2-Chlorobenzoic acid
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2-Chlorobenzoic acid
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CAS No:
118-91-2
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Formula:
C7H5ClO2
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Chemical Name:
2-Chlorobenzoic acid
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Synonyms:
Benzoic acid,2-chloro-;Benzoic acid,o-chloro-;2-Chlorobenzoic acid;2-CBA;o-Chlorobenzoic acid;NSC 15042;NSC 32737
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CAS No:
Description
PHYSICAL DESCRIPTION: Crystals or fine fluffy white powder. (NTP, 1992)
Crystals or fine fluffy white powder. (NTP, 1992)
Crystals or fine fluffy white powder. (NTP, 1992)|2-chlorobenzoic acid is a monochlorobenzoic acid having the chloro group at the 2-position. It has a role as a plant hormone and a plant metabolite. It is a monochlorobenzoic acid and a 2-halobenzoic acid. It is a conjugate acid of a 2-chlorobenzoate.
2-Chlorobenzoic acid Basic Attributes
156.566
156.57
247-558-3
8P0867193V
32737|15042
DTXSID4024771
MONOCLINIC PRISMS FROM WATER
29163900
Characteristics
37.3
2.0382
White crystals or powder
1.544 g/cm3 @ Temp: 20 °C
142 °C
287 °C
173 °C
1.583
soluble in hot water
Treasury low temperature ventilation and dry
0.00242mmHg at 25°C
PKA 2.89
Insoluble in water.
Acids, Carboxylic
O-CHLOROBENZOIC ACID is incompatible with strong oxidizing agents and strong bases. (NTP, 1992)
Safety Information
NONH for all modes of transport
2
R36/37/38
S26-S37/39
DG4976000
Xi
Stable, combustible. Incompatible with strong bases, strong oxidizing agents.
P305 + P351 + P338
H319
Flash point data for this compound are not available; however, it is probably combustible. (NTP, 1992)
|Warning|H302 (29.82%): Harmful if swallowed [Warning Acute toxicity, oral]|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|Aggregated GHS information provided by 114 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P333+P313, P363, P405, 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: 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)|Wear rubber gloves, a mask, coveralls, a body shield and self-contained breathing apparatus. /Benzoic acid/
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/
o-Chlorobenzoic acid was detected in chlorinated municipal sewage effluent at a concentration of 0.3 ppb(1).
Toxicity
LD50 Rabbit oral > 500 mg/kg.
o-Chlorobenzoic acid is an anthropogenic compound and it is not known to occur in nature. (SRC)
o-Chlorobenzoic acid is used as a preservative for glues and paints and as an intermediate in dye, fungicide, saccharin and agricultural chemicals manufacture(1-2). It may be released to the environment as a fugitive emission during its production, formulation or use(SRC). It may also enter the environment as a result of the chlorination of municipal wastewater(3).
TERRESTRIAL FATE: If released to soil, o-chlorobenzoic acid is expected to biodegrade under both aerobic and anaerobic conditions although there may be a lengthy lag period before this process ensues(1-4). Its estimated Henry's Law constant, 3.88X10-8 atm-cu m/mol(5,SRC), and its extrapolated vapor pressure, 6.6X10-4 mm Hg at 25 °C(6) indicate that it is not expected to volatilize from either moist or dry soil, respectively, to the atmosphere(SRC). Estimated soil adsorption coefficients of 65 and 310(7-9,SRC) indicate that o-chlorobenzoic acid will display moderate to high mobility in soil(10). The pKa of o-chlorobenzoic acid, 2.89 at 25 °C(11), indicates that it will be found predominately dissociated in moist soil under the typical pH's found in the environment(SRC).|AQUATIC FATE: If released to water, o-chlorobenzoic acid is expected to biodegrade under both aerobic and anaerobic conditions although there may be a lengthy lag period before this process ensues(1,2,3). Its estimated Henry's Law constant, 6.5X10-8 atm cu m/mol(4,SRC), indicates that it is not expected to significantly volatilize from water to the atmosphere(SRC). The half-life for volatilization from a model river 1 m deep, flowing at 1 m/sec with a wind speed of 3 m/sec is 1180 days(5,SRC). Estimated soil adsorption coefficients of 65 and 310(5,6,7,SRC) indicate that o-chlorobenozic acid will not significantly adsorb to sediment and suspended organic matter(SRC). The pKa of o-chlorobenzoic acid, 2.89 at 25 °C(8), indicates that it will be found predominately dissociated in water under the typical pH's found in the environment(SRC). o-Chlorobenzoic acid may undergo direct photolytic degradation in water(9,SRC).|ATMOSPHERIC FATE: If released to the atmosphere, o-chlorobenzoic acid may undergo a gas-phase reaction with photochemically produced hydroxyl radicals. An estimated rate constant of 5.625X10-13 cu cm/molec-sec(1,SRC) translates to a half-life of 28.5 days for this process(SRC). The water solubility of o-chlorobenzoic acid, 2087 mg/L at 25 °C(2), indicates that it may undergo atmospheric removal by wet deposition processes(SRC).
