Phthalonitrile
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Phthalonitrile
structure -
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CAS No:
91-15-6
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Formula:
C8H4N2
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Chemical Name:
Phthalonitrile
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Synonyms:
1,2-Benzenedicarbonitrile;Phthalonitrile;o-Dicyanobenzene;Phthalodinitrile;o-Benzenedinitrile;1,2-Dicyanobenzene;o-Cyanobenzonitrile;o-Benzenedicarbonitrile;1,2-Benzodinitrile;1,2-Bis(cyano)benzene;NSC 17562;o-Benzodinitrile
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CAS No:
Description
Phthalonitrile is a crystalline powder having a faint grayish yellow color and a slighty aromatic odor, similar to benzonitrile. Phthalonitrile was first described in 1896 when it was isolated during the diazotization of 2-aminobenzonitrile. The compound is sparingly soluble in water (ca. 1 g/L) and soluble in acetone, nitrobenzene, and benzonitrile. It cannot be distilled and polymerizes if heated above the melting point. It is not explosive and is difficult to ignite, but the dust can explode
Liquid; OtherSolid|YELLOW CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.
Phthalonitrile Basic Attributes
128.13
128.13
775028
202-044-8
978627YAJU
0670
17562
3276
DTXSID8029604
NEEDLES FROM WATER OR PETROLEUM ETHER|Buff-colored crystals|Faint grayish yellow
29269095
Characteristics
47.6
1
White to beige Crystals or Crystalline Powder
1.238 g/cm3
138 °C
294 °C
162°C
1.566
H2O: 0.56 g/L (25 ºC);benzene: 50 mg/mL, clear
Store below +30°C.
Vapour pressure, Pa at 20°C: 4
LD50 orally in Rabbit: 85 mg/kg
Slightly aromatic
Specific heat = 1.30 J/g K @ 30 °C
>580 °C
-4013 kJ/mole
67 kJ/mol
Safety Information
II
6.1
UN 3439 6.1/PG 2
1
25-23/24/25
36/37/39-45-28A
TI8575000
T
Separated from strong oxidants and food and feedstuffs.
Stable. Incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.
P264-P301 + P310
H300
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.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
|Danger|H300 (26.16%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 172 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P301+P310, P307+P311, P314, P321, P330, P405, and P501|P260, P264, P270, P301+P310, P307+P311, P321, P330, P405, and P501
Use dry powder, carbon dioxide, foam.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from strong oxidants and food and feedstuffs.
A harmful concentration of airborne particles can be reached quickly when dispersed.
The substance may cause effects on the central nervous system.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
PREVENT DISPERSION OF DUST!
Use local exhaust or breathing protection.
Protective gloves.
Wear safety goggles.
Toxicity
LD50 Rat ip 62 mg/kg|LD50 Mouse oral 65 mg/kg|LD50 Mouse ip 25 mg/kg|LD50 Mouse subcutaneous 46 mg/kg
1,2-Benzenedicarbonitrile's production and use as an intermediate in organic synthesis (esp, pigments and dyes) and as a base material for high temperature lubricants and coatings(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 82(SRC), determined from a log Kow of 0.99(2) and a regression-derived equation(3), indicates that 1,2-benzenedicarbonitrile is expected to have high mobility in soil(SRC). Volatilization of 1,2-benzenedicarbonitrile from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 1,2-Benzenedicarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.75X10-2 mm Hg(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 82(SRC), determined from a log Kow of 0.99(2) and a regression-derived equation(3), indicates that 1,2-benzenedicarbonitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), a range of BCF values of 0.8 to <5.5 for carp(6), suggests the potential for 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), 1,2-benzenedicarbonitrile, which has a vapor pressure of 3.75X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase 1,2-benzenedicarbonitrile 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 356 days(SRC), calculated from its rate constant of 4.5X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of 1,2-benzenedicarbonitrile with photochemically-produced hydroxyl radicals has been estimated as 4.51X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 356 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 1,2-Benzenedicarbonitrile is expected to undergo slow abiotic hydrolysis based upon the slow hydrolysis of benzonitrile under neutral conditions(2,3). 1,2-Benzenedicarbonitrile is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm)(SRC).
5.01|BCF values ranged from 0.8 to <5.5 for carp (Cyprinus carpio) exposed to 1,2-benzenedicarbonitrile (0.02 and 0.2 mg/l, respectively) for 6 weeks(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).
The Koc of 1,2-benzenedicarbonitrile is estimated as 82(SRC), using a measured log Kow of 0.99(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,2-benzenedicarbonitrile is expected to have high mobility in soil(SRC).
The Henry's Law constant for 1,2-benzenedicarbonitrile is estimated as 5.0X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,2-benzenedicarbonitrile is expected to be essentially nonvolatile from moist soil and water surfaces(2). 1,2-Benzenedicarbonitrile is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.75X10-2 mm Hg(3).
Occupational exposure to 1,2-benzenedicarbonitrile may occur through dermal contact with this compound at workplaces where 1,2-benzenedicarbonitrile is produced or used. (SRC)
Drug Information
4(?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).
0.21 Days
... systemic cyanide poisoning is suspected.
Fresh air, rest. Refer for medical attention.
Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
COMPARISON OF 20 WORKERS (AGE 32-62) WITH POSSIBLE EXPOSURE FOR 2-24 YR, FROM WHICH 7 SUFFERED ACUTE POISONING IN 1953-66, WITH CORRESPONDING CONTROL GROUP SHOWED NO SIGNIFICANT DIFFERENCES IN CHROMOSOMES.|MORTALITY RATE OF 221 EXPOSED WORKERS WAS INSIGNIFICANTLY GREATER THAN THAT OF INTERNAL OR EXTERNAL CONTROL GROUPS.|NO EVIDENCE FOR CHRONIC TOXICITY OF PHTHALONITRILE WAS FOUND. EXAM OF EXPOSED WORKERS FOR LEUKOSIS OR CARCINOGENIC EFFECTS, CLINICAL & NEUROLOGICAL EXAM OF 81 EXPOSED WORKERS, EEG STUDIES OF WORKERS GAVE RESULTS WITHIN NORMAL LIMITS.
1,2-benzenedicarbonitrile
The substance can be absorbed into the body by inhalation and by ingestion.
Dizziness. Headache. Nausea. Vomiting. Convulsions. Unconsciousness.
Phthalonitrile Use and Manufacturing
After phthalimide reacts with ammonia to obtain phthalic acid amide, it is dehydrated to obtain phthalonitrile. In addition, the product can be obtained by ammoniating phthalic anhydride and then reacting with phosphorus oxychloride, or performing ammoxidation of naphthalene pentaamine, or performing ammoxidation of o-xylene and ammonia.
Dye intermediate. Organic Synthesis.
Pigments
Agricultural products (non-pesticidal)
Paint and coating manufacturing|1,2-Benzenedicarbonitrile: ACTIVE|HIGHLY TOXIC STOMACH POISON FOR CATERPILLARS & DIPTEROUS LARVAE.
Computed Properties
Molecular Weight:128.13
XLogP3:1
Hydrogen Bond Acceptor Count:2
Exact Mass:128.037448136
Monoisotopic Mass:128.037448136
Topological Polar Surface Area:47.6
Heavy Atom Count:10
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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