4-Chlorobenzoic acid

156.57

156.57

907196

200-805-9

IC7888DF4L

0503

32738|8444

TSCA listed

DTXSID9024772

White to yellow

29163900

284nm(EtOH)(lit.)

37.30000

2.7

Triclinic crystals or light fluffy white powder. (NTP, 1992)

1.540

238-241 °C(lit.)

274-276 °C

127.5±19.8 °C

1.5812 (estimate)

soluble in hot water

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

2.92X10-5 mm Hg at 25 deg C (est)

Relative vapour density (air = 1): 5.4

LD50 orally in Rabbit: 1170 mg/kg

4.3 (0.08g/l, H2O, 20℃)

3.98(at 25℃)

2.5×101mol/(m3Pa) at 25℃, Abraham and Jr. (2019)

3.98 (at 25 °C)|pKa = 3.98|pKa = 4.03

127.6 Ų [M-H]-

White, odorless, crystalline powder, freely soluble in water /p-Chlorobenzoic acid, sodium salt/|Nearly white, course powder. Soluble in methanol, alcohol, ether, and hot water /Chlorobenzoic acid/|Hydroxyl radical reaction rate constant = 1X10-12 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Acids, Carboxylic

4-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.

545 °C

room temp

NONH for all modes of transport

2

Xn

26-36-37/39

DG4976010

Xn:Harmful

Stable. Combustible. Incompatible with bases, strong oxidizing agents.

P301 + P312 + P330

22-36/37/38

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents, strong bases.

Flash point data for 4-Chlorobenzoic acid are not available; however, 4-Chlorobenzoic acid is probably combustible.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 105 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501

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 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% 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 60-70% 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 chemical under refrigerated temperatures, and keep it away from oxidizing materials. (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)|Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Special hazards arising from the substance or mixture: Carbon oxides, hydrogen chloride gas.

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached when dispersed.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety spectacles.

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. Chlorobenzoic acid is produced, as an intermediate or final product, by process units covered under this subpart. /Chlorobenzoic acid/

p-Chlorobenzoic acid was detected, not quantified in 6 out of 18 samples of advanced treatment concentrate collected from Lake Tahoe, CA, Oct 1974; Pomona, CA, Sept 1974; Escondido, CA July 1975; and Dallas, TX, Nov 1974(1). p-Chlorobenzoic acid was detected in the emissions of a municipal waste incineration plant in Germany at a concentration of 1.16 ug/cu m(2).

SEDIMENT: p-Chlorobenzoic acid was detected, not quantified in contaminated sediment enrichments collected from Bloody Run Creek and Devil's Hole Creek, located in the Niagara River watershed, Niagara Falls, NY. Samples were collected during May and November 1992 and May, August, November 1993(1).

IDENTIFICATION AND USE: P-chlorobenzoic acid is white, odorless, crystalline powder. It is used as a laboratory reagent, and in manufacture of chemicals. P-Chlorobenzoic acid is a degradation product of indomethacin. HUMAN EXPOSURE AND TOXICITY: No human studies could be located. ANIMAL STUDIES: P-Chlorobenzoic acid is a potent inhibitor of rat brain and liver mitochondrial 4-hydroxybenzoate:polyphenyl transferase. After single oral administration to animals urokaninase and histidase activities were found in blood serum within 8 hr after the intoxication, reaching the maximum within 15 hr and exhibited the constant level during 25 hr. Then the enzymatic activity was gradually decreased but it did not reach the control values within 70 hr.

