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2-Hydroxybenzamid
2-HYDROXYBENZAMIDE · Cetamide · Salamide · Salicylamid · O-HYDROXYBENZAMIDE · Algamon · Benesal · OHB
Identifikatoren & physikalische Daten
| CAS No. | 65-45-2 |
|---|---|
| Summenformel | C7H7NO2 |
| Durchschnittliche Molmasse | 137,14 g/mol |
| Monoisotopische Masse | 137,04767846 g/mol |
| SMILES | NC(=O)c1ccccc1O |
| InChIKey | SKZKKFZAGNVIMN-UHFFFAOYSA-N |
| PubChem CID | 5147 |
| ChEMBL | CHEMBL27577 |
| ChEBI | CHEBI:32114 |
| EC No. | 200-609-3 |
| DTXSID | DTXSID3021726 |
| Lokaler Name | 2-Hydroxybenzamid |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,3 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 136 |
| Arzneimittel | DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15 |
| Kosmetika | Keratolytic |
| pH | ABOUT 5 @ 28 °C (AQ SOLN) |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | Log Kow = 1.281.280 |
| Geschmack | SOMEWHAT BITTER |
| Dichte | 1.175 at 284 °F (NTP, 1992) - Denser than waterwill sink1.175 @ 140 °C/4 °C1,175 g/cm3 |
| Color/Form | WHITE OR SLIGHTLY PINK CRYSTALLINE POWDERYELLOW LEAFLETS FROM DILUTE ALCOHOL |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)SOLUBILITY IN WATER: 0.2% @ 30 °C0.8% @ 47 °CIN GLYCEROL: 2.0% @ 5 °C5.0% @ 39 °C10.0% @ 60 °CIN PROPYLENE GLYCOL: 10.0% @ 5 °CSLIGHTLY SOL IN NAPHTHA, CARBON TETRACHLORIDEFREELY SOL IN SOLN OF ALKALIESSOL IN CHLOROFORM, ALC, ETHERmethanol: 0.1 g/mL, clear<0.1 g/100 mL at 20 ºC |
| Human Drugs | Pharmaceuticals |
| Siedepunkt | 518 °F at 760 mmHg (decomposes) (NTP, 1992)181.5 °C @ 14 MM HG181.50 °C. @ 760.00 mm Hg270°C |
| Decomposition | DANGEROUSWHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES OF /NITROGEN OXIDES/.270°C |
| Schmelzpunkt | 140-144 °C(lit.) |
| Brechungsindex | 1.5323 (estimate) |
| Flammpunkt | 181°C/14mm |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | pKa 8.13(H2O t = 37) (Uncertain) |
| Farbe | White |
| Geruch | Odorless |
| Merck | 14,8328 |
| BRN | 742439 |
| Henry-Konstante | 2.0×104 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| Stabilität | Stable. Light sensitive. Incompatible with strong bases, strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | KERATOLYTIC |
| InChI | 1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10) |
| InChIKey | SKZKKFZAGNVIMN-UHFFFAOYSA-N |
| SMILES | NC(=O)c1ccccc1O |
| LogP (Verteilungskoeffizient) | 1.280 |
| CAS Datenbank | 65-45-2(CAS DataBase Reference) |
| NIST chemische Informationen | Benzamide, 2-hydroxy-(65-45-2) |
| EPA chemische Informationen | o-Hydroxybenzamide (65-45-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (99.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 851 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: Benzamide, 2-hydroxy-Status: Active Update: 21-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2210Salicylamide: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound include dizziness, drowsiness, nausea, vomiting, epigastric distress, allergic reactions and blood dyscrasias. It can cause central nervous depression, hypotension and respiratory arrest. This compound may greatly potentiate the hepatic toxicity of acetaminophen. It may also cause hyperpnea, renal failure, prolonged bleeding time, a mild burning pain in the mouth, throat and abdomen, lethargy, tinnitus hearing loss, excitability, delirium, fever, sweating, dehydration, incoordination, restlessness, ecchymoses, coma, convulsions, cyanosis, oliguria, uremia, pulmonary edema, gastric ulcer, weight loss and mental deterioration. Other symptoms may include skin eruptions, headache, difficulty in hearing, dimness of vision, lassitude and hyperventilation. |
| Reaktive Gruppe | Amides and Imides |
| Reactivity Profile | 2-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). This chemical may be sensitive to prolonged exposure to light. (NTP, 1992) |
| Air and Water Reactions | It darkens on exposure to air. (NTP, 1992). Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (99.3%)Acute toxicity (Oral) - Category 4 |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992) |
| Erste Hilfe | 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. |
