HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Acetoacetanilid
AAA · 3-OXO-N-PHENYLBUTANAMIDE · AAN · ethyl 3-oxo-3-(phenylamino)propanoate · Acetoacetanilid · n-phenylacetoacetamide · Linazol · usafek-1239
Identifikatoren & physikalische Daten
| CAS No. | 102-01-2 |
|---|---|
| Summenformel | C10H11NO2 |
| Durchschnittliche Molmasse | 177,2 g/mol |
| Monoisotopische Masse | 177,07897859 g/mol |
| SMILES | CC(=O)CC(=O)Nc1ccccc1 |
| InChIKey | DYRDKSSFIWVSNM-UHFFFAOYSA-N |
| PubChem CID | 7592 |
| ChEMBL | CHEMBL1604429 |
| EC No. | 202-996-4 |
| DTXSID | DTXSID0024397 |
| Lokaler Name | Acetoacetanilid |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 195 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | Crystal structure |
| Dichte | 1.26 at 68 °F (NTP, 1992) - Denser than waterwill sink1.26 g/ml at 20 °C |
| Color/Form | WHITE CRYSTALLINE SOLIDPLATES OR NEEDLES FROM BENZENE OR PETROLEUM ETHER |
| Löslichkeit | less than 1 mg/mL at 70 °F (NTP, 1992)SLIGHTLY SOL IN WATERSOL IN ALC, CHLOROFORM, ETHER, HOT BENZENE, ACID, HOT PETROLEUM ETHER, ALKALI HYDROXIDE SOLN /KETO FORM/SOL IN ALKALISoluble in oxygenated and chlorinated solvents.Chloroform (Slightly), Methanol (Slightly)5 g/L (20 ºC) |
| Flammpunkt | 325 °F (NTP, 1992)162.7 °C365 °F185 °C (OPEN CUP) |
| Siedepunkt | Decomposes (NTP, 1992)BOILING POINT: DECOMPOSES129°C 24mm |
| Decomposition | SEE ANILINE. ...WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES. /ANILINE/ |
| Schmelzpunkt | 187 °F (NTP, 1992)86 °CGIVES VIOLET COLOR WITH FERRIC CHLORIDEMELTING POINT: 85 °C /KETO FORM/83-88 °C (lit.) |
| Dampfdruck | 0.01 mmHg at 68 °F (NTP, 1992)0.01 [mmHg]5.2X10-5 mm Hg at 25 °C0-0.013Pa at 20-50℃ |
| Physical Description | Acetoacetanilide is a white crystalline solid. (NTP, 1992)CBIDry PowderWhite solid[Hawley] White, odorless crystalline powder[Alfa Aesar MSDS] |
| Stability/Shelf Life | ENOL FORM IS UNSTABLE |
| Dampfdichte | 6.1 (vs air) |
| Brechungsindex | 1.5168 (estimate) |
| Lagerbedingungen | Refrigerator |
| pKa (Säurekonstante) | 12.21±0.46(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White |
| Biologische Quelle | synthetic |
| Merck | 14,58 |
| BRN | 473419 |
| Henry-Konstante | 2.3×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C10H11NO2/c1-8(12)7-10(13)11-9-5-3-2-4-6-9/h2-6H,7H2,1H3,(H,11,13) |
| InChIKey | DYRDKSSFIWVSNM-UHFFFAOYSA-N |
| SMILES | CC(=O)CC(=O)Nc1ccccc1 |
| LogP (Verteilungskoeffizient) | 0.93 at 23℃ |
| CAS Datenbank | 102-01-2(CAS DataBase Reference) |
| NIST chemische Informationen | Butanamide, 3-oxo-N-phenyl-(102-01-2) |
| EPA chemische Informationen | Acetoacetanilide (102-01-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 2.5% (12 of 477) of reports.WarningH302 (97.3%): Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 477 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Butanamide, 3-oxo-N-phenyl-Butanamide, 3-oxo-N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanamide, 3-oxo-N-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 27-06-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/14590Acetoacetanilide: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Brandpotenzial | FIRE HAZARD: SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. |
| Gesundheitsgefahren | ACUTE/CHRONIC HAZARDS: This compound is a weak allergen. When heated to decomposition it emits toxic fumes. (NTP, 1992) |
| Gefahrenübersicht | Reports of reversible eye burns in humansNot irritating to skin and mildly irritating to eyes of rabbitsNo evidence of skin sensitization in guinea pigsCauses slight methemoglobinemia and significant formation of Heinz bodies in cats following single oral administration of 100 mg/kgHemolytic anemia and corresponding injury to liver, spleen, and kidneys observed in 28-day oral study of rats (850 mg/kg/day and, to some extent, at 100 mg/kg/day)Emergency treatment: PhenacetinPhenacetin was used as a pain-relieving drug, but has not been available in the US since 1983. Can cause methemoglobinemia after ingestion >1 gram/dayCan cause renal papillary necrosis following ingestion of large doses for years[HSDB] A weak allergen[CAMEO] A mild skin irritantCan be absorbed through skin[Alfa Aesar MSDS] |
| Reaktive Gruppe | Amides and Imides |
| TSCA-Anforderungen | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble in 51 FR 41329.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Acetoacetanilide is included on this list. |