LD50 Mouse oral 1170 mg/kg|LD50 Rat ip 1000 mg/kg|LD50 Rat oral 1170 mg/kg

p-Chlorobenzoic acid's production and use as a laboratoryy reagent and chemical intermediate(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 42(SRC), determined from a log Kow of 2.65(2) and a regression-derived equation(3), indicates that p-chlorobenzoic acid is expected to have very high mobility in soil(SRC). The pKa of p-chlorobenzoic acid is 3.98(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 from moist soil is not expected because the compound exists as an anion and anions do not volatilize(SRC). p-Chlorobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(3). Using an activated sludge inoculum, 6% CO2 evolution after 5 days incubation(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 2.65(2) and a regression-derived equation(3), indicates that p-chlorobenzoic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.98(4) indicates p-chlorobenzoic 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(SRC). The BCF for p-chlorobenzoic acid was < 10 in golden ide fish(5), which suggests the potential for bioconcentration in aquatic organisms is low(SRC). A range of 2.03% to 79% 14-CO2 recovered using varying concentrations in the river die-away test(6) suggests that biodegradation may be an important environmental fate process in water, subject to conditions(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-chlorobenzoic acid, which has an estimated vapor pressure of 2.9X10-5 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 p-chlorobenzoic 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 10 days(SRC), calculated from its rate constant of 1X10-12 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase p-chlorobenzoic acid may be removed from the air by wet and dry deposition(SRC). p-Chlorobenzoic acid absorbs light 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 p-chlorobenzoic acid with photochemically-produced hydroxyl radicals has been estimated as 1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). p-Chlorobenzoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). p-Chlorobenzoic acid absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The BCF in golden ide (Leuciscus idus melanotus) fish was reported to be < 10 in a 3-day experiment(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of p-chlorobenzoic acid is estimated as 42(SRC), using a log Kow of 2.65(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that p-chlorobenzoic acid is expected to have very high mobility in soil. The pKa of p-chlorobenzoic acid is 3.98(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).

A pKa of 3.98(1) indicates p-chlorobenzoic 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(SRC). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize(SRC). p-Chlorobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-3 mm Hg(SRC), determined from a fragment constant method(3).

GROUNDWATER: p-Chlorobenzoic acid was detected, not quantified in groundwater from the Hyde Park chemical landfill site that was the source of contaminated sediment in Bloody Run Creek and Devil's Hole Creek, located in the Niagara River watershed, Niagara Falls, NY. Samples were collected during May and November 1992 and May, August, November 1993(1).|DRINKING WATER: p-Chlorobenzoic acid was qualitatively detected in 4 of 16 samples of drinking water concentrate derived from large volume (>400 gallons) samples from 4 of 7 cities (New Orleans, LA, Jan 1976; Philadelphia, PA, Feb 1976; Poplarville, MS, Mar 1979; and Cincinnati, OH, Oct 1978)(1).

Occupational exposure to p-chlorobenzoic acid may occur through inhalation and dermal contact with this compound at workplaces where p-chlorobenzoic acid is produced or used. Limited monitoring data indicate that the general population may have been exposed to p-chlorobenzoic acid via dermal contact with and ingestion of contaminated drinking water. (SRC)

P-chlorobenzoyl-beta-d-glucuronic acid in rabbit. /From table/|Yields p-chlorohippuric acid in man. /From table/|Pseudomonas sp. WR912 was isolated by continuous enrichment in three steps with 3-chloro-, 4-chloro-, and finally 3,5-dichlorobenzoate as sole source of carbon and energy. The doubling times of the pure culture with these growth substrates were 2.6, 3.3, and 5.2 h, respectively. Stoichiometric amounts of chloride were eliminated during growth. Oxygen uptake rates with chlorinated benzoates revealed low stereospecificity of the initial benzoate 1,2-dioxygenation. Dihydrodi-hydroxybenzoate dehydrogenase, catechol 1,2-dixoygenase, and muconate cycloisomerase activities were found in cell-free extracts. The ortho cleavage activity for catechols appeared to involve induction of isoenzymes with different stereospecificity towards chlorocatechols. A catabolic pathway for chlorocatechols was proposed on the basis of similarity to chlorophenoxyacetate catabolism, and cometabolism of 3,5-dimethylbenzoate by chlorobenzoate-induced cells yielded 2,5-dihydro-2,4-dimethyl-5-oxo-furan-2-acetic acid.|A mixed population, enriched and established in a defined medium, from a sewage sludge inoculum was capable of complete mineralization of 4-chlorobenzoate. An organism, identified as Arthrobacter sp., was isolated from the consortium and shown to be capable of utilizing 4-chlorobenzoate as the sole carbon and energy source in pure culture. This organism (strain TM-1), dehalogenated 4-chlorobenzoate as the initial step in the degradative pathway. The product, 4-hydroxybenzoate, was further metabolized via protocatechuate. The ability of strain TM-1 to degrade 4-chlorobenzoate in liquid medium at 25 °C was improved by the use of continuous culture and repeated sequential subculturing. Other chlorinated benzoates and the parent compound benzoate did not support growth of strain TM-1. An active cell extract was prepared and shown to dehalogenate 4-chloro-, 4-fluoro-, and 4-bromobenzoate. Dehalogenase activity had an optimum pH of 6.8 and an optimum temperature of 20 °C and was inhibited by dissolved oxygen and stimulated by manganese (Mn). Strain improvement resulted in an increase in the specific activity of the cell extract from 0.09 to 0.85 nmol of 4-hydroxybenzoate per min per mg of protein and a decrease in the doubling time of the organism from 50 to 1.6 hr.

