Grundinformationen
- Standard-SMILES
NC(=O)c1ccccc1C(N)=O- InChIKey
NAYYNDKKHOIIOD-UHFFFAOYSA-N- Summenformel
- C8H8N2O2
- Durchschnittliche Molmasse
- 164,16 g/mol
- Monoisotopische Masse
- 164,0585775
Namen und Bezeichner
- Bevorzugter Name
- Phthalamide
- IUPAC
- benzene-1,2-dicarboxamide
- Lokaler Name
- Phthalamid
- Englischer Name
- PHTHALAMIDE
- Summenformel
- C8H8N2O2
- Molmasse
- 164.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
88-96-0- PubChem CID
- 6956
- DTXSID
DTXSID7021158- ChEMBL
CHEMBL3189112- ChEBI
CHEBI:38799- UNII
- 7B96053WRS
- EC Number
- 201-870-6
- Nikkaji
- J29.505A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -1,7
- Polarare Oberfläche (TPSA)
- 86,2 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 181
Experimentelle und physikochemische Eigenschaften
Color/Form
MINUTE CRYSTALS
Colorless crystals
Solubility
less than 1 mg/mL at 66 °F (NTP, 1992)
SLIGHTLY SOL IN COLD WATER, METHANOL; MORE SOL IN HOT SOLVENTS
SLIGHTLY SOL IN ETHER
Water solubility = 200 mg/l
Melting Point
442 °F (decomposes) (NTP, 1992)
228 °C, DECOMPOSES AT MELTING POINT
MP: 221-223 °C /COMMERCIAL GRADES/
Physical Description
Phthalamide appears as colorless crystals or off-white powder. (NTP, 1992)
Colorless solid; [Hawley]
Physikochemische Eigenschaften
- Schmelzpunkt
- 223 °C · 223°C (dec.)
- Siedepunkt
- 291.62 °C · 291.62°C (rough estimate)
- Dichte
- 1.2739 · 1.2739 (rough estimate)
- Brechungsindex
- 1.6 · 1.6000 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- Aggregatzustand
- powder to crystal
- pka
- 1 · pK1:3.79(0) (25°C)
- Farbe
- White to Almost white
- Wasserlöslichkeit
- 0.2 g/L · 0.2g/L(20 ºC)
- Merck
- 14 · 14,7369
- BRN
- 1868220 · 1868220
- Henry's Law Constant
- 7 · 7.0×106 mol/(m3Pa) at 25℃, HSDB (2015)
- Stabilität
- Stable. Incompatible with acids, strong oxidizing agents.
- CAS Datenbank
- 88 · 88-96-0(CAS DataBase Reference)
- EPA chemische Informationen
- Phthalamide (88-96-0)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 2 reports by companies from 2 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.
Gefahrenhinweise
Reactivity Profile
PHTHALAMIDE 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 is incompatible with acids. (NTP, 1992).
Sicherheit und Schutzausrüstung
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 area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if 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 under ambient temperatures. (NTP, 1992)
Disposal Methods
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 a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2.7(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phthalamide should have very high mobility in soil(SRC). Volatilization of phthalamide may not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.4X10-12 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 3.25X10-8 mm Hg(5,SRC). Insufficient data are available to determine the rate or importance of biodegradation of phthalamide in soil(SRC).
AQUATIC FATE: An estimated Koc value of 2.7(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that phthalamide would not adsorb to suspended solids and sediment(SRC) in water(2,SRC). Phthalamide would be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1.4X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 0.03(3,SRC), from an experimental log Kow(1), suggests that phthalamide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). Insufficient data are available to determine the rate or importance of biodegradation of phthalamide in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalamide, which has an estimated vapor pressure of 3.25X10-8 mm Hg at 25 °C(2,SRC) will exist peimarily in the particulate phase in the ambient atmosphere. Vapor-phase phthalamide 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 3.4 days(3,SRC). Particulate-phase phthalamide may be physically removed from the air by wet and dry deposition(SRC).
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=88-96-0]
Soil Adsorption/Mobility
The Koc of phthalamide is estimated as approximately 2.7(SRC), using an experimental log Kow of -1.73(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that phthalamide should have very high mobility in soil(SRC).
