Phthalimide
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Phthalimide
structure -
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CAS No:
85-41-6
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Formula:
C8H5NO2
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Chemical Name:
Phthalimide
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Synonyms:
1H-Isoindole-1,3(2H)-dione;Phthalimide;Isoindole-1,3-dione;1,3-Isoindolinedione;Benzoimide;1,2-Benzenedicarboximide;Phenylimide;Phthalic dicarboximide;Levegal PEW-T;NSC 3108;1,3-Dioxo-1,3-dihydroisoindole;Kladnoite;1,3-Dihydro-2H-isoindole-1,3-dione;2,3-Dihydro-1H-isoindole-1,3-dione
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CAS No:
Description
white to slightly yellowish crystalline flakes
Phthalimide is a white to light tan powder. Slightly acidic. (NTP, 1992)|OtherSolid; WetSolid
Phthalimide is a white to light tan powder. Slightly acidic. (NTP, 1992)|Phthalimide is a dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3.
Phthalimide Basic Attributes
147.13100
147.13
201-603-3
1J6PQ7YI80
3108
DTXSID3026514
MONOCLINIC PRISMS FROM WATER OR BY SUBLIMATION|NEEDLES FROM WATER, PRISMS FROM ACETIC ACID; LEAFLETS (SUBLIMATION)|White crystalline leaflets
2925190090
Characteristics
46.17000
0.89900
Phthalimide is a white to light tan powder. Slightly acidic. (NTP, 1992)
1.367 g/cm3
238 °C
366ºC
165ºC
1.679
Water solubility = 360 mg/l
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 7940 mg/kg
HAS SLIGHTLY ACIDIC PROPERTIES
Ka= 5X10-9
SUBLIMES
Insoluble in water.
Amides and Imides
PHTHALIMIDE is an imide. 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 forms salts with bases. (NTP, 1992)
Safety Information
NONH for all modes of transport
1
R20/21/22
S24/25
TI3920000
Stable under normal shipping and handling conditions.
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.
Literature sources indicate that this compound is combustible. (NTP, 1992)
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures and away from bases. (NTP, 1992)
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)
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
...IT ACTS AS STRONG SKIN, EYE & UPPER RESP TRACT IRRITANT.
Phthalimide was listed as a contaminant found in advanced treatment water in a survey of US cities, including Orange County,CA, on 1/27/76(1).
Toxicity
Phthalimide's production and use in the production of phthalocyanine dyes(1), in the synthesis of primary amines and amino acids in the form of its sodium or potassium salt(1), as synthetic indigo via anthranilic acid(2), as a fungicide(2), in organic synthesis(2) and as a laboratory reagent(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 100(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phthalimide should have high mobility in soil(SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(9). Volatilization of phthalimide should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1X10-8 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 1X10-8 mm Hg(5,SRC). Phthalimide may not be susceptible to direct photolysis on soil surfaces based on its lack of absorption of light at wavelengths >290 nm(6,SRC). According to two activated sludge biodegradation studies, phthalimide will biodegrade rapidly in soil(7,8).|AQUATIC FATE: An estimated Koc value of 100(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that phthalimide should not adsorb to suspended solids and sediment(SRC) in the water(2,SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(8). Phthalimide will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 4.4(2,SRC), from an experimental log Kow(1), suggests that phthalimide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). The half-lives for the base-catalyzed hydrolysis of phthalimide have been determined to be 1.6 days at a pH of 7, and 4 hours at a pH of 8(5,SRC). According to two activated sludge biodegradation studies, phthalimide will biodegrade rapidly in water(6,7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalimide, which has an estimated vapor pressure of 1X10-8 mm Hg at 25 °C(2,SRC) will exist primarily in the particulate phase in the ambient atmosphere. Vapor-phase phthalimide 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 2.6 days(3,SRC). Particulate-phase phthalimide may be physically removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of phthalimide with photochemically produced hydroxyl radicals has been estimated as 6.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). The rate constant for the base-catalyzed hydrolysis of phthalimide has been determined to be 4.8 l/mole-sec(2). This corresponds to a half-life of approximately 1.6 days at a pH of 7, and 4 hours at a pH of 8(2,SRC). Phthalimide may not be susceptible to direct photolysis based on its lack of absorption of light at wavelengths >290 nm(3,SRC).
An estimated BCF value of 4.4 was calculated for phthalimide(SRC), using an experimental log Kow of 1.15(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).
The Koc of phthalimide is estimated as approximately 100(SRC), using an experimental log Kow of 1.15(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that phthalimide should have high mobility in soil(SRC). The adsorptivity of phthalimide is expected to be sensitive to pH since phthalimide has a pKa of 8.3(4).
The Henry's Law constant for phthalimide is estimated as 1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that phthalimide will be essentially nonvolatile from water surfaces(2,SRC). Phthalimide's vapor pressure, 1X10-8 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry and moist soil should not occur(SRC).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 6,820 workers (638 of these are female) are potentially exposed to phthalimide in the USA(1).|Occupational exposure to phthalimide can occur through inhalation of dust, dermal contact, and ingestion(1).
Drug Information
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (NTP, 1992)
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. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital. 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. 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 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)
...IT ACTS AS STRONG SKIN, EYE & UPPER RESP TRACT IRRITANT.|... N-sulfinyl phthalimide fungicides are widely used agricultural products with low acute toxicity. /Phthalimides/
phthalimide
Phthalimide Use and Manufacturing
REACTION OF PHTHALIC ANHYDRIDE WITH AMMONIUM HYDROXIDE OR UREA|FROM PHTHALIC ANHYDRIDE & NH4OH OR (NH4)2CO3.
In production of phthalocyanine dyes.
Curing Retarder
Rubber Tires
25,000 - 100,000 lb|(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
All other basic inorganic chemical manufacturing|1H-Isoindole-1,3(2H)-dione: ACTIVE
Transformation products|Environmental transformation -> Pesticide transformation products (metabolite, successor)
Phthalimide is a known environmental transformation product of folpet.|Phthalimide is a known environmental transformation product of Folpet and Phosmet.
Computed Properties
Molecular Weight:147.13
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:147.032028402
Monoisotopic Mass:147.032028402
Topological Polar Surface Area:46.2
Heavy Atom Count:11
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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