Octanoate, salicylate, valproic acid, p-octyl-, p-nitro-, and p-chlorobenzoic acids were effective inhibitors of benzoic acid activation to benzoyl-CoA by mitochondrial extracts. p-Aminobenzoic acid was much less effective. Of these compounds, only salicylate and p-nitrobenzoic acid were not activated to their respective CoA esters. Salicylate, p-chloro- and p-nitrobenzoic acids effectively prevented inhibition of glucose synthesis and alpha-keto[1-(14)C]isovalerate oxidation by valproic acid, p-octyl-, and p-aminobenzoic acids, p-Octyl- and p-aminobenzoic acids greatly depleted hepatocyte free CoA and acetyl-CoA contents and increased the content of acid-insoluble and acid-soluble CoA esters respectively. p-Chloro- and p-nitrobenzoic acids prevented the sequestration of CoA as p-octylbenzoyl-CoA or p-aminobenzoyl-CoA in hepatocytes incubated with these compounds. p-Chlorobenzoic acid not only prevented but also reversed the inhibition of gluconeogenesis in hepatocytes incubated with p-octylbenzoic acid. These results suggest that p-chloro- or p-nitrobenzoic acids might be effectively used to reverse some of the hepatotoxic effects of the CoA esters of valproic acid or naturally-occurring organic acids, such as those which accumulate in Reye's Syndrome or organic acidemias.

SYMPTOMS: Symptoms resulting from exposure to this compound include eye and skin irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is irritating to eyes, skin, mucous membranes and the upper respiratory tract. Decomposition produces toxic gases. (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)

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Organic acids and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. 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 ... . 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|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. Early intubation, at the first sign of upper airway obstruction, may be necessary. 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 (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

4-chlorobenzoate

The substance can be absorbed into the body by ingestion.

Benzoic acid, 4-chloro-: ACTIVE

A densitometric method was developed for the identification and determination of indomethacin and its degradation products, 4-chlorobenzoic acid and 5-methoxy-2-methyl-3-indoleacetic acid, in pharmaceuticals. To separate these compounds, silica gel-coated thin-layer chromatography plates and the following mobile phase were used: 2-propanol-25% ammonia-water (8 + 1 + 1, v/v). UV densitometric measurements were made by comparing the absorption spectra and Rf values of appropriate standards with the pharmaceutical preparations examined. The conditions for separation were established and a low detection limit was obtained. Average recoveries were 100.69, 90.09, and 91.17% for indomethacin, 4-chlorobeznzoic acid, and 5-methoxy-2-methyl-3-indoleacetic acid, respectively.|The infrared, the Fourier transform infrared and Fourier transform Raman spectra of p-chlorobenzoic acid (p-CBA) has been recorded in the region 4000-600 cm(-1), 4000-400 cm(-1) and 4000-100 cm(-1), respectively. The optimized geometry, frequency and intensity of the vibrational bands of p-CBA were obtained by the ab initio HF and DFT (B3LYP) methods with complete relaxation in the potential energy surface using 6-311+G(d,p) basis set. The harmonic-vibrational frequencies were calculated and the scaled values have been compared with experimental FT-IR and FT-Raman spectra. The observed and the calculated frequencies are found to be in good agreement. The experimental spectra also coincide satisfactorily with those of theoretically constructed bar type spectrograms.

Environmental transformation -> Pesticide transformation products (metabolite, successor)

S3 (4-chlorobenzoic acid) is a known environmental transformation product of Hexythiazox and Valifenalate.