3-Nitrobenzoic acid

167.12

167.12

908644

204-508-5

H318ZW7612

9801

DTXSID0025737

Monoclinic leaflets or prisms|Yellowish white crystals

29163900

83.1

1.8

Slightly green to light yellow Crystals or Powder

1.494 g/cm³

142 °C

295.67°C (rough estimate)

190 °C

1.6280 (estimate)

H2O: <0.01 g/100 mL at 18 ºC

Storage temperature: no restrictions.

3.71X10-5 mm Hg at 25 deg C (est)

5.76 (vs air)

Bitter taste

Henry's Law constant = 3.79X10-10 atm-cu m/mol at 25 °C (est)

K at 25 °C = 3.48X10-4 /pKa = 3.46/

Heat of fusion = 29.33 kJ/mol; heat capacity = 1.035 J/g-K|UV: 3158 (Sadtler Research Laboratories Spectral Collection) /Benzoic acid, 2-nitro/

Insoluble in water.

Acids, Carboxylic

M-NITROBENZOIC ACID is incompatible with strong oxidizers. It is also incompatible with strong bases. It may react with cyanides. (NTP, 1992)

3053 kJ/mol

NONH for all modes of transport

3

22-36/37-33-36/37/38

26-24/25

DH5000000

Xn,Xi

Irritant

Stable. Combustible. Incompatible with strong oxidizing agents.

P261-P273-P305 + P351 + P338

H302-H315-H319-H335-H412

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Flash point data for this compound are not available but it is probably combustible. (NTP, 1992)

|Warning|H302 (94.95%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 99 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501

Fires involving this compound should be controlled using a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

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 ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 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 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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (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)

Combustible

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 3-Nitrobenzoic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

3-Nitrobenzoic acid was not detected in a study of municipal and industrial wastewater although detection limits were not reported(1).

AFTER ORAL ADMIN OF 25 MG OF 3-NITROBENZOIC ACID TO RATS, 16% OF DOSE WAS REDUCED; THIS REDUCTION WAS DECREASED BY PRETREATMENT WITH ANTIBIOTICS.

LD50 Mouse iv 640 mg/kg|LD50 Mouse ip 610 mg/kg|LD50 Rat iv 680 mg/kg|LD50 Rat ip 670 mg/kg

In a 90 day pre-chronic study, both F344 rats & B6C3F1 mice exposed to high concns of /meta-Nitrobenzoic acid (MNB)/ ... exhibited testicular atrophy & reduced sperm count. ... Data from a 2 wk dose-range-finding study (Task 1) were used to set exposure concns for the Task 2 continuous cohabitation study at 0.35, 0.75, & 1.5% in feed. Based on mean feed consumption & body weight, the estimated daily dosages were nearly =0.5, 1.3, & 2.8 g/kg/day. During Task 2, 4, 3, 2, & 3 animals died from causes ranging from lymphoma to ruptures to partner-inflicted wounds to a variety of infections. There was no clear relationship to MNB exposure. During Task 2, postpartum dam weights in the middle & high dose groups were nearly =5-8% & nearly =12-14% lower than controls, respectively. Male body weights were reduced only at the high dose, by nearly =9%. Daily feed consumption was increased at the high dose, by nearly =10%. Reproductive performance was impaired during Task 2. Mice in the middle & high dose groups delivered nearly =10% & 27% fewer pups/litter, respectively. At the high dose, there were 14% fewer litters/pair, & a 14% reduction in adjusted pup weight. In addition, the high dose group took from 5-7 days longer to deliver the third, fourth & fifth litters, a significant incr. The last litter was reared by the dam until weaning. Pre-weaning pup mortality was increased at the high dose: ca. half the pups died before weaning, & the remaining pups weighed 30-40% less than their respective controls. The only effect at the middle dose was a 15% reduction in male pup weight at /postnatal day/ 21. After the last litter was reared, a crossover test (Task 3) was conducted with the control & high dose mice. There was a 33% reduction in the number of mated females who delivered a litter in the group containing treated females. Pup indices were reduced only in litters from treated females: they delivered 50% fewer pups/litter, & those pups weighed nearly =10% less than their controls. After the crossover pups were delivered & evaluated, the control & high dose F0 adults were killed & necropsied. Treated female body weight was reduced by 13%, & adjusted kidney weight was nearly =7% lower in the 1.5% MNB females than in their controls. While there was no change in estrous cycle parameters or length, there were more cystic ovaries in the treated group (3/11) than in the controls (1/22). Male body weight at the high dose was reduced by nearly equal to 10% & adjusted liver weight was increased by nearly equal to 6%. Sperm indices were unchanged. The F1 mice from all dose groups were reared on the same diet that was provided their parents, & cohabited within dose groups at nearly =/postnatal day/ 74. At the high dose, there was a nearly =20% reduction in live pup number, while adjusted pup weight was reduced in the middle & high dose groups by 13% & 21%, respectively. After the F2 litters were delivered & evaluated, the F1 adults were killed & necropsied. Female body weight was reduced in the middle & high dose groups by 5% & 23%, respectively. Adjusted liver weight was increased by nearly =12% at the high dose; estrous cycle parameters were unchanged across dose groups. Male body weight was reduced by 10% & 18% in the middle & high dose groups, respectively. Adjusted kidney weight was reduced by nearly equal to 10% at the high dose only. No significant treatment-related microscopic lesions were noted in the reproductive organs of these animals. Thus, meta-nitrobenzoic acid reduced weight gain in adults & caused significant reproductive toxicity in both generations. The second generation was not clearly more affected than the first. The female appeared more sensitive than the male, &, though body weight was reduced, non-reproductive toxicities (organ weight changes, microscopic lesions) were not marked.

