HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzoic Acid
OCBA · O-CHLOROBENZOIC ACID · 2-CBA · 2-chlorobenzoic · 2-chlorobenzoate · 2-Chlorobenzoic acid, 99% · NSC 32737 · NSC 15042
Identifiers & Physical Properties
| CAS No. | 118-91-2 |
|---|---|
| Molecular formula | C7H5ClO2 |
| Average molar mass | 156.56 g/mol |
| Monoisotopic mass | 155.99780708 g/mol |
| SMILES | O=C(O)c1ccccc1Cl |
| InChIKey | IKCLCGXPQILATA-UHFFFAOYSA-N |
| PubChem CID | 8374 |
| ChEMBL | CHEMBL115243 |
| ChEBI | CHEBI:30793 |
| EC No. | 204-285-4 |
| DTXSID | DTXSID4024771 |
Chemical & Physical Properties
| XLogP | 2.1 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 136 |
| Chemical classes | Other Classes -> Benzoic Acid Derivatives |
| SpringerMaterials Properties | Chemical shift |
| Pesticides | Environmental transformation -> Pesticide transformation products (metabolite, successor) |
| LogP (partition coefficient) | log Kow= 2.052.21 |
| Density | 1.544 at 68 °F (NTP, 1992) - Denser than waterwill sink1.544 AT 20 °C/4 °C |
| Color/Form | MONOCLINIC PRISMS FROM WATER |
| Solubility | less than 1 mg/mL at 68 °F (NTP, 1992)SOL IN 900 PARTS COLD WATERMORE SOL IN HOT WATERFREELY SOL IN ALCOHOL, ETHER.SOL IN ACETONE, BENZENESOLUBLE IN METHANOL2087 mg/l at 25 °C in watercold water: soluble900 partsoluble in hot water |
| Boiling point | Sublimes (NTP, 1992)285 °C |
| Melting point | 288 °F (NTP, 1992)142 °C138-140 °C (lit.) |
| Vapor pressure | 0.00066 [mmHg]6.6X10-4 mm Hg at 25 °C (extrapolated)0.001 hPa (25 °C) |
| Physical Description | Crystals or fine fluffy white powder. (NTP, 1992)Solid[Merck Index] White powder[MSDSonline] |
| Dissociation Constants | PKA 2.89 |
| Refractive index | 1.5812 (estimate) |
| Flash point | 173 °C |
| Storage conditions | Store below +30°C. |
| pKa (acidity coefficient) | 2.92(at 25℃) |
| Physical state | Powder |
| Color | White to off-white |
| pH | 3.4 (0.2g/l, H2O, 20℃) |
| Merck | 14,2124 |
| BRN | 907340 |
| Henry's law constant | 1.5×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stability | Stable, combustible. Incompatible with strong bases, strong oxidizing agents. |
| InChI | 1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) |
| InChIKey | IKCLCGXPQILATA-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccccc1Cl |
| CAS DataBase Reference | 118-91-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 8P0867193V |
| NIST Chemistry Reference | Benzoic acid, 2-chloro-(118-91-2) |
| EPA Substance Registry System | o-Chlorobenzoic acid (118-91-2) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319 |
| GHS precautionary statements | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 |
| Hazard symbols | Xi |
| Risk statements (R) | 36-36/37/38 |
| Safety statements (S) | 26-37/39 |
| Water hazard class (WGK) | 2 |
| RTECS number | DG4976000 |
| Autoignition temperature | 530 °C |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29163900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| Hazardous substances data | 118-91-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2465 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | WarningH302 (17.1%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 222 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| Regulatory information | Chemical: Benzoic acid, 2-chloro-Commission Regulation (EC) No 33/2008Status: Active Update: 09-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/200162-Chlorobenzoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Fire hazards | Flash point data for this compound are not availablehowever, it is probably combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms resulting from exposure to this chemical include skin and eye irritation. |
| Hazards summary | A skin, eye, mucous membrane, and upper respiratory tract irritant[CAMEO] An irritant[MSDSonline] |
| Reactive group | Acids, Carboxylic |
| Reactivity Profile | O-CHLOROBENZOIC ACID is incompatible with strong oxidizing agents and strong bases. (NTP, 1992) |
| Atmospheric standards | 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/ |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (17.1%) |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| First aid | 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. |
| Nonfire spill response | 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. |
| Personal Protective Equipment (PPE) | 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/ |
| Environmental fate | 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). |
| Effluent Concentrations | o-Chlorobenzoic acid was detected in chlorinated municipal sewage effluent at a concentration of 0.3 ppb(1). |
| Soil Adsorption/Mobility | 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). |
| Natural Pollution Sources | o-Chlorobenzoic acid is an anthropogenic compound and it is not known to occur in nature. (SRC) |
| Artificial Pollution Sources | 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). |