| Reactivity Profile | Organic amides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides with strong reducing agents. Amides are very weak bases (weaker than water). 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). Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. |
| Air and Water Reactions | Water insoluble. |
| NFPA Hazard Classification | 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Acute Tox. 4 (97.3%) |
| Hazardous Reactivities and Incompatibilities | SEE ANILINE. ...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS. /ANILINE/ |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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. |
| Brandbekämpfungsverfahren | ALCOHOL FOAM, WATER MIST, CARBON DIOXIDE, DRY CHEMICAL."ALCOHOL" FOAM. WATER OR FOAM MAY CAUSE FROTHING. |
| 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) |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that acetoacetanilide will have high mobility in soil(SRC). Volatilization of acetoacetanilide from moist soil surfaces is not expected to occur(SRC) given an estimated Henry's Law constant of 4.2X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of acetoacetanilide from dry soil surfaces may not exist(SRC) based on an extrapolated vapor pressure of 5.2X10-5 mm Hg(4,SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that acetoacetanilide is not expected to adsorb to suspended solids and sediment in water(SRC). Acetoacetanilide is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 4.2X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(5), an estimated BCF value of 3.4(1,SRC), from an estimated log Kow(4,SRC), suggests that bioconcentration in aquatic organisms is low(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetoacetanilide, which has an extrapolated vapor pressure of 5.2X10-5 mm Hg at 25 °C(2,SRC), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acetoacetanilide 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 1.2 days(3,SRC). Particulate-phase acetoacetanilide may be physically removed from the air by wet and dry deposition(SRC). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for acetoacetanilide can be estimated to be about 12(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that acetoacetanilide has very high mobility in soil(SRC). |
| TSCA Test Submissions | Acetoacetanilide (CAS# 102-01-2) was evaluated for acute oral toxicity. The test substance was administered by oral gavage to 10 rats (strain not specified) at a dose-range of 200-3200 mg/kg b.w. Clinical signs at dose levels greater than 800 mg/kg included slight to moderate weakness, vasodilation, tremors and a possible methemoglobin response. At 3200 mg/kg, clinical signs included prostration and rapid heart rates. The LD50 was determined to be 1600 mg/kg for males, and 1130 mg/kg for females. The test substance was determined to be slightly toxic.Acetoacetanilide (CAS# 102-01-2) was evaluated for acute oral toxicity. The test substance was administered by oral gavage to 10 mice (strain and sex not specified) at a dose-range of 200-3200 mg/kg of body weight. Clinical signs included a dose-related increase in weakness, dark eyes, vasodilation, rough coat, prostration, gasping, and yellow-brown urine. The LD50 was determined to be in a range between 800-1600 mg/kg.Acetoacetanilide (CAS# 102-01-2) was evaluated for acute intraperitoneal toxicity. The test substance was administered by intraperitoneal injection to 10 mice (strain and sex not specified) at a dose-range of 200-3200 mg/kg of body weight. Clinical signs included a dose-related increase in weakness, dark eyes, vasodilation, rough coat, prostration, gasping, and yellow-brown urine. The LD50 was determined to be in a range between 800-1600 mg/kg.Acetoacetanilide (CAS# 102-01-2) was evaluated for acute dermal toxicity. The test substance was applied to the cuff of 4 guinea pigs (strain and sex not specified) at a dose-range of 0.25-1.0 g/kg of body weight. Clinical signs included slight edema and erythema and a small blister-like spot. Desquamation and sparse hair was noted at one week, with desquamation persisting to the 2nd week. The LD50 was determined to be in a range between 0.5 and 1.0 g/kg b.w.For more TSCA Test Submissions (Complete) data for ACETOACETANILIDE (8 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | IT IS WELL KNOWN TO PRODUCE CYANOSIS IN SOME HUMANS WHEN TAKEN REPEATEDLY, POSSIBLY DUE TO FORMATION OF SULFHEMOGLOBIN. LARGE DOSES IN ACUTE POISONING PRODUCE METHEMOGLOBIN... /ACETANILIDE/.../"COAL TAR ANALGETICS" INCL ACETANILIDE/ ARE DEPRESSANTS OF CNS. SYMPTOMS