Carcinogen Classification
Phthalamide
TR-161: Bioassay of Phthalamide for Possible Carcinogenicity (CASRN 88-96-0) (1979 )
12/13/78
No Evidence
No Evidence
No Evidence
Environmental Bioconcentration
An estimated BCF value of 0.03 was calculated for phthalamide(SRC), using an experimental log Kow of -1.73(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 phthalamide is estimated as 1.4X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that phthalamide will be essentially nonvolatile from water surfaces(2,SRC). Phthalamide's vapor pressure, 3.25X10-8 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil should not occur(SRC).
Non-Human Toxicity Excerpts
PHTHALAMIDE HAD LOW BUT SIGNIFICANT INCIDENCE OF SPECIFIC MALFORMATIONS WITH RESPECT TO CONTROLS AFTER BEING INJECTED INTO FRESH FERTILE WHITE LEGHORN EGGS.
... It is concluded that under the conditions of this bioassay, phthalamide was not carcinogenic for F344 rats or B6C3F1 mice of either sex. ... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of phthalamide with photochemically produced hydroxyl radicals has been estimated as 4.75X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 3.4 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
Environmental Fate/Exposure Summary
Phthalamide's production and use as an intermediate in organic synthesis and as a laboratory reagent may result in its release to the environment through various waste streams. If released to soil, phthalamide should have very high mobility. Volatilization of phthalamide may not be important from moist or dry soil surfaces. Insufficient data are available to determine the rate or importance of biodegradation of phthalamide in soil or water. If released to water, phthalamide would not adsorb to suspended solids and sediment. Phthalamide would be essentially non-volatile from water surfaces. An estimated BCF value of 0.03 suggests that phthalamide will not bioconcentrate in aquatic organisms. If released to the atmosphere, phthalamide will exist primarily in the particulate phase. Vapor-phase phthalamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 3.4 days. Particulate-phase phthalamide may be physically removed from the air by wet and dry deposition. (SRC)
National Toxicology Program Studies
A bioassay of phthalamide for possible carcinogenicity was conducted by administering the test chemical in feed to F344 rats and B6C3Fl mice. Groups of 50 rats of each sex were admin phthalamide at one of two doses, either 15,000 or 30,000 ppm for the males and either 5,000 or 10,000 ppm for the females, for 106 wk. Groups of 50 mice of each sex were admin the test chemical at one of two doses, 25,000 or 50,000 ppm for the males, and at one of three doses, 6,200, 12,500, or 25,000 ppm, for the females, for 103 or 105 wk. Matched controls consisted of 20 untreated rats of each sex, 20 untreated male mice, and two groups of 20 untreated female mice. All surviving rats and mice were /sacrificed/ at the end of admin of the test chemical. ... It is concluded that under the conditions of this bioassay, phthalamide was not carcinogenic for F344 rats or B6C3F1 mice of either sex. ... Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.
Regulatorische Informationen
Sicherheitsdaten
- tsca
- TSCA listed
- hs_code
- 29242990
- RTECS-Nr.
- CZ2200000
- Toxizität
- LD50 ipr-rat: 4004 mg/kg APFRAD 48,23,90
- safety_code
- 22-24/25
- Giftige Stoffe Daten
- 88-96-0(Hazardous Substances Data)
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as intermediate and laboratory reagent; [Hawley] Used as a curing agent for epoxy resins, e.g., paints; [NTP]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
LABORATORY REAGENT; CHEMICAL INTERMEDIATE FOR CI PIGMENT BLUE 15, O-PHTHALONITRILE
Intermediate in organic synthesis, laboratory reagent.
By stirring phthalimide with cold concentrated ammonia solution; by the reaction of phthalyl chloride and ammonia.
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN USA
(1979) NOT PRODUCED COMMERCIALLY IN USA
Methods of Manufacturing
By stirring phthalimide with cold, concentrated ammonia solution; by the reaction of phthalyl chloride and ammonia.
PREPD FROM PHTHALIC ANHYDRIDE & ANHYDROUS AMMONIA IN BENZENE.
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