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Phthalamide

Phthalamide structure

Phthalamide 

structure
  • CAS No:

    88-96-0

  • Formula:

    C8H8N2O2

  • Chemical Name:

    Phthalamide

  • Synonyms:

    1,2-Benzenedicarboxamide;Phthalamide;Phthaldiamide;Phthalic acid diamide;o-Carbamoylbenzamide;NSC 5512

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

colourless crystals or white crystalline powder


Phthalamide appears as colorless crystals or off-white powder. (NTP, 1992)


Phthalamide appears as colorless crystals or off-white powder. (NTP, 1992)|Phthalamide is a benzenedicarboxamide. It derives from a phthalic acid.

Phthalamide Basic Attributes

164.164

164.16

201-870-6

7B96053WRS

5512

DTXSID7021158

MINUTE CRYSTALS|Colorless crystals

2924299090

Characteristics

86.2

-1.7

Phthalamide appears as colorless crystals or off-white powder. (NTP, 1992)

1.294g/cm3

228 °C (decomp)

233 °C

214.4ºC

1.612

Water solubility = 200 mg/l

LD50 ipr-rat: 4004 mg/kg APFRAD 48,23,90

Boiling of aqueous or alcoholic solution produces NH3 & phthalimide

Insoluble in water.

Amides and Imides

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).

921.7 CAL/MOL

Safety Information

S22-S24/25

CZ2200000

Stable. Incompatible with acids, strong oxidizing agents.

P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P501

H302

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.

DHEW/NCI; Bioassay of Phthalamide for Possible Carcinogenicity (1979) Technical Rpt Series No. 161 DHEW Pub No. (NIH) 79-1717

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

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)

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)

Toxicity

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.

Phthalamide's production and use as an intermediate in organic synthesis and as a laboratory reagent(1) 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 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).

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).

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).

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).

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).

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. 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)

Phthalamide Use and Manufacturing

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.

Uses

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.

Production

(1977) NOT PRODUCED COMMERCIALLY IN USA|(1979) NOT PRODUCED COMMERCIALLY IN USA

1,2-Benzenedicarboxamide: ACTIVE

Computed Properties

Molecular Weight:164.16
XLogP3:-1.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:164.058577502
Monoisotopic Mass:164.058577502
Topological Polar Surface Area:86.2
Heavy Atom Count:12
Complexity:181
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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