IRRADIATION OF O-CHLOROBENZOIC ACID EITHER BY SUNLIGHT OR BY UV LIGHT DID NOT YIELD NEUTRAL OR ALKALINE PRODUCTS.|Laboratory irradiation of o-chlorobenzoic acid in deoxygenated water using a medium pressure mercury lamp produced o-hyroxybenzoic acid and benzoic acid(1). An estimated rate constant for the gas-phase reaction of o-chlorobenzoic acid with photochemically produced hydroxyl radicals of 5.625X10-13 cu cm/molec/sec(2,SRC)translates to a half-life of 28.5 days(SRC) using an average atmospheric hydroxyl radical concn of 5X10+5 molec/cu cm(2).
10.00|Estimated bioconcentration factors of 8 and 21(SRC) obtained from o-chlorobenzoic acid's water solubility, 2087 mg/L at 25 °C(2), and octanol/water partition coefficient, 2.05(3), respectively, can be obtained using a appropriate regression equation. These values indicate that it will not significantly bionconcentrate in fish and aquatic organisms(SRC).
Estimated soil adsorption coefficients of 65 and 310(1,SRC) obtained from o-chlorobenzoic acid's water solubility, 2087 mg/L at 25 °C(2), and octanol/water partition coefficient, 2.05(3), respectively, can be obtained using an appropriate regression equation. These values indicate that it will display moderate to high mobility in soil(4).
The extrapolated vapor pressure of o-chlorobenzoic acid, 6.6X10-4 mm Hg at 25 °C(1) indicates that it is not expected to significantly volatilize from dry soil(SRC). Its estimated Henry's Law constant, 3.88X10-8 atm cu m/mol(2,SRC), indicates that it will not significantly volatilize from either water or moist soil(SRC). Based on this value, the estimated half-life for volalitilization from a model river 1 m deep, flowing at 1 m/sec and a wind speed of 3 m/sec is 1180 days(3,SRC).
DRINKING WATER: o-Chlorobenzoic acid has been qualitatively detected in U.S. drinking water supplies(1).
Occupational exposure to o-chlorobenzoic acid may occur by dermal contact during its production, formulation or use(SRC). Exposure to the general population may occur by ingestion of contaminated drinking water(SRC), as it has been detected in drinking water supplies(1).
Drug Information
EXPTL USE: OF THE 16 BENZOIC ACID DERIVATIVES TESTED, O-CHLOROBENZOIC ACID, PHENYLACETIC ACID, & PARTICULARLY BENZOIC ACID SHOWED THE HIGHEST ANTI-ULCER ACTIVITY IN RATS WITH SHAY ULCERS & RESERPINE-INDUCED GASTRIC ULCERS.
YIELDS CATECHOL IN PSEUDOMONAS; YIELDS O-CHLOROBENZOYL-BETA-D-GLUCURONIC ACID & O-CHLOROHIPPURIC ACID IN RABBITS. /FROM TABLE/
SYMPTOMS: Symptoms resulting from exposure to this chemical include skin and eye 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. When heated to decomposition this compound 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)
2-chlorobenzoate
2-Chlorobenzoic acid Use and Manufacturing
1. With phthalic anhydride as raw material and sodium hydroxide and ammonia for amidation and degradation reaction prepared o-aminobenzoic acid, and then with sodium nitrite, hydrochloric acid diazotization, and then copper chloride, hydrochloric acid replacement and prepared O-chlorobenzoic acid crude, refined after the finished product.
2. o-chlorotoluene chloride hydrolysis in the system.
3. The preparation method has the following two kinds. O-chlorotoluene chloride hydrolysis o-chlorotoluene placed in the reactor, with ultraviolet light, the reaction temperature of 100 ° C, chlorine into the chlorination reaction to deepen the depth of chlorination to produce α, α, α, Chlorinated toluene, or o-chlorotoluene as raw material, azobisisobutyronitrile as a catalyst for chlorination, can also be α, α, α, 2-tetrachlorotoluene, and then the product into the hydrolysis kettle, add a little acid So that hydrolysis of o-chlorobenzoyl chloride, hydrolysis depth can be obtained 2-chlorobenzoic acid. O-aminobenzoic acid diazotization method to o-aminobenzoic acid as raw material by adding hydrochloric acid, sodium nitrite diazotization, and then in the diazo solution by adding Cu2Cl2 dissolved in hydrochloric acid solution, while stirring side by side, after treatment O-chlorobenzoic acid.
Preservative for glues, paints, intermediate in manufacture of fungicides & dyes.
(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
Benzoic acid, 2-chloro-: ACTIVE
Environmental transformation -> Pesticide transformation products (metabolite, successor)
M02 2-chlorobenzoic acid is a known environmental transformation product of Clofentezine, Clomazone, and Prothioconazole.
Computed Properties
Molecular Weight:156.56
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.9978071
Monoisotopic Mass:155.9978071
Topological Polar Surface Area:37.3
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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