259 to 266 °F (NTP, 1992)128126-130 °C(lit.) |
| Physical Description | Rhombic crystals or light beige solid. (NTP, 1992) |
| Density | 1.2528 (rough estimate) |
| Refractive index | 1.5030 (estimate) |
| Storage conditions | 2-8°C |
| pKa (acidity coefficient) | pK1: 8.89(0) (20°C) |
| Physical state | Solid |
| Color | Rhombic tablets |
| BRN | 1907585 |
| Stability | Moisture and Temperature Sensitive |
| InChI | 1S/C7H7NO2/c9-7(8-10)6-4-2-1-3-5-6/h1-5,10H,(H,8,9) |
| InChIKey | VDEUYMSGMPQMIK-UHFFFAOYSA-N |
| SMILES | ONC(=O)c1ccccc1 |
| CAS DataBase Reference | 495-18-1(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | K8YW73872D |
| NIST Chemistry Reference | Benzamide, n-hydroxy-(495-18-1) |
| EPA Substance Registry System | Benzohydroxamic acid (495-18-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335-H341 |
| GHS precautionary statements | P201-P261-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xn |
| Risk statements (R) | 68-40-20/21/22 |
| Safety statements (S) | 45-36/37-36-22 |
| Water hazard class (WGK) | 3 |
| RTECS number | DF9650000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29280090 |
| Storage class | 11 - Combustible Solids |
| Toxicity | LD orl-rat: >500 mg/kg NCNSA6 5,26,53 |
| REACH registrations | Inactive |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (97%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H341 (97%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 33 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Benzamide, N-hydroxy-Status: No longer Valid Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24948Benzamide, N-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Health hazards | ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992) |
| Reactive group | Alcohols and PolyolsAmides and Imides |
| Reactivity Profile | N-HYDROXYBENZAMIDE 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). |
| Air and Water Reactions | Slightly soluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (97%)Muta. 2 (97%) |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992) |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | DF9650000 |
| Customs code | 29280090 |
| Toxicity | LD orl-rat: >500 mg/kg NCNSA6 5,26,53 |
| Risk statements (R) | 68-40-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xn |
| Safety statements (S) | 45-36/37-36-22 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335-H341 |
| REACH registrations | Inactive |
| GHS precautionary statements | P201-P261-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
Applications & Uses
Uses
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.
Uses
Benzhydroxamic acid may be employed for the Pd-catalyzed synthesis of benzisoxazolones.
General Description
Rhombic crystals or light beige solid.
Preparation & Synthesis
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).