| Lagerbedingungen | Salicylamide preparations generally should be stored in well-closed containers at a temperature less than 40 °C, preferably between 15 and 30 °C. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing 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. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 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) |
| Wechselwirkungen | ...MUTUAL COMPETITIVE INHIBITION IN THE FORMATION OF SULFATES, AND PROBABLY GLUCURONIDES, OF ACETAMINOPHEN AND SALICYLAMIDE IN MAN /HAS BEEN DEMONSTRATED/.BIOLOGICAL HALF-LIFE OF SALICYLAMIDE...INCR SOMEWHAT BY IV ASCORBIC ACID & MORE BY ORAL ASCORBIC ACIDPLASMA LEVELS OF SALICYLAMIDE & GLUCURONIDE METABOLITE INCR WHILE LEVELS OF SULFATE METABOLITE DECR. ...MAX INHIBITION OF SULFATE CONJUGATION OR SALICYLAMIDE BY ASCORBIC ACID WHEN BOTH...IN HIGH CONCN IN INTESTINAL WALL & LIVER.SALICYLAMIDE ADMIN DECR RADIOSULFATE UPTAKE BY MATERNAL SERUM & LIVER, FETUS, & PLACENTAEFFECTS BEING DOSE-DEPENDENT.IN THE PRESENCE OF SALICYLAMIDE, 7,12-DIMETHYLBENZ(A)ANTHRACENE LOST ITS ABILITY TO INDUCE DNA-REPAIR SYNTHESIS IN RAT HEPATOCYTES. THIS FAILURE TO INDUCE DNA REPAIR IS DUE TO INHIBITION OF A SULFATE ESTER INTERMEDIATE.For more Interactions (Complete) data for SALICYLAMIDE (12 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 118(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that salicylamide will have high mobility in soil(SRC). Volatilization of salicylamide will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 6.9X10-6 mm Hg(5,SRC). Insufficient data are available to determine the rate or importance of biodegradation of salicylamide in soil(SRC), but its structure would suggest rapid biodegradation(6,SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 118(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that salicylamide may not adsorb to suspended solids and sediment(SRC) in the water. Salicylamide will be essentially nonvolatile from water surfaces based on an estimated Henry's Law constant of 2.9X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated BCF value of 5.5(3,SRC), from an experimental log Kow(2), suggests that salicylamide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5). Insufficient data are available to determine the rate or importance of biodegradation of salicylamide in water(SRC), but its structure would suggest rapid biodegradation(6,SRC).ATMOSPHERIC FATE: According to a suggested classification scheme(1), an estimated vapor pressure of 6.9X10-6 mm Hg at 25 °C(2,SRC) indicates that salicylamide will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase salicylamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be about 12 hours(3,SRC). Particulate-phase salicylamide may be physically removed from the air by wet and dry deposition(SRC). The reaction of phenols with nitrate radicals may also be important(4). |
| Soil Adsorption/Mobility | The Koc of salicylamide is estimated as approximately 118(SRC), using an experimental log Kow of 1.28(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that salicylamide has high mobility in soil(SRC). |
| Human Toxicity Excerpts | GASTROINTESTINAL IRRITATION OCCURS IN ABOUT 10% OF PATIENTS, AND DROWSINESS AND DIZZINESS ARE OBSERVED IN APPROXIMATELY 10 AND 20%, RESPECTIVELY.In contrast to salicylates, salicylamide overdosage produces CNS depression, hypotension, and eventually respiratory arrest, but does not produce excitement, seizures, metabolic acidosis, or hypoprothrombinemia.Little information is available on the acute toxicity of salicylamide. Salicylamide is generally considered to be less toxic than salicylates in overdosage but unequivocal evidence in humans is lacking ... .Toxic epidermal necrolysis (Lyell's syndrome) with erythematous skin lesions and bulla formation developed in a 4 yr old girl. An accurate diagnosis using the cryostat technique on top of a bulla was available within 1 hr of hospital admission. The course was unusually mild, probably because of early treatment with corticosteroids. Skin prick tests revealed salicylamide was the agent responsible for inducing the /condition/. The patient was advised to avoid this substance for the rest of her life. |