| Environmental Biodegradation | In a survey of standarized tests, o-chlorobenzoic acid was found to biodegrade in the coupled units test, the Zahn-Wellens test, the MITI test, the Sturm test, the OECD screening test and the trickling filter test but not in the closed bottle test or the AFNOR test(1-4). o-Chlorobenzoic acid was listed as a compound amenable to biodegradation under aerobic conditions(5). o-Chlorobenzoic acid at a concn of 100 mg/L underwent oxidation, as measured by oxygen uptake, when inoculated with microorganisms isolated from soil, compost, or mud obtained from a catalytic cracking plant waste lagoon(6). It underwent 100% removal after 96 hrs when incubated with a mixed microbial seed under aerobic conditions(7). o-Chlorobenzoic acid at a concn of 16 mg/L had a lag perod of 25 days when treated with wastewater sludge supernatant and 14-25 days when inoculated with soilin the presence of glucose, complete disappearance of 8.4 mg/L o-chlorobenzoic acid was observed within 6 days with the wastewater inoculum(8).o-Chlorobenzoic acid was found to biodegrade when incubated with an anaerobic river sediment after a lag period of 6 monthsthe lag period decreased to 2 mos when sediment from a river receiving industrial effluent was used(1). It underwent 16% theoretical gas production after a 14 day lag period when inoculated with a primary digester sludge under anaerobic conditions, time not stated(2). o-Chlorobenzoic acid displayed a 6 day lag period in a continuous flow-through bioreactor using a sewage sludge seed(3). Incubation of o-chlorobenzoic acid with a Niagara silt loam sample required >64 days for disappearance of substrate(4). o-Chlorobenzoic acid was listed as being degradation resistant using the Japanese MITI test(5,6). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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). |
| Environmental Abiotic Degradation | 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). |
| Probable Routes of Human Exposure | 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). |
| Environmental Water Concentrations | DRINKING WATER: o-Chlorobenzoic acid has been qualitatively detected in U.S. drinking water supplies(1). |
| Environmental Fate/Exposure Summary | o-Chlorobenzoic acid is an anthropogenic compound which may be released to the environment as a fugitive emission during its production, formulation or use as a perservative and chemical intermediate and may be formed and released during chlorination of wastewater. If released to soil, o-chlorobenzoic acid is expected to biodegrade under both aerobic and anaerobic conditions, although there may be a lengthy lag periods. It is not expected to significantly volatilize from either moist or dry soil to the atmosphere. o-Chlorobenzoic acid is expected to display moderate to high mobility in soil, and it will be found predominately in the dissociated form in moist soil under environmental conditions. 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. o-Chlorobenzoic acid may undergo direct photolytic degradation in water. It is not expected to significantly volatilize from water to the atmosphere, nor is it expected to significantly adsorb to sediment and suspended organic matter. o-Chlorobenzoic acid will be found predominately in the dissociated form in water under the typical pH's found in the environment. If released to the atmosphere, o-chlorobenzoic acid may undergo a slow gas-phase reaction with photochemically produced hydroxyl radicals with an estimated half-life of 28.5 days. o-Chlorobenzoic acid may also undergo atmospheric removal by wet deposition processes. Occupational exposure to o-chlorobenzoic acid may occur by dermal contact during its production, formulation or use. The general population may be exposed to o-chlorobenzoic acid by the ingestion of contaminated drinking water. (SRC) |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | DG4976000 |
| Customs code | 29163900 |
| Toxicity | LD50 orally in Rabbit: 2465 mg/kg |
| Risk statements (R) | 36-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-37/39 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| Autoignition temperature | 530 °C |
| GHS precautionary statements | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 |
| Hazardous substances data | 118-91-2(Hazardous Substances Data) |
Applications & Uses
Description
2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.
Uses
2-Chlorobenzoic acid was used to study the degradation of 2-bromobenzoic acid by Pseudomonas aeruginosa.
Uses
The toxicity of halogenated benzoic acids was found to be directly related to the compound's hydrophobicity. Toxicity and quantitative structure-activity relationships of benzoic acids to Pseudokirchn eriella subcapitata.
Uses
Preservative for glues, paints. Intermediate in the manufacture of fungicides and dyes.
General Description
Crystals or fine fluffy white powder.
Preparation & Synthesis
Preparation
It is prepared by the oxidation of 2-chlorotoluene. The laboratory scale reaction employs potassium permanganate. Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene.The chloride is readily replaced by ammonia to 2-aminobenzoic acid. At elevated temperature it decarboxylates.