3-Nitrobenzoic acid's production and use as a dye intermediate(1), reagent for alkaloids and thorium(2), and in the preparation of 5-amino-2-hydroxy benzoic acid(3) 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 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that 3-nitrobenzoic acid is expected to have moderate mobility in soil(SRC). The pKa of 3-nitrobenzoic acid is 3.46(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 3-nitrobenzoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 3-Nitrobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-5 mm Hg(SRC), determined from a fragment constant method(7). Biodegradation of 3-nitrobenzoic acid by soil microflora inoculum took greater than 64 days(8), suggesting that biodegradation is a slow environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 240(SRC), determined from a log Kow of 1.83(2) and a regression-derived equation(3), indicates that 3-nitrobenzoic acid 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 3.8X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 3.46(5) indicates 3-nitrobenzoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(6). According to a classification scheme(7), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD of 42.0% in river water after 5 days(9), suggests that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-nitrobenzoic acid, which has an estimated vapor pressure of 3.7X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-nitrobenzoic acid 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 26 days(SRC), calculated from its rate constant of 6.1X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 3-nitrobenzoic acid may be removed from the air by wet or dry deposition(SRC). 3-Nitrobenzoic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 3-nitrobenzoic acid with photochemically-produced hydroxyl radicals has been estimated as 6.1X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 26 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Nitrobenzoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 3-Nitrobenzoic acid contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

7.08|An estimated BCF of 3.2 was calculated for 3-nitrobenzoic acid(SRC), using a log Kow of 1.83(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of 3-nitrobenzoic acid is estimated as 240(SRC), using a log Kow of 1.83(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-nitrobenzoic acid is expected to have moderate mobility in soil. The pKa of 3-nitrobenzoic acid is 3.46(4), indicating that this compound will existalmost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

A pKa of 3.46(1) indicates 3-nitrobenzoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces or moist soil surfaces is not expected to be an important fate process(2). 3-Nitrobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.71X10-5 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,306 workers (1,034 of these were female) were potentially exposed to 3-nitrobenzoic acid in the US(1). Occupational exposure to 3-nitrobenzoic acid may occur through dermal contact with this compound at workplaces where 3-nitrobenzoic acid is produced or used(SRC).

EXCRETED PRINCIPALLY UNCHANGED, ABOUT 10-20% REDUCED TO THE AMINOBENZOIC ACID AND ACETYLATED.

The metabolism of the nitrotoluenes was compared in hepatocytes isolated from male Fischer 344 rats. ... Metabolites were separated by reverse phase HPLC and identified by coelution with standards on HPLC, specific enzyme hydrolysis and GC-MS analysis. Metabolites from 3-nitrotoluene were 3-nitrobenzoic acid (56%), 3-nitrobenzyl alcohol (29%) and 3-nitrobenzyl alcohol glucuronide (13%) ... (expressed as percentage of total metabolism).

SYMPTOMS: Symptoms of exposure to this compound may include formation of methemoglobin, sensitization, irritation, and corneal damage. ACUTE/CHRONIC HAZARDS: This compound causes skin and eye irritation. When heated to decomposition it emits toxic fumes. (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. 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)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

3-nitrobenzoic acid

Benzoic acid, 3-nitro-: ACTIVE|Derivatives: m-Aminobenzoic acid; m-nitrobenzoyl chloride; Sulphur Red 7