| Artificial Pollution Sources | Salicylamide's production and use as an analgesic(1), antipyretic(1), antirheumatic(2), sedative(2), and for protection against mildew and fungus in a variety of soaps, salves, lotions, and oils(3) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF value of 5.5 was calculated for salicylamide(SRC), using an experimental log Kow of 1.28(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for salicylamide is estimated as 2.9X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that salicylamide will be essentially nonvolatile from water surfaces(2,SRC). Salicylamide's low vapor pressure, 6.9X10-6 mm Hg(3,SRC) and low Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil will not occur(SRC). |
| Non-Human Toxicity Excerpts | EXPERIMENTS IN RATS SHOW...A MUCH MORE RAPID AND GREATER CENTRAL NERVOUS SYSTEM DEPRESSANT EFFECT THAN ASPIRIN... THIS DRUG IS REPORTED TO BE LESS IRRITATING TO THE GASTRIC MUCOSA OF THE RAT THAN IS ASPIRIN..../IT/ IS TEN TIMES AS TOXIC TO THE CAT AS IT IS TO THE RAT, RABBIT, DOG...CAUSING ACUTE OLIGURIC NEPHROSIS..../SALICYLAMIDE/ PRODUCES /SRP: CNS DEPRESSION/, DEPRESSION, PARALYSIS, & DEATH IN HIGH DOSAGE WHEREAS COMPARABLE USE OF ORDINARY SALICYLATES PRODUCES STIMULATIONS & CONVULSIONS...FOLLOWED BY DEATH.ABSENCE OF A GLUCURONIDATION PATHWAY IN CAT COULD EXPLAIN THE VERY MUCH GREATER TOXICITY OF SALICYLAMIDE IN THIS SPECIES COMPARED WITH MAN & MOST ANIMALS.For more Non-Human Toxicity Excerpts (Complete) data for SALICYLAMIDE (7 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of salicylamide with photochemically produced hydroxyl radicals has been estimated as 3.25X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The reaction of phenols with nitrate radicals may also be important(2). |
| Probable Routes of Human Exposure | Based on its use as an analgesic(1), antipyretic(1), antirheumatic(2), sedative(2), and for protection against mildew and fungus in a variety of soaps, salves, lotions, and oils(3), the general population may be exposed to salicylamide through ingestion of salicylamide containing pharmaceuticals and through dermal contact from the use of certain soaps and lotions(SRC). |
| Environmental Fate/Exposure Summary | Salicylamide's production and use as an analgesic, antipyretic, antirheumatic, sedative, and for protection against mildew and fungus in a variety of soaps, salves, lotions, and oils may result in its release to the environment through various waste streams. If released to soil, salicylamide will have high mobility. Volatilization of salicylamide will not be important from moist or dry soil surfaces. Insufficient data are available to determine the rate or importance of biodegradation of salicylamide in soil or water but its structure would suggest rapid biodegradation. If released to water, salicylamide may not adsorb to suspended solids and sediment. Salicylamide will be essentially nonvolatile from water surfaces. An estimated BCF value of 5.5(3,SRC) suggests that salicylamide will not bioconcentrate in aquatic organisms. If released to the atmosphere, salicylamide will exist in both the vapor and particulate phases. Although salicylamide has not been detected in the atmosphere, vapor-phase salicylamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 12 hours. Particulate-phase salicylamide may be physically removed from the air by wet and dry deposition. The reaction of phenols with nitrate radicals may also be important. The general population may be exposed to salicylamide through ingestion of salicylamide containing pharmaceuticals and use of certain soaps and lotions. (SRC) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3249 |
| Zollcode | 29214300 |
| RTECS-Nr. | VN6475000 |
| R-Sätze (R) | 22-36/37/38-20/21/22 |
| Toxizität | LD50 orally in mice: 1.4 g/kg (Hart) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 65-45-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Salicylamide is less acidic (pKa 8.2) than other salicylic acid derivatives. Although poorly soluble in water, stable solutions can be formed at pH 9 through ionization of the phenolic group. It is absorbed from the GI tract on oral administration and is rapidly metabolized to inactive metabolites by intestinal mucosa, but not by hydrolysis. Activity appears to reside in the intact molecule. It is approximately 40 to 55% plasma protein bound, and it competes with other salicylates and acetaminophen for glucuronide conjugation, decreasing the extent of conjugation of these other drugs.
Verwenden
salicylamide is an analgesic, fungicide, and anti-inflammatory ingredient used to soothe the skin. It is an aromatic amide.