OF NAUSEA & VOMITING, VERTIGO & RINGING IN EARS...OCCUR WITH LARGE DOSES OR IN... SENSITIVE INDIVIDUALS WITH THERAPEUTIC DOSES. SWEATING MAY BE PROFUSE. LARGE DOSES LEAD TO MENTAL CONFUSION, MUSCULAR INCOORDINATION & COMA. /ACETANILIDE/CIRCULATORY COLLAPSE, WITH COLD EXTREMITIES, PALENESS...FEEBLE RAPID PULSE & DYSPNEA, & COMA, WITH FIXED, SEMI-DILATED PUPILS, IS CHARACTERISTIC FINDING IN ACUTE ACETANILIDE POISONING. /ACETANILIDE/IT MAY...CAUSE CONTACT DERMATITIS & INHALATION OR INGESTION MAY CAUSE AN ECZEMATOUS ERUPTION OF THE SKIN. /ACETANILIDE/For more Human Toxicity Excerpts (Complete) data for ACETOACETANILIDE (9 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Acetoacetanilide's production and use as a chemical intermediate in organic syntheses and rubber compounding(1), and in the production of dyes and fungicides(2,3) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | Biodegradation studies of acetoacetanilide based on COD measurements, using an activated sludge seed indicate that acetoacetanilide is biodegradable(1,2). One study used an initial concentration of acetoacetanilide of 248 ppm and reported an 18 percent COD removal over a period of 24 hours(1). A second study used an initial concentration of 100 ppm acetoacetanilide and reported an 87 percent COD removal over a 24 hour period(2). |
| Environmental Bioconcentration | An estimated BCF value of 3.4 was calculated for acetoacetanilide(SRC), using an estimated log Kow of 1.0(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for acetoacetanilide is estimated as 4.2X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that acetoacetanilide will be essentially nonvolatile from water surfaces(2,SRC). Acetoacetanilide's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). The potential for volatilization of acetoacetanilide from dry soil surfaces may not exist(SRC) based on the extrapolated vapor pressure of 5.2X10-5 mm Hg(3,SRC). |
| Non-Human Toxicity Excerpts | ... The admin of a single oral dose of 100 mg/kg/body wt to cats resulted in a slight methemoglobin development and marked formation of Heinz bodies. Following oral admin of 850 mg/kg/body wt/day and, to a lesser extent, 100 mg/kg/body wt/day to rats for 28 days, acetoacetanilide has lead primarily to hemolytic anemia with associated damage to the liver, spleen and kidneys.... In rabbits, acetoacetanilide is not irritating to the skin and slightly irritating to the eyes. There is no indications of skin sensitizing potential in guinea pigs. ...... Acetoacetanilide is not mutagenic in the Salmonella/microsome test or in the spot test in Escherichia coli. ...... Fertility and offspring viability were impaired in mice in a combined subchronic feeding and fertility study (10,000, 5,000 and 1,000 ppm in the dietca 1230, 650 and 130 mg/kg body wt). ... |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of acetoacetanilide with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1.2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Acetoacetanilide is not expected to undergo hydrolysis in the environment due to the lack of functional groups to hydrolyze. Acetoacetanilide may undergo direct photolysis based on its weak absorption of UV light between 290-320 nm in methanol(2). |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 1100 workers are potentially exposed to acetoacetanilide in the US(1). Occupational exposure to acetoacetanilide may occur through dermal contact with this compound at workplaces where it is produced or used(SRC). |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2921419000 |
| RTECS-Nr. | AK4200000 |
| R-Sätze (R) | 21/22 |
| Toxizität | LD50 orl-rat: 5400 mg/kg LONZA# 08FEB79 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 102-01-2(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 843 °F |
Anwendungen & Verwendung
Beschreibung
Das Acetessigsäureanilid bildet ein weißes, in Wasser unlösliches Pulver. Die Substanz kuppelt an der reaktiven Methylengruppe mit Diazoniumsalzen zu, meist unlöslichen, Azofarbstoffen und wird daher in der chemischen Industrie zur Herstellung von Pigment
Beschreibung
Acetessigsäureanilid bildet ein weißes, in Wasser unlösliches Pulver. Die Substanz kuppelt an der reaktiven Methylengruppe mit Diazoniumsalzen zu, meist unlöslichen, Azofarbstoffen und wird daher in der chemischen Industrie zur Herstellung von Pigmenten (z.B. Hansagelb G) für die Lackindustrie verwendet.
Verwenden
Acetoacetanilide is used as intermediate for the manufacture of organic pigments and dyestuffs.